Name: 1402838-08-7|2-(1-Trityl-4-imidazolyl)benzaldehyde|95%
Brand: Ambeed
SKU: A581640
Rating: 98 (28 reviews)

1
[ 40138-16-7 ]
[ 96797-15-8 ]
[ 1402838-08-7 ]

Yield	Reaction Conditions	Operation in experiment
75.6%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	2-formylbenzeneboronic acid (1.55 g, 6.88 mmol),1-trityl-4-iodoimidazole (3.0 g, 4.59 mmol),Potassium phosphate (4.38 g, 13.77 mmol),Pd(PPh3)4 (0.3g, 10%, w/w%) was added to DMF (30mL)In a mixed solution with water (6 mL), the system was replaced with nitrogen 4 times.The reaction was carried out at 90 C overnight under a nitrogen atmosphere. TLC detects complete reaction,Cooled to room temperature, filtered and the filtrate was diluted with ethyl acetate (300 mL).Wash three times with water (100 mL), and dilute the organic phase under reduced pressure.The residue is separated by flash column chromatography.The target product was 2.15g,The yield was 75.6%.
72%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	A mixture of 4-iodo-1-(triphenylmethyl)-1H-imidazole (Intermediate A, 4.36 g, 9.99 mmol), (2-formylphenyl)boronic acid (1.65 g, 11.00 mmol), Pd(PPh3)4 (1.16 g, 1.0 mmol) and K3PO4 (4.25 g, 20.02 mmol) in DMF (40 mL) and water (8 mL) was stirred at 100 C. for 16 h under N2 atmosphere. The reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (150 mL*2). The organic phases were combined, washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with EtOAc in hexane (1% to 25% gradient) to yield 2-(1-trityl-1H-imidazol-4-yl)benzaldehyde as yellow solid (3 g, 72%). MS: m/z=415.1 [M+H]+.
66.7%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	A suspensionof 4 (3.0 g, 6.9 mmol), the appropriate 2-formyl boronic acid(1.6 g, 10.7 mmol) and K3PO4 (4.4 g, 20.8 mmol) in DMF (30 mL) andwater (6 mL) was purged with nitrogen for 5 min, followed by theaddition of Pd(PPh3)4 (0.6 g, 0.5 mmol) and the mixturewas purgedwith nitrogen for another 5 min. The reaction mixture was stirredat 90 C for 16 h under an atmosphere of N2. The solution wasallowed to cool and was filtered through a plug of celite. Themixture was diluted with water (50 mL) and was extracted withethyl acetate to afford the crude product which was purified byflash column chromatography on silica gel to yield 6 as a white solid(1.9 g, 66.7%). Mp 147e149 C. 1H NMR (300 MHz, Chloroform-d)d(ppm) 7.97 (dd, J 7.8, 1.4 Hz, 1H), 7.72e7.54 (m, 3H), 7.38 (h,J 3.2 Hz,11H), 7.25e7.19 (m, 6H), 7.07 (d, J 1.3 Hz, 1H). MS (EI) m/z 415.2 [MH].

66.7%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	3 (3.0 g, 6.9 mmol),Formylbenzeneboronic acid (1.6 g, 10.7 mmol),K3PO4 (4.4 g, 20.8 mmol) was dissolved in DMF (30 mL) and water (6 mL)Pd (PPh3) 4 (0.6 g, 0.5 mmol) was added,N2 protection at 90 C for 16 hours,Cooling, suction filtration,Water (50 mL) was added, extracted with ethyl acetate,Dried over anhydrous magnesium sulfate,Column chromatography gave a white solid,Yield 66.7%
63%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	General procedure: 4-Iodo-1-trityl-1H-imidazole (5, 2 g, 4.58 mmol), (5-chloro-2-methoxyphenyl)boronic acid(0.852 g, 4.58 mmol), K3PO4 (2.9 g, 13.7 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) were added todry dimethylformamide (30 mL). The reaction mixture was stirred at 100 C under inert atmosphere,until the starting material disappeared in TLC. The reaction mixture was distilled in vacuo, and ethylacetate (100 mL) was added to the mixture. The organic extract was washed twice with saturatedaqueous NaCl (20 mL), and the organic extract was dried over Na2SO4. After solvent was removedunder vacuum, the product was purified as a white solid by silica gel column chromatography, 1.2 g,yield 63%.
60%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	[270] To a solution of (2-forrnylphenyl)boronic acid (2.0 g, 13.3 rnrnol) in a rnixed solvent of N,N- dirnethylforrnarnide (DMF) (60 rnL) and water (12 rnL) was successively added 4-iodo-1- trityl-1H-irnidazole (6.1 g, 14.0 rnrnol), and potassiurn phosphate (5.6 g, 26.6 rnrnol). After degassing with nitrogen, the resulted rnixture was added tetrakis(triphenylphosphine)palladiurn(0) (Pd(PPh3)4) (300 rng, 0.26 rnrnol). The resulted rnixture was degassed with nitrogen and stirred at 90C for overnight under nitrogen. And then the rnixture was cooled down to roorn ternperature and filtered, the filtrate was added water (60 rnL), extracted with ethyl acetate (100 rnLx2). The cornbined organic phase was washed with brine (25 rnL), dried over sodiurn sulfate, filtered and concentrated. The residue was purifiedby colurnn chrornatography on silica gel (petroleurn ether: ethyl acetate= 6:1) to afford cornpound 1.1 (3.3 g, yield: 60%) as a white solid.[271] rn/z: [M+H]415
54%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃; for 6h;Inert atmosphere;	Under nitrogen protection,Tetrakistriphenylphosphine palladium (2.0 g, 1.7 mmol, 0.074 eq), 4-iodo-1-trityl-1H-imidazole (0102-1) (10.0 g, 23.0 mmol, 1.0 eq),2-aldehyde phenylboronic acid (0103-1) (4.1 g, 27.5 mmol, 1.2 equiv) andTripotassium phosphate (12.0 g, 46 mmol, 2.0 equiv)Add to a mixture of 180 ml of dimethylformamide and water (5:1),Heat to 90C and react for 6 hours.Cool to room temperatureAfter suction filtration through Celite, the resulting filtrate was diluted with ethyl acetate to 1000 ml, washed with saturated brine three times, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography (eluent: petroleum ether: ethyl acetate. Ester = 8:1 and petroleum ether: dichloromethane = 2:1),2-(1-trityl-1H-imidazol-4-yl)benzaldehyde (5.2 g, yield: 54%) was obtained as a white solid.
52%	With K3PO4;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	Example 3 Suzuki Cross-Coupling of 4-Iodo-l-trityl-lH- imidazole with PhenylboronicAcids[0138] A suspension of 4-iodo-l-trytyl-lH- imidazole (6.88 mmol ), the appropriate 2-formyl boronic acid derivative (10.31 mmol) and K3PO4 (20.63 mmol) in N,N-dimethylformamide (30 mL) and water (6 mL) was purged with nitrogen for 5 minutes, followed by the addition of Pd(PPh3)4 and the mixture was purged with nitrogen for another 5 minutes. The reaction mixture was stirred at 90 C for 16 h under an atmosphere of 2.The solution was allowed to cool and was filtered through a plug of celite. The mixture was diluted with water (50 mL) and EtOAc (25 mL). The organic layer was collected and the aqueous layer was extracted with EtOAc (2 x 25 mL). The combined organic extracts were washed with water (2 x 25 mL), brine and dried ( a2S04). The solution was filtered and the solvent was removed under reduced pressure to afford the crude product which was purified by flash column chromatography on silica gel to provide the following compounds.No. Compound Name Yield (%)JH NMR(MeOH-d4) 7.16-7.27 (m, 6H), 7.29-7.47 (m, 3H), 7.60-7.70 (m, 9H), 7.85- 7.90 (m, 2H), 10.26 (s, 1H)
40.8%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 90℃; for 16h;Inert atmosphere;	4-iodo-1-trityl-1H-imidazole (38.7 g, 88.8 mmol), (2-formylphenyl)boronic acid (20.0 g, 133 mmol)And K3PO4 (56.4 g, 266 mmol) was dissolved in 1,4-dioxane (300 mL) and water (60 mL).Nitrogen gas was bubbled through the reaction solution for 5 min, then Pd(PPh3)4 (5.12 g, 4.44 mmol) was added, and the reaction mixture was bubbled with nitrogen for 5 min.The reaction was heated at 90 C for 16 h under nitrogen.After the reaction was completed, the temperature was lowered, and the celite was filtered, and the filtrate was diluted with water (100 mL) and EA (300 mL), and the mixture was allowed to stand for separation. The aqueous phase was extracted with EA (300 mL×2; combined organic phase, water (100 mL) and saturated brine (100 mL × 3) washing.The organic phase was concentrated under reduced pressure to give a residue.Purified with PE/EA=3/1 column,Obtained a light brown viscous oil 2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (15.0 g, 40.8%).
39%	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 90℃;Inert atmosphere;	Compound 1 (2.2 g, 5.0mmol), o-formylphenylboronic acid(1.2 g, 7.5mmol), K3PO4 (3.2 g, 15mmol), Pd (PPh3)4 (0.6 g, 1.0mmol) is dissolved in DMF/H20 (30mL/6mL). The system is replaced with nitrogen and warmed at 90C, the reaction is stirred overnight. The reaction solution is diluted with ethyl acetate (50mL), wash with saturated brine (25mL X 3), dry over anhydrous sodium sulfate, and dry under reduced pressure. Crude column chromatography (PE: EA = 5:1), and then obtained brown solid compound 2 (810 mg, 39%).
650 mg	With potassium phosphate; tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	step 1.Take a 100ml single-mouth bottle and add 300mg 2-formylbenzeneboronic acid.1090 mg 1-trityl-4-iodoimidazole, 848 mg K3PO4,23mg Pd(PPh3)4, and 2ml water, 10ml DMF,Reacting at 100 C under N2 protection overnight,Complete reactionThe mixture was poured into water, and the mixture was extracted with EtOAc.Column chromatography gave 650 mg of light gray compound 26;

Reference： [1]Patent: CN108424415,2018,A .Location in patent: Paragraph 0219; 0220; 0221; 0222
[2]Patent: US2016/75711,2016,A1 .Location in patent: Paragraph 0251-0252
[3]European Journal of Medicinal Chemistry,2017,vol. 140,p. 293 - 304
[4]Patent: CN107501272,2017,A .Location in patent: Paragraph 0085; 0086; 0093; 0094
[5]Molecules,2019,vol. 24
[6]Patent: WO2016/131380,2016,A1 .Location in patent: Paragraph 269; 270; 271
[7]Patent: CN107383024,2017,A .Location in patent: Paragraph 0113
[8]Patent: WO2012/142237,2012,A1 .Location in patent: Page/Page column 87-88
[9]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733
[10]Patent: CN108203438,2018,A .Location in patent: Paragraph 0147; 0148; 0149; 0150
[11]Patent: CN107556315,2018,A .Location in patent: Paragraph 0051-0053
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[13]Patent: CN108689958,2018,A .Location in patent: Paragraph 0143-0145

2
[ 577-59-3 ]
[ 1402838-08-7 ]
[ 1402836-61-6 ]

Yield	Reaction Conditions	Operation in experiment
16%		Example 5 General Procedure for the Synthesis of 2-(5H-imidazo[5,l-a]isoindol-5- yl)ethanones by Aldol Condensation of 2-(l-trityl-lH-imidazol-4- yl)benzaldehydes with Methyl Ketones Followed by Cyclization [0140] To a solution of the appropriate aldehyde 3-8 (0.97 mmol) and ketone (0.97 mmol) in anhydrous THF (5 mL) at rt was added NaOEt (1.25 mmol, 21 wt % solution in EtOH) and the yellow solution was allowed to stir 3 h at rt. The solvent was distilled off and the crude was diluted with saturated NH4C1 (10 mL) and the aqueous layer was extracted with dichloromethane (3 x 20 mL). The combined organic extracts were washed with brine, dried over Na2S04 and the solvent evaporated under reduced pressure to afford the crude product. To the crude imidazole from the previous step was added acetic acid (1.0 mL) and MeOH (4.0 mL). The solution was stirred at 90 C for 3-10 h. The reaction mixture was allowed to cool to room temperature and the pH was adjusted to ~10 with satd. K2CO3 (aq). The aqueous phase was extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with water, brine, and dried. The solvent was removed in vacuo to afford the crude residue, which was purified by flash column chromatography on silica gel to afford the following compounds.

