[ CAS No. 1310384-24-7 ] {[proInfo.proName]}

Name: 1310384-24-7|4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enol|95%
Brand: Ambeed
SKU: A148073
Price: 74.0 USD
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2D 3D

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Quality Control of [ 1310384-24-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1310384-24-7 ]

Product Details of [ 1310384-24-7 ]

CAS No. :	1310384-24-7	MDL No. :	MFCD12025483
Formula :	C₁₂H₂₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CJCRPHXXLKDDES-UHFFFAOYSA-N
M.W :	224.10	Pubchem ID :	67453403
Synonyms :

Calculated chemistry of [ 1310384-24-7 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	65.31
TPSA :	38.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.66
Log Po/w (WLOGP) :	2.09
Log Po/w (MLOGP) :	1.07
Log Po/w (SILICOS-IT) :	1.03
Consensus Log Po/w :	1.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.21
Solubility :	1.38 mg/ml ; 0.00618 mol/l
Class :	Soluble
Log S (Ali) :	-2.09
Solubility :	1.84 mg/ml ; 0.0082 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.1
Solubility :	1.78 mg/ml ; 0.00796 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.24

Safety of [ 1310384-24-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1310384-24-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1310384-24-7 ]

[ 1310384-24-7 ] Synthesis Path-Downstream 1~9

1
[ CAS Unavailable ]
[ 1802370-88-2 ]
[ 1310384-24-7 ]
[ 1802366-96-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-bromo-2-(1H-1,2,3,4-tetrazol-5-yl)-6-(trifluoromethyl)benzene-1-sulfonamide With tetrabutyl-ammonium chloride; potassium carbonate; p-methoxybenzyl chloride; sodium iodide In chloroform; water at 55℃; for 12h; Inert atmosphere; Stage #2: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-ol With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 85℃; Stage #3: potassium cyanide Further stages;	24.I; 497.A; 497.B; 497.C; 497.D; 497.E; 497.F Step F: 3-(4-Amino-4-(aminomethyl)cyclohexyl)-2-(1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide Step I: 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide (0386) Into a 10000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-bromo-2-(1H-1,2,3,4-tetrazol-5-yl)-6-(trifluoromethyl)benzene-1-sulfonamide (230 g, 618.08 mmol, 1.00 equiv), potassium carbonate (276 g, 2.00 mol, 3.23 equiv), NaI (18.4 g), Bu4NCl (34.0 g, 122 mmol, 0.20 equiv), chloroform (3800 mL, 1.00 equiv), 1-(chloromethyl)-4-methoxybenzene (380 g, 2.43 mol, 3.93 equiv), water (2550 mL). The resulting solution was stirred for 12 hr at 55° C. The aqueous phase was extracted with 2×1000 mL of DCM. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/ hexane (1:10). Purification afforded 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[1-[(4-methoxyphenyl)methyl]-1H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide, and 3-bromo-N,N-bis[(4-methoxyphenyl)methyl]-2-[2-[(4-methoxyphenyl)methyl]-2H-1,2,3,4-tetrazol-5-yl]-6-(trifluoromethyl)benzene-1-sulfonamide. (0387) LC-MS: (ES, m/z): 732 [M+H]+. (0388) H-NMR: (CDCl3, 300 Hz, ppm): δ 3.763 (9H, s), 3.820-3.872 (2H, d, J=15.6), 4.402-4.454 (2H, d, J=15.6), 5.154-5.203 (1H, d, J=14.7), 5.560-5.609 (1H, d, J=14.7), 6.702-6.763 (6H, m), 6.912-6.941 (4H, m), 7.109-7.138 (2H, m), 7.839-7.854 (2H, m). Step A: 4′-Hydroxy-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-4-(trifluoromethyl)-2′,3′,4′,5′-tetrahydro-[1,1′-biphenyl]-3-sulfonamide and 4′-hydroxy-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-4-(trifluoromethyl)-2′,3′,4′,5′-tetrahydro-[1,1′-biphenyl]-3-sulfonamide (1022) 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enol (1.2 g, 5.4 mmol), 3-bromo-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-bromo-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (2.5 g, 3.4 mmol), sodium carbonate (0.723 g, 6.83 mmol), PdCl2(dppf) (0.250 g, 0.341 mmol) were placed in a reaction vessel. Dioxane (25.6 mL) and water (8.53 mL) were added. The reaction mixture was degassed for 20 min and then heated at 85° C. overnight. LC-MS showed the reaction was completed. The reaction was then diluted with water and extracted with EtOAc. The organics were combined, washed with brine, separated and concentrated and the residue was purified by column chromatography (0-100% EtOAc/Hexane) to give the title compounds. LC/MS (M+1)+=750.6 Step D: 3-(4-Amino-4-cyanocyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(4-amino-4-cyanocyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (1025) N,N-bis(4-Methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-3-(4-oxocyclohexyl)-6-(trifluoromethyl)benzenesulfonamide and N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-3-(4-oxocyclohexyl)-6-(trifluoromethyl)benzenesulfonamide (300 mg, 0.400 mmol) in conc NH4OH/MeOH (1/1, 3 mL) was treated with KCN (52.1 mg, 0.800 mmol) and Ammonium Chloride (86 mg, 1.6 mmol). The mixture was heated in a sealed reaction vessel overnight. After cooling to rt, the reaction mixture was partitioned between EtOAc and water. The organic layer was separated and concentrated. The residue was purified by column chromatography (0-80% EtOAc/Hexane) to give the title compounds. LC/MS (M+1)+=776.6. Step E: 3-(4-Amino-4-(aminomethyl)cyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(4-amino-4-(aminomethyl)cyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (1026) 3-(4-Amino-4-cyanocyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(4-amino-4-cyanocyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (222 mg, 0.286 mmol) was dissolved in acetic acid (1.5 mL), EtOH (1 mL), and DCM (2 mL). Platinum(IV) Oxide (38 mg, 0.167 mmol) was added. The mixture was hydrogenated using a par shaker (40 psi) overnight. LC-MS showed the completion of the reaction. The reaction mixture was filtered and the filtrates were concentrated to give the crude title compounds, which were used directly in the next step. LC/MS (M+1)+=780.7. Step F: 3-(4-Amino-4-(aminomethyl)cyclohexyl)-2-(1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (1027) 3-(4-Amino-4-(aminomethyl)cyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(1-(4-methoxybenzyl)-1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide and 3-(4-amino-4-(aminomethyl)cyclohexyl)-N,N-bis(4-methoxybenzyl)-2-(2-(4-methoxybenzyl)-2H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide (223 mg, 0.286 mmol) was heated in TFA at 60° C. for 2 hr. The reaction mixture was concentrated and the residue purified with Gilson (2-45% CH3CN/water with 0.1% TFA) to afford 3-(4-amino-4-(aminomethyl)cyclohexyl)-2-(1H-tetrazol-5-yl)-6-(trifluoromethyl)benzenesulfonamide. LC/MS (M+1)+=420.3.