Reference： [1]Patent: WO2012/142237,2012,A1 .Location in patent: Page/Page column 89-90

3
[ 1402838-33-8 ]
[ 1402838-08-7 ]
[ 1402838-66-7 ]

Yield	Reaction Conditions	Operation in experiment
93%		Example 23 General Procedure for the Synthesis of 2-(5H-imidazo[5,l-a]isoindol-5- yl)ethanones by Horner- Wadsworth-Emmons Reaction Followed by Cyclization. [0155] To a suspension of 95% NaH (17.4 mg, 0.7 mmol) in THF (3 mL) at 0 C was added the appropriate phosponate reagent 27-46, 89, 90 or 122-135 (0.75 mmol) as a solution in THF (2 mL) and the mixture was stirred for 40 min. The appropriate 2-(l-trityl-lH-imidazol- 4-yl)benzaldehyde was added as a solution in THF (3 mL) drop wise over a period of 3 min. The reaction was allowed to warm to RT and stirred overnight. The solvent was removed under reduced pressure and the crude was diluted with saturated NH4C1 (10 mL) and water (10 mL). The aqueous layer was extracted with CH2CI2 (2 x 20 mL) and the combined organic fractions were washed with brine (15 mL), dried over Na2S04 and concentrated under reduced pressure to afford the crude product. To the crude residue was added AcOH (1 mL) and MeOH (3 mL) and the solution was stirred at 90 C for 2 h. After cooling to rt, the solvent was distilled off and the crude was stirred in a mixture of sat'd K2CO3 (5 mL) and EtOAc (5 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with water, brine and dried ( a2S04) and the solvent evaporated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel to afford the following compounds.Yield

Reference： [1]Patent: WO2012/142237,2012,A1 .Location in patent: Page/Page column 108-110

4
[ 1402838-08-7 ]
[ 58009-66-8 ]
1-cyclohexyl-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		At 0 C., to a suspension of sodium hydride (60%, 348 mg, 8.7 mmol) in THF (40 mL) was added a solution of dimethyl (2-cyclohexyl-2-oxoethyl)phosphonate (1.87 g, 7.98 mmol) in THF (10 mL) slowly. After stirring for additional 15 min at 0 C., the reaction mixture was treated with a solution of <strong>[1402838-08-7]2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde</strong> (3 g, 7.24 mmol) in THF (15 mL). The resulting mixture was then stirred at room temperature for 2.5 h. The reaction was then quenched by water (100 mL) and the mixture was extracted with ethyl acetate (150 mL*2). The organic phases were combined, washed with brine, and dried over Na2SO4. The solvent was removed under reduced pressure to yield 1-cyclohexyl-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one as light yellow solid (3.5 g, 93% crude yield) which was used in next step without further purification. MS: m/z=523.2 [M+H]+.

Reference： [1]Patent: US2016/75711,2016,A1 .Location in patent: Paragraph 0251; 0253

5
dimethyl 2-(4-(tert-butyldimethylsilyloxy)cyclohexyl)-2-oxoethylphosphonate [ No CAS ]
[ 1402838-08-7 ]
1-[4-[(tert-butyldimethylsilyl)oxy]cyclohexyl]-3-[2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		At 0 C., to a suspension of sodium hydride (60% in oil, 116 mg, 2.90 mmol) in THF (10 mL) was added a solution of dimethyl (2-[4-[(tert-butyldimethylsilyl)oxy]cyclohexyl]-2-oxoethyl)phosphonate (Intermediate B, 967 mg, 2.65 mmol) in THF (5 mL) slowly. After stirring for additional 15 min at 0 C., the reaction mixture was added by a solution of <strong>[1402838-08-7]2-[1-(triphenylmethyl)-1H-imidazol-4-yl]benzaldehyde</strong> (1 g, 2.41 mmol) in THF (5 mL). The resulting reaction mixture was then stirred at room temperature for 2 h. The reaction was quenched by the addition of water (40 mL) carefully and the resulting mixture was extracted with ethyl acetate (80 mL*3). The combined organic phase was washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to yield 1-[4-[(tert-butyldimethylsilyl)oxy]cyclohexyl]-3-[2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]prop-2-en-1-one (1.4 g, 89% crude yield) as yellow oil which was used in next step without further purification. MS: m/z=653.3 [M+H]+.

Reference： [1]Patent: US2016/75711,2016,A1 .Location in patent: Paragraph 0356-0357

6
[ 1402838-08-7 ]
1-(4-phenyladamantan-1-yl)ethanone [ No CAS ]
C₄₇H₄₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium ethanolate; In tetrahydrofuran; ethanol; at 60℃; for 2h;	[979] To a solution of 1-(4-phenyladamantan-1-yl)ethanone (127 mg, 0.5 mmol) in amixed solvent of ethanol (1 mL) and THF (4 mL) was successively added sodium ethoxide(70 mg, 1.0 mmol) and compound 1.1 (414 mg, 1.0 mmol). The resulted mixture was stirred at 60C for 2h, then cooled down to room temperature. The mixture was added water (20 mL), extracted with ethyl acetate (10 mL x 2). The combined organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated, the residue was purified by columnchromatography on silica gel (petroleum ether: ethyl acetate= 3:1) to afford compound 62.2 (260 mg, yield: 80%) as a yellow solid.[980] m/z: [M+H] 65 1

Reference： [1]Patent: WO2016/131380,2016,A1 .Location in patent: Paragraph 977; 978; 979; 980

7
[ 1402838-08-7 ]
[ 1660-04-4 ]
C₄₁H₃₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium ethanolate; In tetrahydrofuran; ethanol; at 20℃;	[402] To a solution of compound 1.1 (500 mg, 1.2 mmol) and 1-(adamantan-1-yl) ethanone (235 mg, 1.3 mmol) in a mixed solvent of ethanol (5 mL) and THF (5 mL) was added sodium ethoxide (122 mg, 1.8 mmol). The resulted mixture was stirred at room temperature for overnight, then the mixture was added water (30 mL), and extracted with ethyl acetate (60 mLx2). Then the combined organic phase was washed with brine, dried oversodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate= 2:1) to afford compound 1.2 (400 mg, yield: 62%) as a white solid.[403] m/z: [M+H] 575

Reference： [1]Patent: WO2016/131380,2016,A1 .Location in patent: Paragraph 400; 401; 402; 403

8
[ 1402838-08-7 ]
1-(4-acetyladamantan-1-yl)-3-(4-cyanophenyl)urea [ No CAS ]
C₄₉H₄₃N₅O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With sodium ethanolate; In tetrahydrofuran; ethanol; at 20℃;	[1073] To a solution of 1-(4-acetyladamantan-1-yl)-3-(4-cyanophenyl)urea (406 mg, 1.2mmol) and compound 1.1 (500 mg, 1.2 mmol) in THF (30 mL) was added a solutionof sodium ethylate (163 mg, 2.4 mmol) in ethanol (5.0 mL) at room temperature. The resulted mixture was stirred at room temperature for overnight, and then the reaction was quenched by addition of cold water (25 mL), extracted with ethyl acetate (2x30 mL). The combined organic phase was washed with brine (25 mL), dried over sodium sulfate andconcentrated. The residue was purified by flash column chromatography on silica gel (050% solution of ethyl acetate in petroleum ether) to afford compound 161.2 (550 mg, yield: 62%) as a pale yellow solid.[1074] m/z: [M+H] 734

Reference： [1]Patent: WO2016/131380,2016,A1 .Location in patent: Paragraph 1071; 1072; 1073; 1074

9
[ 1402838-08-7 ]
[ 1660-04-4 ]
C₂₂H₂₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		To a stirred mixture of compound 10a (97 mg, 0.234 mmol) and compound 10b (42 mg, 0.234 mmol) in anhydrous THF (10 mL) was added dropwise a solution of EtONa (21in EtOH, 98 mg, 0.304 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h, and concentrated to dryness under reduced pressure. The residue was diluted with NH4Cl solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (8 mL) . To this solution was added HOAc (2 mL) , and the reaction mixture was stirred at 90 for 3 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (CH2Cl2: MeOH 50 : 1) to afford compound 10c (62 mg, 79yield) as a grey solid. MS 333.1 [M+H]+.

Reference： [1]Patent: WO2016/165613,2016,A1 .Location in patent: Paragraph 123

10
[ 1402838-08-7 ]
[ 1660-04-4 ]
C₂₂H₂₄N₂O₂ [ No CAS ]
C₂₂H₂₄N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%; 31%		A mixture of 10b (210 mg, 1.180 mmol) , 2-hydroxyisoindoline-1, 3-dione (38 mg, 0.233 mmol) , Bis (acetylacetonato) cobalt (30 mg, 0.117 mmol) in HOAc (5 mL) was stirred under oxygen atmosphere at 75 for 6 h. The reaction mixture was concentrated to dryness under reduced pressure. The residue was diluted with EtOAc (10 mL) and the insoluble solid was filtered off. The filtrate was concentrated in vacuo to afford a crude mixture of 14b and 14c (160 mg) as slight brown oil, which was used for the next step without further purification. To a stirred mixture of compound 10a (150 mg, 0.362 mmol) and compounds 14b and 14c (70 mg, 0.362 mmol) in anhydrous THF (10mL) was added dropwise a solution of EtONa (21in EtOH, 152mg, 0.471mmol) at room temperature. The reaction mixture was stirred at room temperature for 1.5 h. After the mixture was concentrated to dryness under reduced pressure, the residue was diluted with NH4Cl solution (10mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (8 mL) . To this solution was added HOAc (2 mL) , and the reaction mixture was stirred at 60 for 2 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (EtOAc) to afford compound 14d (70 mg, 55yield) , MS 349.2 [M+H]+, and 14e (40 mg, 31yield) as a light yellow solid, MS Found 365.2 [M+H]+.

Reference： [1]Patent: WO2016/165613,2016,A1 .Location in patent: Paragraph 136-137

11
[ 1402838-08-7 ]
[ 144783-46-0 ]
C₂₂H₂₀N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a stirred mixture of compound 11b (0.18 g, 0.73 mmol) and compound K1-3 (0.30 g, 0.73 mmol) in anhydrous THF (15 mL) was added dropwise a solution of EtONa (21in EtOH, 0.31 g, 0.94 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h, and concentrated to dryness under reduced pressure. The residue was diluted with NH4Cl solution (5 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL x 2) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (15 mL) . To this solution was added HOAc (3 mL) , and the reaction mixture was stirred at 90 for 3 h. The mixture was concentrated in vacuo to give a residue, which was diluted with saturated NaHCO3solution (10 mL) and extracted with EtOAc (10 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (CH2Cl2: MeOH 20 : 1) to afford compound 11c (0.15 g, 52yield) as a yellow solid. MS 405.2 [M+H]+.

Reference： [1]Patent: WO2016/165613,2016,A1 .Location in patent: Paragraph 126

12
[ 1402838-08-7 ]
[ 99-90-1 ]
C₁₈H₁₃BrN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a stirred mixture of compound 10a (500 mg, 1.21 mmol) and compound 1- (4-bromophenyl) ethanone (240 mg, 1.21 mmol) in anhydrous THF (20 mL) was added dropwise a solution of EtONa (21in EtOH, 508 mg, 1.57 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 h, and concentrated to dryness under reduced pressure. The residue was diluted with NH4Cl solution (20 mL) and extracted with EtOAc (20 mL x 3) . The combined organic layers were washed with brine (20 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was dissolved in MeOH (16 mL) . To this solution was added HOAc (4 mL) , and the reaction mixture was stirred at 90 for 3 h. The mixture was concentrated in vacuo to give a residue, which was diluted with NaHCO3saturated solution (20 mL) and extracted with EtOAc (20 mL x 3) . The combined organic layers were washed with brine (20 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (CH2Cl2: MeOH 50 : 1) to afford compound 12b (220 mg, 52yield) as a yellow solid. MS 353.1 [M+H]+, 355.1 [M+H]+.

Reference： [1]Patent: WO2016/165613,2016,A1 .Location in patent: Paragraph 128

13
[ 1402838-08-7 ]
[ 87661-20-9 ]
C₃₇H₃₆N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%		To a solution of 13a (52 mg, 0.363 mmol) in anhydrous THF (5 mL) was added LDA (2 M in THF, 0.2 mL, 0.40 mmol) dropwise at -78 under nitrogen. The reaction mixture was stirred at -78 for 1 h, a solution of 10a (100 mg, 0.242 mmol) in anhydrous THF (1 mL) was added dropwise. The resulting reaction mixture was warmed slowly to room temperature, and stirred for another 3 h. The reaction mixture was quenched with water and extracted with EtOAc (5 mL x 3) . The combined organic layers were washed with brine (10 mL) , dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a residue, which was purified by preparative TLC (petroleum ether : EtOAc 4 : 1) to afford compound 13b (70 mg, 52yield) as a white solid.1H NMR (CD3OD, 400 MHz) : delta 7.62-7.55 (m, 3H) , 7.45-7.36 (m, 9H) , 7.32-7.20 (m, 8H) , 7.15 (s, 1H) , 5.65 (s, 1H) , 1.15 (s, 9H) , 1.01-0.87 (m, 3H) , 0.54-0.47 (m, 1H) MS 557.3 [M+H]+.

Reference： [1]Patent: WO2016/165613,2016,A1 .Location in patent: Paragraph 131

14
[ 1402838-08-7 ]
1-acetyl-1-deuterocyclohexane [ No CAS ]
1-(1-deuterocyclohexyl)-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%		To a three-necked flask was added 2- (1-trityl-1H-imidazole-4-) benzaldehyde (400 mg, 0.97 mmol)Acetyl-1-deuterated cyclohexane (122 mg, 0.97 mmol)And anhydrous tetrahydrofuran (5 ml)Under nitrogen protection,A solution of sodium ethoxide (85 mg, 1.25 mmol) in ethanol was added at room temperature,Stir at room temperature for 3 h, spin dry solvent,Saturated ammonium chloride (10 ml) was added, Extracted with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate, the solvent was dried,Acetic acid (1 ml) and ethanol (5 ml) were added,Was stirred at 90 3h, cooled to room temperature,The organic layer was combined and dried over anhydrous sodium sulfate. The solvent was concentrated and purified by column chromatography on silica gel to give compound 23 (210 mg, yield: 77%), and the residue was extracted with ethyl acetate.

Reference： [1]Patent: CN106256830,2016,A .Location in patent: Paragraph 0103; 0107; 0108; 0109

15
[ 1402838-08-7 ]
[ 823-76-7 ]
[ 1402838-89-4 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a three-necked flask was added 2- (1-trityl-1H-imidazole-4-) benzaldehyde (400 mg, 0.97 mmol)Acetylcyclohexane (122 mg, 0.97 mmol)And anhydrous tetrahydrofuran (5 ml)Under nitrogen protection,A solution of sodium ethoxide (85 mg, 1.25 mmol) in ethanol was added at room temperature,Stir at room temperature for 3 h, spin dry solvent,Saturated ammonium chloride (10 ml) was added,The organic layer was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was dried, acetic acid (1 ml) and ethanol (5 ml) were added, stirred at 90 C for 3 h, cooled to room temperature, and saturated sodium carbonate was added to adjust pH = 10 , Extracted with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate,Concentrated solvent,Purification by column chromatography on silica gel afforded compound 9 (210 mg, yield 77%

Reference： [1]Patent: CN106256830,2016,A .Location in patent: Paragraph 0045; 0061; 0062; 0063
[2]Tetrahedron,2018,vol. 74,p. 3045 - 3051

16
[ 40138-16-7 ]
[ 87941-55-7 ]
[ 1402838-08-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In water; N,N-dimethyl-formamide; at 90℃; for 16h;Inert atmosphere;	To a single-necked flask was added <strong>[87941-55-7]4-bromo-1-trityl-1H-imidazole</strong> (1.5 g, 3.9 mmol)Sodium carbonate (1.2 g, 11.7 mmol),2-formylbenzeneboronic acid (864 mg, 5.8 mmol) and DMF (10 ml)Water (2 ml), the reaction system was filled with nitrogen,Tetrakis (triphenylphosphine) palladium (242 mg, 0.195 mmol) was added under nitrogen,90 C for 16 h, add water,Ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate, the solvent was concentrated,Purification by column chromatography on silica gel afforded compound 8 (930 mg, yield 58%).

Reference： [1]Patent: CN106256830,2016,A .Location in patent: Paragraph 0045; 0058; 0059; 0060

17
[ 1402838-08-7 ]
[ 135311-97-6 ]
7-([2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]methylidene)-5,6,7,8-tetrahydroisoquinolin-8-one [ No CAS ]

Reference： [1]Patent: WO2017/107979,2017,A1 .Location in patent: Paragraph 266

18
[ 1402838-08-7 ]
[ 90401-84-6 ]
6-(5H-imidazo[5,1-a]isoindol-5-yl)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2017/107979,2017,A1 .Location in patent: Paragraph 982

19
[ 1402838-08-7 ]
5,6,7,8-tetrahydro-4H-pyrazolo[1,5-a]azepin-4-one [ No CAS ]
(E)-5-(2-(1-trityl-1H-imidazol-4-yl)benzylidene)-5,6,7,8-tetrahydropyrazolo[1,5-a]azepin-4-one [ No CAS ]

Reference： [1]Patent: WO2017/107979,2017,A1 .Location in patent: Paragraph 2053

20
[ 1402838-08-7 ]
[ 403-42-9 ]
C₃₇H₂₇FN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
671 mg	In tetrahydrofuran; ethanol; at 10 - 35℃;	A solution of compound 5-d (166 mg, 1.2 mmol), ethanol in ethanol (20%, 0.6 mL, 1.55 mmol) was added to a solution ofTo a solution of compound 5-e (see patent: WO2012142237 method) (500 mg, 1.2 mmol) in tetrahydrofuran (6 mL)in. The reaction mixture was stirred overnight at room temperature and saturated aqueous ammonium chloride (5 mL) was added. The reaction mixture was washed with acetic acidEthyl ester (2 x 20 mL). The organic phases were combined, washed with saturated brine (10 mL), dried over anhydrous sodium sulfate, concentrated under reduced pressure,Compound 5-c (671 mg) was used directly in the next step.

Reference： [1]Patent: CN106478634,2017,A .Location in patent: Paragraph 0204; 0205; 0206

21
[ 1402838-08-7 ]
[ 90965-02-9 ]
C₃₉H₃₆N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In ethanol; for 1h;Reflux;	The compound 5-e (540 mg, 1.30 mmol), compound 29-e (see Patent: WO2012142237)(400 mg, 1.37 mmol), potassium carbonate (360 mg, 2.60 mmol) and ethanol (20 mL) was refluxed for 1 hour. Will reverseThe mixture was concentrated under reduced pressure, dichloromethane (50 mL) was added, washed successively with water (20 mL x 3) and saturated brine (50 mL).The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized from petroleum ether and ethyl acetate to giveCompound 29-d (590 mg, 78%) as a white solid.

Reference： [1]Patent: CN106478634,2017,A .Location in patent: Paragraph 0317; 0318; 0319; 0320

22
[ 1402838-08-7 ]
[ 1530-45-6 ]
ethyl 3-(2-(1-trityl-1H-imidazole-4-yl)phenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.5%		To a suspension of NaOH (0.6 g, 15.4 mmol) inwater (1 mL) at 0 C was added 7 (3.3 g, 7.7 mmol) as a solution indichloromethane (10 mL) and the mixture was stirred for 40 min.The intermediate 6 (3.2 g, 7.7 mmol) was added as a solution indichloromethane (10 mL) drop wise over a period of 3 min. Thereaction was allowed to room temperature and stirred overnight.The mixture was diluted with water and was extracted withdichloromethane to afford the crude product which was purified byflash column chromatography on silica gel to yield 8 as a faintyellow solid (2.9 g, 77.5%). Mp 110e112 C. 1H NMR (300 MHz,Chloroform-d) d(ppm) 8.17 (d, J 15.9 Hz, 1H), 7.77 (dd, J 7.8,1.4 Hz, 1H), 7.61e7.51 (m, 3H), 7.45e7.33 (m, 14H), 7.21 (td, J 7.2,6.6, 4.1 Hz, 8H), 7.06e6.89 (m, 2H), 6.32 (d, J 15.9 Hz, 1H), 4.23 (q,J 7.1 Hz, 2H), 4.07 (q, J 7.1 Hz, 1H), 1.29e1.24 (m, 3H), 1.15 (t,J 7.1 Hz, 1H). MS (EI) m/z 485.3 [MH].

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 140,p. 293 - 304

23
[ 1402838-08-7 ]
[ 823-76-7 ]
1-cyclohexyl-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium; at 0 - 20℃; for 3h;	General procedure: Different substituted ethan-1-one (1 mol equiv.) was added to asolution of NaOEt (attained from Na (2 mol equiv.) dissolved inEtOH (1.4 M) at 0 C), followed by the addition of intermediate 6(1 mol equiv.). The yellow liquid was stirred at room temperaturefor 3 h. The solvent was removed under reduced pressure and thesaturated NH4Cl solution was added to the mixture to quench thereaction. The mixture was diluted with water, and was extractedwith dichloromethane to afford the crude product, which was usedto the next step without any further purification.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 140,p. 293 - 304

24
[ 1402838-08-7 ]
[ 99-91-2 ]
C₃₇H₂₇ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; sodium; at 0 - 20℃; for 3h;	General procedure: Different substituted ethan-1-one (1 mol equiv.) was added to asolution of NaOEt (attained from Na (2 mol equiv.) dissolved inEtOH (1.4 M) at 0 C), followed by the addition of intermediate 6(1 mol equiv.). The yellow liquid was stirred at room temperaturefor 3 h. The solvent was removed under reduced pressure and thesaturated NH4Cl solution was added to the mixture to quench thereaction. The mixture was diluted with water, and was extractedwith dichloromethane to afford the crude product, which was usedto the next step without any further purification.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 140,p. 293 - 304

25
[ 1402838-08-7 ]
[ 1530-45-6 ]
ethyl (E)-3-(2-(1-triphenylmethyl-1H-imidazol-4-yl)phenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77.5%		5 (3.3 g, 7.7 mmol) was dissolved in dichloromethane (10 mL)Aqueous NaOH (0.6 g, 15.4 mmol) (1 mL) was added at 0 C,Stir at room temperature for 40 minutes.2- (1-Trityl- 1 H-imidazole) benzaldehyde (3.2 g, 7.7 mmol) was dissolved in dichloromethane (1 mL)0 C slowly dripped into the above system,After stirring for 12 hours at room temperature,Water (50 mL) was added,Dichloromethane extraction,Dried over anhydrous magnesium sulfate,Purification by column chromatography gave a pale yellow solid,Yield 77.5%.

Reference： [1]Patent: CN107501272,2017,A .Location in patent: Paragraph 0085; 0086; 0095; 0096

26
[ 1402838-08-7 ]
[ 823-76-7 ]
(E)-1-cyclohexyl-3-(2-(1-triphenylmethyl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium; In ethanol; at 20℃; for 3h;	At 0 C,Na (0.6 g, 23.9 mmol) was slowly added to ethanol (15 mL) to make a sodium ethoxide solution,Methylcyclohexyl ketone (1.5 g, 11.9 mmol) was added,4 (5.0 g, 11.9 mmol).Reaction at room temperature for 3 hours,Saturated ammonium chloride solution was added to remove the reaction,The solvent was removed under reduced pressure,Add water 15mL,Dichloromethane extraction,Dried over anhydrous magnesium sulfate,The solvent was removed under reduced pressure to give the crude product as a white solid.

Reference： [1]Patent: CN107501272,2017,A .Location in patent: Paragraph 0179; 0180; 0181; 0182

27
[ 1402838-08-7 ]
[ 25303-66-6 ]
C₃₆H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With sodium ethanolate; In tetrahydrofuran; ethanol; at 20℃;	Compound 2 (600 mg, 1.4mmol), [0056] Compound 3 (154 mg, 1.4mmol) and sodium ethoxide dissolved into THF/E0H = 6mL/2 ml, after stirring at room temperature overnight, the reaction solution is quenched with saturated ammonium chloride solution (50mL), extract with ethyl acetate (50mL chi2), wash with saturated brine (30mL), dry over anhydrous sodium sulfate, filter, spin dry under reduced pressure. The crude product is beaten with PE/EA = (5/1), filtered, dried, and obtained product compound 4 (460 mg, yield 64%).

Reference： [1]Patent: CN107556315,2018,A .Location in patent: Paragraph 0054-0056

28
[ 1402838-08-7 ]
dimethyl (2-(6-methylbenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.4%	With bismuth carbonate; In isopropyl alcohol; at 20℃; for 16h;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (266 mg, 0.644 mmol, 1 eq),Compound (dimethyl 2-(6-methylbenzofuran-5-yl)-2-oxoethyl)phosphonate (0207-25) (200 mg, 0.709 mmol, 1.1 eq) andBismuth carbonate (460 mg, 1.418 mmol, 2 equivalents)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product 1-(6-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl) Phenyl)prop-2-en-1-one (310 mg, yield: 84.4%) was a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0180

29
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(6-(trifluoromethyl)benzofuran-5-yl)ethyl)phosphonate [ No CAS ]
1-(6-(trifluoromethyl)benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
176 mg	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	The compound (2-oxo-2-(6-trifluoromethylbenzofuran-5-yl)ethyl) dimethyl phosphate (0207-30) (262 mg, 0.78 mmol, 1.2 eq.)<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (270 mg, 0.65 mmol, 1.0 equiv) andCesium carbonate (847 mg, 2.6 mmol, 4.0 eq.)Mixed in isopropyl alcohol (20 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a residue which was purified by column chromatography (petroleum ether/ethyl acetate=5/1 to 1/1). The target product (176 mg, yield: 43.3%) was obtained as a yellow gum.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0188

30
[ 1402838-08-7 ]
dimethyl(2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
(Z)-1-(2,3-dihydrobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (500 mg, 1.2 mmol, 1.0 equiv),Compound (2-(2,3-dihydrobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0402-36) (420 mg, 1.5 mmol, 1.3 equivalents) andCesium carbonate (782 mg, 2.4 mmol, 2.0 equiv)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is over, quench with water,The mixture was extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol = 100/1 to 50/1) to give the product.(Z)-1-(2,3-dihydrobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propane-2- Alken-1-one (500 mg, Yield: 74%)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0212

31
[ 1402838-08-7 ]
dimethyl (2-(6-fluoro-2,3-dihydrobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-fluoro-2,3-dihydrobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	<strong>[1402838-08-7]2-(1-triphenylmethyl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (263 mg, 0.635 mmol, 1 eq),Compound (2-(6-Fluoro-2,3-dihydrobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0403-42) (377 mg, 1.3 mmol, 1.3 eq. )And cesium carbonate (412 mg, 1.27 mmol, 2 eq.)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product 1-(6-fluoro-2,3-dihydrobenzofuran-5-yl)-3-(2-(1-triphenylmethyl-1H-) Imidazol-5-yl)phenyl)prop-2-en-1-one (280 mg, crude) was a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0218

32
[ 1402838-08-7 ]
dimethyl (2-(furo[2,3-b]pyridin-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(furo[2,3-b]pyridin-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22 mg		In the atmosphere of nitrogen and ice bath conditions,Will be 60% sodium hydride (9.5 mg, 0.394 mmol, 2.0 equiv)Dissolved in 10 ml of tetrahydrofuran.The dimethyl 2-(furo[2,3-b]pyridin-5-yl)-2-oxoethyl)phosphate (0207-49) (53 mg, 0.197 mmol, 1.0 eq) was slowly addedTetrahydrofuran solution (10 ml).After stirring the mixture for 15 minutes,<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (82 mg, 0.197 mmol, 1.0 equiv)A solution of tetrahydrofuran (10 ml) was added dropwise.The mixture was stirred at ice bath for 0.5 hours.The reaction was warmed to room temperature and stirred overnight.After completion of the reaction, the mixture was quenched with a saturated aqueous solution of ammonium chloride and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a yellow oil.The resulting yellow oil was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether = 1/2) to give the desired product.1-(Furano[2,3-b]pyridin-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-ene-1 -ketone (22 mg, yield: 20%) is a yellow oil

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0225

33
[ 1402838-08-7 ]
tert-butyl ((5-(2-(dimethoxyphosphoryl)acetyl)-1-benzofuran-2-yl)methyl) carbonate [ No CAS ]
tert-butyl ((5-(3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)acryloyl)benzofuran-2-yl)methyl)carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.14%	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	2-(1-trityl-1H-imidazol-5-yl)benzaldehyde (0105-1) (200 mg, 0.483 mmol, 1 eq),Compound ((5-(2-(dimethoxyphosphoryl)acetyl)benzofuran-2-yl)methyl) tert-butyl carbonate (0207-50) (211 mg, 0.531 mmol, 1.1 eq.) withCesium carbonate (314 mg, 0.966 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and filtered to give the target product (305 mg, yield: 92.14%) as a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0232

34
[ 1402838-08-7 ]
dimethyl (2-(2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
273 mg	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	The compound (2-(2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl) dimethyl phosphate (0207-59) (391 mg, 1.2 mmole , 2.0 eq),Compound <strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (250 mg, 0.6 mmol, 1.0 equiv) andCesium carbonate (489 mg, 1.5 mmol, 2.5 eq.)Mixed in isopropyl alcohol (30 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a residue. Purification by column chromatography (eluent: petroleum ether/ethyl acetate = 5/1) ~1/1) Target product 1-(2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazole-4) -yl)phenyl)prop-2-en-1-one (273 mg, yield: 74%) as a yellow gum

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0238

35
[ 1402838-08-7 ]
dimethyl (2-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-5-yl)-2-oxoethyl)phosphate (0207-60) (400 mg, 1.47 mmol, 3.3 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (180 mg, 0.44 mmol, 1.0 equiv) andCesium carbonate (958 mg, 2.94 mmol, 2.0 eq.)Added to 40 ml of isopropanol,Stir the reaction overnight at room temperature,Concentrate under reduced pressure, add ethyl acetate and water, separate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 1-(6-fluoro-2-(2-hydroxypropan-2-yl)benzofuran-) as a yellow solid. 5-base)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (540 mg, crude)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0244

36
[ 1402838-08-7 ]
dimethyl (2-(2-methylbenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(2-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃; for 8h;	Dimethyl (2-(2-methylbenzofuran-5-yl)-2-oxoethyl)phosphate (0304-68) (226 mg, 0.80 mmol, 1.1 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (300 mg, 0.73 mmol, 1.0 equiv) andCesium carbonate (473 mg, 1.45 mmol, 2.0 eq.)Added to 40 ml of isopropanol,The reaction is stirred at room temperature for 8 hours,Concentrate under reduced pressure, add ethyl acetate and water,The solution was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the product 1-(2-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazole-) as a yellow solid. 4-yl)phenyl)prop-2-en-1-one (500 mg, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0252

37
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(2-phenylbenzofuran-5-yl)ethyl)phosphonate [ No CAS ]
1-(2-phenylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.7%	With caesium carbonate; In isopropyl alcohol; at 20℃;	Will (2-(2-phenylbenzofuran-5-yl)-2-oxoEthyl) dimethyl phosphate (0207-79) (254 mg, 0.738 mmol, 1.0 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (305 mg, 0.738 mmol, 1.0 equiv) andCesium carbonate (480 mg, 1.476 mmol, 2.0 equiv)The isopropanol solution (10 ml) was stirred overnight at room temperature.After the reaction is completed, quench with water, dichlorineMethane extraction, the organic phase is washed with saturated brine,It was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow oil.The resulting yellow oil was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether = 1/2) to give the target product 1-(2-phenylbenzene)(Furan-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propan-2-en-1-one (306 mg, Yield:65.7%) is a yellow oil.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0258

38
[ 1402838-08-7 ]
dimethyl (2-(6-fluoro-2-phenylbenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-fluoro-2-phenylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (287 mg, 0.693 mmol, 1 eq),Compound (2-(6-fluoro-2-phenylbenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-80) (300 mg, 0.83 mmol, 1.2 equiv) andCesium carbonate (450 mg, 1.386 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product 1-(6-fluoro-2-phenylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one (250 mg, crude) is a yellow solid

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0264

39
[ 1402838-08-7 ]
dimethyl (2-(3-methylbenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(3-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In isopropyl alcohol; at 20℃; for 8h;	Dimethyl (2-(3-methylbenzofuran-5-yl)-2-oxoethyl)phosphate (1007-95) (400 mg, crude),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (300 mg, 0.73 mmol, 1.0 equiv) andCesium carbonate (473 mg, 1.45 mmol, 2.0 eq.)Added to 40 ml of isopropanol,The reaction is stirred at room temperature for 8 hours,Add 1g of benzaldehyde to remove the remaining phosphorous reagent.Concentrate under reduced pressure, add ethyl acetate and water, separate, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a yellow liquid.1-(3-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one ( 2.0 grams, crude product).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0274

40
[ 1402838-08-7 ]
dimethyl (2-(dibenzo[b,d]furan-2-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(dibenzo[b,d]furan-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (200 mg, 0.483 mmol, 1.0 equiv),Compound (2-(Diphenyl[b,d]furan-2-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0604-96) (170 mg, 0.53 mmol, 1.1 eq) andCesium carbonate (315 mg, 0.966 mmol, 2.0 equiv)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight. After the reaction is over, add water andSolids precipitated, filtered and the cake was dried to give the product 1-(diphenyl[b,d]furan-2-yl)-3-(2-(1-trityl-1H-)Imidazol-4-yl)phenyl)prop-2-en-1-one (300 mg, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0281

41
[ 867-13-0 ]
[ 1402838-08-7 ]
ethyl (Z)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (480 mg, 1.2 mmol, 1.0 equiv),Triethyl phosphonoacetate (528 mg, 2.4 mmol, 2.0 equiv) andCesium carbonate (786 mg, 2.4 mmol, 2.0 equiv)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is completed, quench with water, extract with dichloromethane, dry the organic phase over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain the product (Z)-3-(2-(1-trityl-1H-imidazole-4) - yl) phenyl) ethyl acrylate (600 mg, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0285

42
[ 1402838-08-7 ]
dimethyl (2-(benzofuran-6-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(benzofuran-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(benzofuran-6-yl)-2-oxoethyl)phosphate (0304-101) (161 mg, 0.6 mmol, 1.0 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (250 mg, 0.6 mmol, 1.0 equiv) andCesium carbonate (392 mg, 1.2 mmol, 2.0 equiv)Added to 40 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was separated and dried over anhydrous sodium sulfate.Shrink to give a slightly yellow solid of 1-(benzofuran-6-yl)-2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (370 Milligrams, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0296

43
[ 1402838-08-7 ]
dimethyl (2-(3-fluoro-4-nitrophenyl)-2-oxoethyl)phosphonate [ No CAS ]
(Z)-1-(3-fluoro-4-nitrophenyl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (1.4 g, 3.37 mmol, 1.0 equiv),Compound (2-(3-Fluoro-4-nitrophenyl)-2-oxoethyl)phosphoric acid dimethyl ester (0702-102) (1.36 g, 4.38 mmol, 1.3 equivalents) andCesium carbonate (2.2 g, 6.74 mmol, 2.0 eq.)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction was completed, quenched with water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=100/1-50/ 1) Purification,The product (Z)-1-(3-fluoro-4-nitrophenyl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-ene is obtained 1-ketone (1.8 g, yield: 92%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0301

44
[ 1402838-08-7 ]
methyl 6-fluoro-2-methylbenzofuran-5-carboxylate [ No CAS ]
[ 756-79-6 ]
1-(6-fluoro-2-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41.9%		In the atmosphere of nitrogen,Dimethyl methylphosphonate (402 mg, 3.24 mmol, 1.5 equiv)Dissolved in 5 ml of dry tetrahydrofuran.Cool to -60C with dry ice/ethanol.n-Butyllithium (1.70 ml, 2.5 mol/ml n-hexane solution, 4.32 mmol, 2 eq.) was slowly added dropwise.The mixture is stirred at this temperature for 30 minutes.The compound 6-fluoro-2-methylbenzofuran-5-carboxylic acid methyl ester (0303-69) (450 mg, 2.16 mmol, 1 eq.) was slowly added dropwise.A solution of tetrahydrofuran (5 ml).The mixture was stirred at this condition for 1 hour. Isopropanol (15 ml), cesium carbonate (1.0 g, 3.24 mmol, 1.5 eq) and 2-(1-Tri) were addedBenzyl-1H-imidazol-4-yl)benzaldehyde (0105-1) (894 mg, 2.16 mmol, 1 eq.) stirred at room temperatureAfter 16 hours, after the reaction was completed, water (50 ml) was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated brine and anhydrous sulfuric acid.The sodium was dried, concentrated under reduced pressure, and purified by silica gel column chromatography to give the product 1-(6-fluoro-2-methylbenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (530 mg, yield 41.9%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0469

45
[ 1402838-08-7 ]
tert-butyl 5-(2-(dimethoxyphosphoryl)acetyl)-1H-indazole-1-carboxylate [ No CAS ]
tert-butyl 5-(3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)acryloyl)-1H-indazole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	5-(2-(Dimethoxyphosphoryl)acetyl)-1H-carbazole-1-carboxylic acid tert-butyl ester (0304-105) (375 mg, 1.0 mmol, 1.4 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (300 mg, 0.73 mmol, 1.0 equiv) andCesium carbonate (900 mg, 2.8 mmol, 3.8 eq.)Added to 60 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added,The layers were separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the product as a yellow solid 5-(3-(2-(1-triphenylmethyl-1H-imidazole-4-(phenyl)acryloyl)-1H-carbazole-1-carboxyl

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0321

46
[ 1402838-08-7 ]
dimethyl (2-(benzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
(Z)-1-(benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.7%		In the atmosphere of nitrogen and ice bath conditions,Will be 60% sodium hydride (34 mg, 0.844 mmol, 1.0 equiv)Dissolved in 15 ml of tetrahydrofuran.Dimethyl (2-(benzofuran-5-yl)-2-oxoethyl)phosphonate (0207-1) (226 mg, 0.844 mmol, 1.0 equiv) was slowly addedTetrahydrofuran solution (15 ml).After stirring the mixture for 15 minutes,<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (350 mg, 0.844 mmol, 1.0 equiv) was added dropwiseA solution of tetrahydrofuran (20 ml).The mixture was stirred at ice bath for 0.5 hours.The reaction was warmed to room temperature and stirred overnight.After completion of the reaction, the mixture was quenched with a saturated aqueous solution of ammonium chloride and extracted with dichloromethane. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a yellow oil. The resulting yellow oil was purified by column chromatography on silica gel (eluent: ethyl acetate/petroleum ether = 1/2) to give a yellow oil (Z)-1-(Benzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (356 Mg, yield: 75.7%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0119

47
[ 1402838-08-7 ]
dimethyl (2-(benzo[d]isoxazol-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(benzo[d]isoxazol-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(benzo[d]isoxazol-5-yl)-2-oxoethyl)phosphate (0304-108) (0.97 mmol, 1.2 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (389 mg, 0.94 mmol, 1.0 equiv) andCesium carbonate (612 mg, 1.88 mmol, 2.0 eq.)Added to 30 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was anhydrous.Drying over Na2SO4 and concentration under reduced pressure gives the product as a yellowish solid. 1-(Benzo[d]isoxazol-5-yl)-3-(2-(1-triazine)-lH-imidazol-4-yl)phenyl)prop-2-en-1-one (600 mg, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0335

48
[ 1402838-08-7 ]
[ 116679-39-1 ]
1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
413 mg	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	Compound 0403-119 (397 mg, 1.39 mmol, 1.9 equiv),Compound <strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (300 mg, 0.72 mmol, 1 eq) andCesium carbonate (468 mg, 1.44 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and filtered to give the target product 1-(benzodioxan-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)benzene. The base) propane-2-en-1-one (413 mg, yield: 99.27%) was a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0347

49
[ 1402838-08-7 ]
[ 51638-46-1 ]
(E)-1-(naphthalen-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81.64%	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (474 mg, 1.15 mmol, 1 eq),Compound (2-(Nethyl-2-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0803-123) (350 mg, 1.26 mmol, 1.1 eq.)And cesium carbonate (407 mg, 1.15 mmol, 2 eq.)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product(E)-1-(Nethyl-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (538 mg , Yield: 81.64%) as a white solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0353

50
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(quinolin-6-yl)ethyl)phosphonate [ No CAS ]
1-(quinolin-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-oxo-2-(quinolin-6-yl)ethyl) phosphate (0803-125) (267 mg, 0.96 mmol, 1.1 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (360 mg, 0.87 mmol, 1.0 equiv) andCesium carbonate (706 mg, 2.17 mmol, 2.5 eq.)Added to 60 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was separated and dried over anhydrous sodium sulfate and concentrated under reduced pressure.Purification by column chromatography on silica gel (eluent: petroleum ether: ethyl acetate = 5: 1) gave the product 1-(quinolin-6-yl)-3-(2-(1-trityl)methyl as a yellow solid. -lH-imidazol-4-yl)phenyl)prop-2-en-1-one (490 mg, yield: 99%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0359

51
[ 1402838-08-7 ]
C₁₃H₁₄NO₄P [ No CAS ]
1-(isoquinolin-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
300 mg	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (250 mg, 0.6 mmol, 1.0 equiv),Compound (dimethyl 2-(isoquinolin-6-yl)-2-oxoethyl)phosphate (0803-127) (400 mg, 1.4 mmol, 2.3 eq.)And cesium carbonate (391 mg, 1.2 mmol, 2.0 equiv)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is completed, quench with water, extraction with dichloromethane, anhydrous sulfur in the organic phaseThe sodium sulfate was dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=100/1-50/1) to give a product.1-(isoquinolin-6-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (300 mg, Rate: 87%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0365; 0370

52
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(quinolin-3-yl)ethyl)phosphonate [ No CAS ]
1-(quinolin-3-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
220 mg	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (250 mg, 0.6 mmol, 1.0 equiv),Compound (2-(quinolin-3-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0803-131) (420 mg, 1.5 mmol, 2.5 equiv) andCesium carbonate (698 mg, 2.14 mmol, 3.6 eq.)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is completed, quench with water, extract with dichloromethane, and dry the organic phase with anhydrous sodium sulfate.Dry, concentrate under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=100/1-50/1) to give the product as a yellow solid compound 1-(quinolin-3-yl)- 3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (220 mg, yield: 64.5%)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0379

53
[ 1402838-08-7 ]
dimethyl (2-(isoquinolin-3-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(isoquinolin-3-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
200 mg	With caesium carbonate; In isopropyl alcohol; at 20℃;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (250 mg, 0.6 mmol, 1.0 equiv),Compound (dimethyl 2-(isoquinolin-3-yl)-2-oxoethyl)phosphonate (0803-132) (350 mg, 1.25 mmol, 2.2 equiv) andCesium carbonate (391 mg, 1.2 mmol, 2.0 eq.) In isopropanol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is completed, pour into 100 ml of water and filter the resulting solid as a product1-(isoquinolin-3-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (200 mg,Rate: 58.7%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0385

54
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(quinolin-2-yl)ethyl)phosphonate [ No CAS ]
1-(quinolin-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(quinolin-2-yl)-2-oxoethyl)phosphate (0803-133) (279 mg, 1.0 mmol, 1.0 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (414 mg, 1.0 mmol, 1.0 equiv) andCesium carbonate (651 mg, 2.0 mmol, 2.0 equiv)The isopropanol solution (10 ml) was stirred overnight at room temperature.After the reaction is completed, quench with water, extract with dichloromethane, and wash the organic phase with saturated saline solution.Dry and concentrate under reduced pressure to give a yellow oil. The resulting yellow oil was passed through silica gel column chromatography (eluent: dichloromethane/methylPurification with alcohol = 100/1 to 100/5) yields the target product 1-(quinolin-2-yl)-3-(2-(1-trityl-1H-imidazole-4-)Phenyl)propan-2-en-1-one (200 mg, crude) is a yellow oil

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0391

55
[ 1402838-08-7 ]
dimethyl (2-oxo-2-(quinoxalin-2-yl)ethyl)phosphonate [ No CAS ]
1-(quinoxalin-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(quinoxalin-2-yl)-2-oxoethyl)phosphate (0803-134) (224 mg, 0.80 mmol, 1.1 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (300 mg, 0.73 mmol, 1.0 equiv) andCesium carbonate (472 mg, 1.45 mmol, 2.0 eq.)Added to 40 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was separated and dried over anhydrous sodium sulfate.Shrink to give yellow solid product 1-(quinoxalin-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propan-2-ene-1- Ketone (400 mg, crude product)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0397

56
[ 1402838-08-7 ]
dimethyl (2-(benzofuran-2-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(benzofuran-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) 200 mg, 0.48 mmol, 1.0 eq),Compound (dimethyl 2-(benzofuran-2-yl)-2-oxoethyl)phosphate (0903-135) (257 mg, 0.96 mmol, 2.0 equiv) andCesium carbonate (313 mg, 0.96 mmol, 2.0 eq.)Mixed in isopropyl alcohol (30 ml),The reaction was stirred at room temperature overnight.After the reaction is completed, quench with water, precipitate solids, filter, and dry.Obtained compound 1-(benzofuran-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (290 mg ,Crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0403

57
[ 1402838-08-7 ]
dimethyl (2-(benzo[b]thiophen-2-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(benzo[b]thiophen-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(benzothiophen-2-yl)-2-oxoethyl)phosphate (0903-137) (284 mg, 1.0 mmol, 1.0 eq),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (414 mg, 1.0 mmol, 1.0 equiv) andCesium carbonate (651 mg, 2.0 mmol, 2.0 equiv)The isopropanol solution (10 ml) was stirred overnight at room temperature.After completion of the reaction, quench with water, extract with dichloromethane, wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to give a yellow oil. The resulting yellow oil was subjected to silica gel column chromatography (eluent: acetic acid). Ethyl ester/petroleum ether = 1/2) purification,The target product 1-(benzothiophen-2-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (200) was obtained. Milligram, crude) is a yellow oil.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0409

58
[ 1402838-08-7 ]
dimethyl (2-(benzo[b]thiophen-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
(E)-1-(benzo[b]thiophen-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
500 mg	With bismuth carbonate; In isopropyl alcohol; at 20℃; for 8h;	(2-(Benzo[b]thiophen-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0304-7) (267 mg, 0.97 mmol, 1.1 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1)(350 mg, 0.85 mmol, 1.0 eq) andBismuth carbonate (418 mg, 1.28 mmol, 1.5 eq.)Added to 30 ml of isopropanol,The reaction is stirred at room temperature for 8 hours,Concentrate under reduced pressure, add ethyl acetate and water, and separateDried over anhydrous sodium sulfate and concentrated under reduced pressure to give a slightly yellow solid product(E)-1-(Benzo[b]thiophen-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-ene-1 - Ketone (500 mg, Yield: 90%)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0127

59
[ 1402838-08-7 ]
dimethyl (2-(7-chloro-6-fluorobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(7-chloro-6-fluorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃;	(2-(7-chloro-6-fluorobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-19) (185 mg, 0.55 mmol, 1.0 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (228 mg, 0.55 mmol, 1.0 equiv) andCesium carbonate (359 mg, 1.1 mmol, 2.0 equiv)Added to 20 ml of isopropanol,The reaction was stirred at room temperature overnight, concentrated under reduced pressure, ethyl acetate and water were added, and the mixture was separated and dried over anhydrous sodium sulfate and concentrated under reduced pressure.The product was obtained as a yellowish solid, 1-(7-chloro-6-fluorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)propane- 2-Elen-1-one (150 mg, crude).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0458

60
[ 1402838-08-7 ]
tert-butyl (5-(2-(dimethoxyphosphoryl)acetyl)-6-fluorobenzofuran-2-yl)methyl carbonate [ No CAS ]
tert-butyl (6-fluoro-5-(3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)acryloyl)benzofuran-2-yl)methyl carbonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (696 mg, 1.68 mmol, 1 eq),Compound ((5-(2-(Dimethoxyphosphoryl)acetyl)-6-fluorobenzofuran-2-yl)methyl) tert-butyl carbonate (0207-51) (772Mg, 1.85 mmol, 1.1 eq) andCesium carbonate (1090 mg, 3.36 mmol, 2 eq)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the product ((6-Fluoro-5-(3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)acryloyl)benzene. tert-Butyl furan-2-yl)methyl)carbonate (930 mg, crude) is a yellow solid

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0464

61
[ 1402838-08-7 ]
5-acetylbenzofuran-2-carboxylic acid ethyl ester [ No CAS ]
ethyl 5-(2-(5H-imidazo[5,1-a]isoindol-5-yl)acetyl)benzofuran-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.5%	With sulfuric acid; In ethanol; at 90℃; for 18h;Cooling with ice;	5-Acetylbenzofuran-2-carboxylic acid methyl ester (0506-89) (200 mg, 0.86 mmol, 1.0 equiv) and<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (534 mg, 1.3 mmol, 1.5 eq.)Soluble in ethanol (10 ml),Concentrated sulfuric acid 5 ml was added dropwise under ice bath conditions.The temperature was raised to 90C and the reaction was stirred for 18 hours.Cool to room temperature, add dropwise to ice water, add ice bath, add sodium hydroxide to adjust the pH>8, ethyl acetate extraction,The liquid was separated, spin-dried, and the crude product was purified by silica gel column chromatography (eluent: dichloromethane/methanol=200/1 to 40/1) to give the product 5-(2-(5H-imidazole)[5,1-a Ethyl isomorpholin-5-yl)acetyl)benzofuran-2-carboxylate (95 mg, 28.5%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0475

62
[ 1402838-08-7 ]
dimethyl (2-(6-bromobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-bromobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.8%	With caesium carbonate; In isopropyl alcohol; at 20℃; for 18h;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (240 mg, 0.58 mmol, 1.0 equiv),(2-(6-Bromobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-156) (200 mg, 0.58 mmol, 1.0 equiv) andCesium carbonate (378 mg, 1.16 mmol, 2.0 eq.)Mixed in isopropanol (10 ml),The reaction was performed at room temperature for 18 hours.After quenching with water, ethyl acetate extractionTake, dried over anhydrous sodium sulfate, spin-dry to give a yellow solid product 1-(6-bromobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl) Phenyl)prop-2-en-1-one (350 mg, yield: 94.8%).

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0208-156

63
[ 1402838-08-7 ]
1-(2-chlorobenzofuran-5-yl)ethan-1-one [ No CAS ]
1-(2-chlorobenzofuran-5-yl)-2-(5H-imidazo[5,1-a]isoindol-5-yl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46.5%	With sulfuric acid; In 1,4-dioxane; at 90℃; for 18h;Cooling with ice;	1-(2-chlorobenzofuran-5-yl)ethane-1-one (0506-157) (120 g, 0.61 mmol, 1.0 equiv) and<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (380 mg, 0.92 mmol, 1.5 equiv)Dissolved in 10 ml dioxaneAdd 1 ml concentrated sulfuric acid dropwise to the ice bath.The temperature was raised to 90C and the reaction was stirred for 18 hours.Cool to room temperature and add dropwise to ice water. Under ice bath, add sodium hydroxide to adjust pH>8, extract with ethyl acetate, separate, spin dry, and purify the crude product with silica gel column chromatography (eluent: Dichloromethane/methanol = 200/1 to 40/1) gives the product1-(2-Chlorobenzofuran-5-yl)-2-(5H-imidazo[5,1-a]isoindoline-5-yl)ethane-1-one (100 mg, 46.5%) .

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0491

64
[ 1402838-08-7 ]
dimethyl (2-(6-fluorobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-fluorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.38%	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong>(0105-1) (263 mg, 0.635 mmol, 1 eq),Compound (2-(6-fluorobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-8) (200 mg, 0.699 mmol, 1.1 equiv) andCesium carbonate (619 mg, 1.905 mmol, 2 eq) was mixed in isopropanol (10 ml).The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter to obtain the target product1-(6-fluorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (304 Milligram, yield: 83.38%) is a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0136

65
[ 1402838-08-7 ]
dimethyl (2-(7-fluorobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(7-fluorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45.2%		In the atmosphere of nitrogen and ice bath conditions,Will be 60% sodium hydride (38 mg, 0.97 mmol, 1.0 equiv)Dissolved in 15 ml of tetrahydrofuran,(2-(7-Fluorobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-14) (278 mg, 0.97 mmol, 1.0 equiv) was slowly addedTetrahydrofuran solution (15 ml).After stirring the mixture for 15 minutes,<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (402 mg, 0.97 mmol, 1.0 equiv)A solution of tetrahydrofuran (20 ml) was added dropwise thereto.The mixture was stirred at ice bath for 0.5 hours.The reaction was warmed to room temperature and stirred overnight. After the reaction is completed, quench with saturated aqueous ammonium chloride, dichlorineMethane was extracted and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a yellow oil. The result isPurification by silica gel column chromatography (eluent: ethyl acetate/petroleum ether = 1/2) yields the desired product 1-(7-fluorobenzofuran-5-Radyl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (252 mg, yield: 45.2%) wasYellow oil.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0145

66
[ 1402838-08-7 ]
dimethyl (2-(6-chlorobenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-chlorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70.1%	With bismuth carbonate; In isopropyl alcohol; at 20℃; for 16h;	<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong>(0105-1) (266 mg, 0.644 mmol, 1 eq),(2-(6-chlorobenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-17) (200 mg, 0.709 mmol, 1.1 equiv) andBismuth carbonate (460 mg, 1.418 mmol, 2 equivalents)Mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction is completed, quench with water and filter.The target product 1-(6-chlorobenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)propan-2-ene-1- Ketone (290 mg, yield: 70.1%) was a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0154

67
[ 1402838-08-7 ]
dimethyl (2-(6-methoxybenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(6-methoxybenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In isopropyl alcohol; at 20℃; for 16h;	2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (0105-1) (207 mg, 0.5 mmol, 1 eq),Compound (2-(6-methoxybenzofuran-5-yl)-2-oxoethyl)phosphoric acid dimethyl ester (0207-22) (179 mg, 0.6 mmol,1.2 eq) and cesium carbonate (325 mg, 1 mmol,2 equivalents) mixed in isopropanol (10 ml),The mixture was stirred at room temperature for 16 hours.After the reaction was completed, quenched with water and filtered to give the target product 1-(6-methoxybenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-5-yl). Phenyl)prop-2-en-1-one (248 mg, crude) was a yellow solid.

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0163

68
[ 1402838-08-7 ]
dimethyl (2-(7-methoxybenzofuran-5-yl)-2-oxoethyl)phosphonate [ No CAS ]
1-(7-methoxybenzofuran-5-yl)-3-(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62.6%	With bismuth carbonate; In isopropyl alcohol; at 20℃;	Dimethyl (2-(7-methoxybenzofuran-5-yl)-2-oxoethyl)phosphate (0207-23) (317 mg, 1.1 mmol, 1.25 equiv),<strong>[1402838-08-7]2-(1-trityl-1H-imidazol-4-yl)benzaldehyde</strong> (0105-1) (331 mg, 0.8 mmol, 1.0 equiv) andBismuth carbonate (553 mg, 1.6 mmol, 2.0 equiv)Added to 40 ml of isopropanol,Stir the reaction overnight at room temperature,Concentrate under reduced pressure, add ethyl acetate and water,The liquid was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the product 1-(7-methoxybenzofuran-5-yl)-3- as a slightly yellow solid.(2-(1-trityl-1H-imidazol-4-yl)phenyl)prop-2-en-1-one (390 mg, yield: 62.6%)

Reference： [1]Patent: CN107383024,2017,A .Location in patent: Paragraph 0171

69
[ 1402838-08-7 ]
C₁₇H₂₃FNO₅P [ No CAS ]
C₄₅H₄₀FN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%		Compound 4 (196 mg, 0.51 mmol) was dissolved in 10 mL of anhydrous tetrahydrofuran, and 30.5 mg of sodium hydride was added on an ice bath, and the mixture was warmed to room temperature and stirred for 1 hour. A solution of compound 4a (211 mg, 0.51 mmol) in 5 mL of anhydrous tetrahydrofuran was added to the reaction flask in an ice bath. The mixture was warmed to room temperature, stirred overnight, quenched with saturated ammonium chloride, added with 100 mL of water and extracted with dichloromethane (50 mL×3). The combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by column chromatography to give Compound 5 (134 mg, yield 39%).

Reference： [1]Patent: CN107488179,2017,A .Location in patent: Paragraph 0311; 0312; 0319; 0320; 0321

70
[ 1402838-08-7 ]
C₂₀H₂₇FNO₅P [ No CAS ]
C₄₇H₄₂FN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%		Compound 4 (210 mg, 0.51 mmol) was dissolved in 10 mL of anhydrous tetrahydrofuran, 30.5 mg of sodium hydride was added under ice-cooling, and the mixture was warmed to room temperature and stirred for 1 hour. Compound 4a (211 mg, 0.51 mmol) was dissolved in 5 mL of anhydrous tetrahydrofuran in an ice bathAdd to the reaction flask. Warm to room temperature and stir overnight. Quench with saturated ammonium chloride. Add 100 mL water. Use dichloromethane.(50 mL x 3) extraction, and the combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. Crude product chromatographyThe product Compound 5 (128 mg, yield 36.0%) was obtained.

Reference： [1]Patent: CN107488179,2017,A .Location in patent: Paragraph 0164; 0165; 0166; 0167; 0172; 0173

71
[ 1402838-08-7 ]
[ 206989-61-9 ]
C₄₁H₄₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium ethanolate; In tetrahydrofuran; ethanol; at 0℃;	2-(1-Trityl-1H-imidazol-4-yl)benzaldehyde (4.0 g, 9.66 mmol) was dissolved in dry THF (20 mL)In a mixed solution with anhydrous EtOH (20 mL), cooled to 0 C, then EtONa (986 mg, 14.5 mmol), tert-butyl 4-acetylpiperidine-1-carboxylate (2.29 g, 10.1 mmol).Then the reaction solution was stirred at room temperature overnight, and the reaction was complete by LCMS.After that, it was diluted with ice water (30 mL), and the THF was evaporated under reduced pressure, and filtered, and the filter cake was drained as much as possible to obtain a crude white solid.(E)-4-(3-(2-(1-tritylmethyl-1H-imidazol-4-yl)phenyl)acryloyl)piperidine-1-carboxylic acid tert-butyl ester(6.0g), used directly in the next step.

Reference： [1]Patent: CN108203438,2018,A .Location in patent: Paragraph 0151; 0152; 0153; 0154

72
[ 1402838-08-7 ]
[ 76377-01-0 ]
1-(2-hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)-2-{5H-imidazo[5,1-a]isoindol-5-yl}ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		1-(2-Hydroxy-1,2,3,4-tetrahydronaphthalen-2-yl)ethyl-1-one (100 mg, 0.46 mmol),2-(1-Triphenylmethyl-1H-imidazol-4-yl)benzaldehyde (190 mg, 0.46 mmol) was dissolved in tetrahydrofuran (4.0 mL).The sodium ethoxide solution (31 mg, 21%/wt%) was added dropwise and stirred at room temperature overnight.After TLC monitoring, the reaction was completed, the solvent was evaporated under reduced pressure, and saturated ammonium chloride solution (10 mL) was added.Extracted with dichloromethane (20 mL), and the organic phase was evaporated to dryness.The residue was used directly in the next step.The residue obtained above was dissolved in a mixed solution of methanol (4 mL) and acetic acid (1 mL).After reacting at 90 C for 3 h, TLC detected the reaction completely.The solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography.Obtained the target Compound114mg,The yield was 72%.

Reference： [1]Patent: CN108424415,2018,A .Location in patent: Paragraph 0227; 0228; 0229; 0230

73
[ 1402838-08-7 ]
C₁₀H₆ClFN₆O₃ [ No CAS ]
C₃₉H₂₆ClFN₈O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; at 20℃;	step 1.312 mg of compound 22 was dissolved in 10 ml of tetrahydrofuran.Add 414 mg of compound 26,Add 2 drops of acetic acid dropwise, react at room temperature until the starting reaction is complete.Squeeze off most of the THF under reduced pressure, add water and ethyl acetate.The organic phase was separated, the organic phase was washed with saturated NaCI solution and dried over anhydrous NaSO4, Obtaining compound 32,Directly invest in the next step;

Reference： [1]Patent: CN108689958,2018,A .Location in patent: Paragraph 0151-0153

74
[ 1402838-08-7 ]
[ 103978-12-7 ]
(3-((tert-butyldimethylsilyloxy)methyl)phenyl)(2-(1-trityl-1H-imidazol-4-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%		Under nitrogen, a solution of [(3-bromophenyl)methoxy](tert-but l)dimethylsilane (7.3 g, 24.23 mmol) in THF (50 mL) was added n-BuLi (10 mL, 106.16 mmol, 2.5 M in THF) at -78 C. The resulting solution was stirred for lh at -78C. Then 2-[l -(triphenylmethyl)-lH- imidazol-4-yl]benzaldehyde (2 g, 4.83 mmol) was added, the resulting solution was allowed to react, with stirring, for an additional 5 h at room temperature. The reaction was then quenched by water (100 mL). The resulting solution was extracted with EA (3 x 100 mL) and the organic layers combined. The solution was concentrated under vacuum. The residue was purified by silica gel column eluting with EA/petroleum ether (1 :3). This resulted in 1.5 g (49%) of (3- [[(ter^bufyldimethylsilyl)oxy]methyl]phenyl)([2-[l-(triphenylmethyl)-lH-inii yl]phenyl])methanol as a yellow solid. LCMS (ESI, m/z): 638.2 [M+H]+.

Reference： [1]Patent: WO2019/6047,2019,A1 .Location in patent: Paragraph 0156; 0157; 0158

75
[ 1020743-37-6 ]
[ 1402838-08-7 ]
3-(hydroxy(2-(1-trityl-1H-imidazol-4-yl)phenyl)methyl)-N,N-bis(4-methoxybenzyl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		To a solution of 3-bromo-N,N-bis(4-methoxybenzyl)benzenesulfonamide (2.10 g, 3.55 mmol) in THF (25 niL) at - 78 C was added n-BuLi (1.54 mL, 3.38 mmol, 2.2 M solution in hexane) dropwise over a period of 5 minutes, the resulting yellow solution was stirred at -78 C for 1 h. To the reaction mixture, a solution of 2-(l-trityl-lH-imidazol-4-yl)benzaldehyde (700 mg, 1.69 mmol) in THF (10 mL) was added. After stirring for 2 h at -78 C the reaction was allowed to warm to rt and stirred for another 4 h at rt. The reaction was quenched by adding satd NH4CI solution (10 mL) and water (45 mL). The product was extracted with DCM (3x 50 mL), the combined organic extract was dried over Na2S04 and concentrated under reduced pressure to afford the crude, chromatographic purification afforded the desired product as white solid (618 mg, 45 %). NMR (400 MHz, Chloroform-^ delta 7.85 (s, 1H), 7.75 (d, J = 7.8 Hz, 1H), 7.60 (d, J= 7.7 Hz, 1H), 7.52 - 7.05 (m, 21H), 6.98 - 6.90 (m, 5H), 6.75 (d, J = 8.7 Hz, 4H), 4.32 - 4.03 (m, 4H), 3.78 (s, 6H).

Reference： [1]Patent: WO2019/6047,2019,A1 .Location in patent: Paragraph 0210; 0211; 0212

76
[ 1402838-08-7 ]
((3-bromo-5-fluorobenzyl)oxy)(tert-butyl)dimethylsilane [ No CAS ]
(3-(((tert-butyldimethylsilyl)oxy)methyl)-5-fluorophenyl)(2-(1-trityl-1H-imidazol-4-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%		To a solution of ((3-bromo-5-fluorobenzyl)oxy)(tert-butyl)dimethylsilane (105 mg, 0.579 mmol) in anhydrous THF (4 mL) at -78 C was added n-BuLi (0.24 mL, 0.531 mmol, 2.2 M solution cyclohexane). After stirring for 0.5 hr at -78 C, a solution of 2-(l-trityl-lH-imidazol- 4-yl)benzaldehyde (200 mg, 0.483 mmol) in THF (2 mL) was added and the reaction was allowed to warm to room temperature over a period of 2 hr and continued stirring ovemight (18 h). The reaction was quenched by adding satd. NH4CI (5 mL) and the reaction was diluted with water (30 mL), the product was extracted with DCM (3 x 40 mL). The combined organic extract was dried over Na2S04 and concentrated under reduced pressure, the crude was purified by column chromatography to give desired product as gel (520 mg, 79%). 1H NMR (400 MHz, Chloroform- delta 7.38 (dd, J= 5.2, 2.0 Hz, 11H), 7.35 - 7.29 (m, 7H), 7.09 - 7.03 (m, 7H), 5.86 (s, 1H), 4.63 (s, 2H), 0.90 (s, 9H).

Reference： [1]Patent: WO2019/6047,2019,A1 .Location in patent: Paragraph 0227; 0228; 0229

77
[ 1402838-08-7 ]
[1-(3-bromophenyl)ethoxy](tert-butyl)dimethylsilane [ No CAS ]
(3-(1-((tert-butyldimethylsilyl)oxy)ethyl)phenyl)(2-(1-trityl-1H-imidazol-4-yl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.5%		To a solution of (l-(3-bromophenyl)ethoxy)(tert-butyl)dimethylsilane (1.10 g, 3.47 mmol) in THF (15 mL) at -78 C was added n-BuLi (1.58 mL, 1.59 mmol; 2.2 M solution in hexanes). After stirring for 1.5 h, 2-(l-trityl-lH-imidazol-4-yl)benzaldehyde (900 mg, 2.17 mmol) was added as a solution in THF (6 mL). The mixture was allowed to warm to rt and stirred overnight. The reaction was diluted with water (30 mL) and the product was extracted with EtOAc (3 x 50 mL). The combined organic extract was washed with water (50 mL), dried over Na2S04 and concentrated under reduced pressure to afford the crude mixture. The crude was purified by CombiFlash to afford the desired product as white solid (1.28 g, 90.5 %). NMR (400 MHz, Chloroform-^ delta 7.47 - 7.01 (m, 24H), 6.88 (d, J = 10.9 Hz, 1H), 5.91 (s, 1H), 4.91 - 4.70 (m, 1H), 1.31 (dd, J = 6.2, 3.9 Hz, 3H), 0.84 (d, J = 20.4 Hz, 9H), -0.00 - -0.20 (m, 6H).

Reference： [1]Patent: WO2019/6047,2019,A1 .Location in patent: Paragraph 0249; 0250; 0251

78
[ 6952-59-6 ]
[ 1402838-08-7 ]
3-(hydroxy(2-(1-trityl-1H-imidazol-4-yl)phenyl)methyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%		To a solution of 3-bromobenzonitrile (659 mg, 3.62 mmol) in anhydrous THF (10 mL) at -78 C was added n-BuLi (1.45 mL, 3.63 mmol, 2.5 M solution in hexane). After stirring for 0.5 hr at -78 C, a solution of 2-(l-trityl-lH-imidazol-4-yl)benzaldehyde (1 g, 2.41 mmol) in THF (6 mL) was added and the reaction was allowed to warm to room temperature over a period of 2 hr and continued stirring overnight (18 hr). The reaction was quenched by adding satd. NH4CI (5 mL) and the reaction was diluted with water (30 mL), the product was extracted with DCM (2 x 30 mL). The combined organic extract was dried over Na2S04 and concentrated under reduced pressure. The crude was purified to obtain 0.6 g of product (48% yield). LCMS (ESI, m/z): 518.4 [M+H]+; 1H NMR (400 MHz, Chloroform-c delta 7.70 (d, J= 10.2 Hz, 1H), 7.58 (s, 3H), 7.52 (d, J= 7.6 Hz, 2H), 7.47 - 7.16 (m, 29H), 7.12 - 6.93 (m, 8H), 6.93 - 6.83 (m, 1H), 5.87 (s, 1H).

Reference： [1]Patent: WO2019/6047,2019,A1 .Location in patent: Paragraph 0260; 0261; 0262

79
[ 849203-60-7 ]
[ 1402838-08-7 ]
tert-butyl (2E)-1-oxo-2-([2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]methylidene)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With calcium hydroxide; In ethanol; at 80℃;	A slurry of tert-butyll-oxo-7-azaspiro [3.5jnonane-7-carboxylate (2.27 g, 9.49 mmol), 2-[1-(triphenylmethyi)-l H-imidazol-4-yl]benzaldehyde (4.04 g, 9.74 mnioi) and Ca(OH)2 (2.10 g, 28.33 mmol) in EtOH (100 mL) were mixed and stirred overnight at 80 C. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 7.4 g (crude) of tert-butyl(2E)-1 -oxo-2-([2-[ I -(tripbenylmethyl)-IN-imidazol-4-yI] phenyljmethylidene)-7- azaspiro[3.5]nonane-7-crboxy1ate as a yellow solid. LCMS (ESI) rniz 636.2 [M+HJ

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 142; 143

80
[ 1402838-08-7 ]
tert-butyl 2’-oxo-8-azaspiro[bicyclo[3.2.1]octane-3,1‘-cyclobutane]-8-carboxylate [ No CAS ]
tert-butyl (E)-2’-oxo-3'-(2-(1-trityl-1H-imidazol-4-yl)benzylidene)-8-azaspiro[bicyclo[3.2.1]octane-3,1‘-cyclobutane]-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With calcium hydroxide; In ethanol; at 80℃; for 24h;	A slurry of tert-butyl 2?-oxospiro[8-azabicyclo[3 .2.1 ]octane-3, I ?-cyclobutanej-8-carhoxylate (2.65 g, 9.98 .mmol), 2-[ 1.-(triphenylmethyl)- IH-imidazol-4-yl.]benzaldehyde (4.55 g,11.0 mmol) and Ca(OH)2 (1.48 g, 20.0 mmol) in EtOH (33 mL) was stirred for 24 h at 80 C.The reaction was cooled to room temperature and insoluble material was removed by filtration. The filtrate was concentrated. The residue was purified by a silica gel column eluting withDCM/methanoj. (90:10) to afford 5.60 g (85%) tertbutyl E)-2?-oxo-3?(2-(1-trity1-1Wirnidazo1.-4-yl)benzylidene)-8-azaspiro[bicyclo{3 .2.1 ]octane-3, 1 ?-cyclobutane]-S-carboxylate as a pale yellow solid. LCM.S (ESI) m/z 662.3 [M+F1]4.

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 342-344

81
[ 1402838-08-7 ]
8-thiaspiro[4.5]decan-1-one [ No CAS ]
(2E)-2-([2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]methylidene)-8-thiaspiro[4.5]decan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With calcium hydroxide; In ethanol; at 80℃; for 16h;	A solution of 8-thiaspiro[4.5]decan-1-one (700 rug, 4.11 ,mmol) and 2-[1- (triphenylmethyl)-IH-imidazol-4-yijhenzaldehyde (2.6 g, 6.27 mmol) in EtOH (10 mL) was added Ca(OH)2 (762 mg, 10.28 mmol). The resulting solution was stirred for 16 h. at 80 C. The mixture was concentrated under vacuum. The residue was purified by silica gel column eluting with PE/ EtOAc (1/1). This resulted in 2.3g (crude) of(2E-2-([2-[1.-(triphenyimethy1)-iH.- imidazol-4yl]phenyl]methy1idene)-8thiaspiro[4.5]decan I one as a yellow solid. LCMS (ESI) m/z 567.2 [M+Hf?.

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 384; 385

82
[ 1402838-08-7 ]
[ 191805-29-5 ]
tert-butyl (2E)-1-oxo-2-([2-[1-(triphenylmethyl)-1H-imidazol-4- yl]phenyl]methylidene)-8-azaspiro[4.5]decane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With calcium hydroxide; In ethanol; at 80℃; for 4h;	A mixture of <strong>[191805-29-5]tert-butyl 1-oxo-8-azaspiro[4.5]decane-8-carboxylate</strong> (3.0 g, 11.84mmol) and 2-[1-(triphenylmethyl)-1i-{-imidazol-4-yljbenzaldehyde (5.8 g, 13.99 mmol) in EtOH(100 mL was added Ca(OH)z (2.7 g, 36.44 nimol). The resulting solution was stirred for 4 h at80 C. The resulting mixture was concentrated under vacuum. The resulting solution was dilutedwith DCM (600 mL). The solid were filtered out. The filtration was concentrated under vacuum.The residue was purified by a silica gel column with EtOAc /PE (30%-80%). This resulted in 7.5g (97%) of tert-butyl (2E)- 1 -oxo-2-([2-[ 1 -(triphen.ylmethyl)- 1H-imidazoi-4-yl]phenyl]rnethylidene)-8-azaspiro[4.5]decane-8-carboxylate as a light yellow solid. LCMS (ES)ui/z - 650.3 [M+F{].

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 157; 158

83
[ 1402838-08-7 ]
tert-butyl 2’-oxo-3-azaspiro[bicyclo[3.2.1]octane-8,1‘-cyclobutane]-3-carboxylate [ No CAS ]
tert-butyl (E)-2’-oxo-3’-(2-(1-trityl-1H-imidazol-4-yl)benzylidene)-3-azaspiro[bicyclo[3.2.1]octane-8,1‘-cyclobutane]-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With calcium hydroxide; In ethanol; at 80℃; for 20h;	A slurry of tert-butyl 2?-oxospiro[3-azabicyclo[3.2. 1] octane-8, 1 ?..cyclobutanel-3- carboxylate (3.00 g, 1 .1.3 mmol), 2-[1 -(triphenylmethyl)-1H-imidazol4-yl]benzaldehyde (4.69 g, 11.3 mmol) and Ca(OH)2 (1.68 g, 22.6 mmol) in EtOH (57 mL) was stirred for 20 h at 80 C. The reaction was cooled to room temperature and insoluble material was removed by filtration. The filtrate was concentrated. The residue was purified by a silica gel column eluting with DCM/methanol (90:10) to afford 6.83 g (91%) tert-butyl (3 ?E)-T-oxo-3?-[[2-( 1 -tnitylimidazol-4- yl)phenyljmethylene] spiro[3-azabicyclo[3 .2.1 joctane-8, I ?-cyclobutanej-3-carboxylate as a colorless solid. LCMS (ES]) m/z = 662.3 M+H]

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 456; 457

84
[ 1402838-08-7 ]
[ 1581683-57-9 ]
tert-butyl (6E)-5-oxo-6-([2-[1-(triphenylmethyl)-1H-imidazol-4-yl]phenyl]methylidene)-2-azaspiro[3.4]octane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With calcium hydroxide; In ethanol; at 80℃; for 6h;	To a solution of tert-butyl 5-oxo-2-azaspiro[3.4]octane-2-carboxylate (2 g, 8.89 minol), 2-[ 1 -(triphenylmethyl)- I. H-iniidazol-4-y1]benzaldehyde (5.53 g, 13.34 mmol) and Ca(OH)2 (1.64g. 22.13 mniol) in EtOH (250 mL) was stirred for 6 hat 80C. The solids were filtered out. The solids were filtered out. The solvent was concentrated under vacuum. The residue was purified by silica gel column eluting with EtOAc /PE (1:2). This resulted in 5.24 g (95%) of tert-butyl (6E)-5-oxo-6-([2-[ 1 -(triphenyl.methyl)-1 H-imidazoi-4-yljphenyljmethylidene)-2-azaspiro[3.4]octane-2-carboxylate as a light yellow solid. LCMS (ESI)mJz = 622.8 [.M+Hr.

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 183; 184

85
[ 1402838-08-7 ]
tert-butyl 5-oxo-2-azaspiro[3.3]heptane-2-carboxylate [ No CAS ]
tert-butyl (E)-5-oxo-6-(2-(1-trityl-1H-imidazol-4-yl)benzylidene)-2-azaspiro[3.3]heptane-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With calcium hydroxide; In ethanol; at 20℃; for 1h;	To a mixture of tert-butyl 5-oxo-2-azaspiro[3.3jheptane-2-carboxylate (250 mg, 1.2 mmol) and 2-[ I .-(triphenylmethyl)-1I1-imidazol-4-yl]benzaldehyde (580 mg, 1.4 mmol) in EtOH (10 mL) was added Ca(OH)2 (270 mg, 3.6 mmol). The resulting solution was stirred for 1 h at room temperature. The resulting mixture was concentrated under vacuum. The resulting solution was diluted with DCM (600 mL). The solid were filtered out. The filtration was concentrated under vacuum. The residue was purified by a silica gel column with EtOAc /PE (30%-80%). This resulted in 700 mg (97%) of the title compound as a light yellow solid. LCMS (ESI) mlz = 608.2[M+Hj.

Reference： [1]Patent: WO2019/5559,2019,A1 .Location in patent: Paragraph 229; 230

86
[ 1402838-08-7 ]
[ 1029684-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In methanol; at 20℃;	General procedure: 1,1,1-Trifluoro-N-(3-(2-(1-trityl-1H-imidazol-4-yl)phenoxy)propyl)methanesulfonamide (11, 0.2 g,0.34 mmol) and AcOH (0.5 mL) were added to CH3OH (10 mL), and the reaction mixture was stirred at 20 C. After the starting material disappeared in thin layer chromatography (TLC), the reaction mixturewas distilled in vacuo, the product was purified as a white solid by silica gel column chromatography,0.101 g, yield 86%.

Reference： [1]Molecules,2019,vol. 24

87
[ 137052-08-5 ]
[ 1402838-08-7 ]
[ 1402838-19-0 ]

Reference： [1]Journal of Medicinal Chemistry,2019,vol. 62,p. 6705 - 6733

88
[ 1123-86-0 ]
[ 1402838-08-7 ]
C₃₈H₃₆N₂O [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2020,vol. 11,p. 541 - 549

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1402838-08-7	MDL No. :	MFCD29059355
Formula :	C₂₉H₂₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ARCOTNOWDCVWJS-UHFFFAOYSA-N
M.W :	414.50	Pubchem ID :	89052871
Synonyms :

Num. heavy atoms :	32
Num. arom. heavy atoms :	29
Fraction Csp3 :	0.03
Num. rotatable bonds :	6
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	127.66
TPSA :	34.89 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-4.63 cm/s

Log Po/w (iLOGP) :	3.59
Log Po/w (XLOGP3) :	5.91
Log Po/w (WLOGP) :	6.2
Log Po/w (MLOGP) :	4.18
Log Po/w (SILICOS-IT) :	6.09
Consensus Log Po/w :	5.19

[ CAS No. 1402838-08-7 ] {[proInfo.proName]}

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[ 1402838-08-7 ] Synthesis Path-Upstream 1~1

[ 1402838-08-7 ] Synthesis Path-Downstream 1~88

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[ 1402838-08-7 ]

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[ 1402838-08-7 ]

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Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-6.41
Solubility :	0.000162 mg/ml ; 0.000000391 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.42
Solubility :	0.000159 mg/ml ; 0.000000383 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-10.38
Solubility :	0.0000000172 mg/ml ; 0.0 mol/l
Class :	Insoluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.56

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
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P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 1402838-08-7 ] {[proInfo.proName]}

Quality Control of [ 1402838-08-7 ]

Related Doc. of [ 1402838-08-7 ]

Product Details of [ 1402838-08-7 ]

Calculated chemistry of [ 1402838-08-7 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1402838-08-7 ]

Application In Synthesis of [ 1402838-08-7 ]

[ 1402838-08-7 ] Synthesis Path-Upstream 1~1

[ 1402838-08-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 1402838-08-7 ]

Aryls

Aldehydes

Related Parent Nucleus of [ 1402838-08-7 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

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Environmental hazards

Inquiry

Related Functional Groups of
[ 1402838-08-7 ]

Related Parent Nucleus of
[ 1402838-08-7 ]