Reference： [1]Current Patent Assignee: MERCK & CO INC - US2016/333021, 2016, A1 Location in patent: Paragraph 0386; 0387; 0388; 1022; 1023; 1024; 1025; 1026; 20

2
[ 72254-60-5 ]
[ 1310384-24-7 ]
[ 2116442-42-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium phosphate; palladium diacetate; triphenylphosphine In 1,4-dioxane; water at 70 - 110℃; for 1.33333h; Inert atmosphere; Sealed tube;	2 Ethyl 2-amino-7-(4-hydroxycyclohex- 1-en-1-yl)-5-oxo-5H-chromeno j2,3-bj pyridine-3- carboxylate (46). A solution of tripotassium phosphate (701 mg, 3.3 mmol) in water (1.35 mL) was added to a nitrogen-degassed suspension of compound 1 (200 mg, 0.55 mmol), 4- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)cyclohex-3-en- 1-01 (136 mg, 0.61 mmol), triphenylphosphine (72.2 mg, 0.28 mmol), and Pd(Oac)2 (12.4 mg, 0.06 mmol) inp-dioxane (13.5 mL). The reaction vessel was sealed with a screw cap and heated at 100 -110 °C for 20 mm, and then stirred at 70 °C for 1 h. After cooling, the mixture was concentrated and theresidue was treated with a biphasic mixture of dichloromethane (150 mL) and water (30 mL). Precipitated solids were collected by filtration, washed with water and dried to give a first crop of product (137 mg). The dichloromethane phase of the filtrate was dried (Na2SO4) and concentrated to a solid that was triturated in dichloromethane and dried to give a second crop (42 mg). Total yield of 46 = 179 mg (85%). ‘H NMR (400 MI-Tz, chloroform-d): ö 9.16 (s,1H), 8.37 (s, 1H), 8.23 (d, J= 2.4 Hz, 1H), 7.77 (dd, J= 8.8, 2.4 Hz, 1H), 7.45 (d, J 8.8 Hz,1H), 6.13 (s, 1H), 5.84 (s, 1H), 4.41 (q,J= 7.1 Hz, 2H), 4.11 (s, 1H), 2.75-2.57 (m, 3H),2.31 -2.22 (m, 1H), 2.05 (s, 1H), 1.97 - 1.77 (m, 2H), 1.44 (t, J 7.1 Hz, 3H). MS TOFES:in/z 381.0 (M+H).
85%	With potassium phosphate; palladium diacetate; triphenylphosphine In 1,4-dioxane; water at 70 - 110℃; for 2.5h; Sealed tube;	Method A: Palladium-catalyzed cross coupling reactions General procedure: (a) Suzuki couplings[1]General Procedure: A nitrogen-degassed solution of a potassium base in water was addedto a nitrogen-degassed suspension of substrate aryl bromide, alk-1-en-1-yl/cycloalk-1-en-1-yl boronic acid/pinacol ester, trialkyl-/triphenylphosphine, and palladium catalyst in anorganic solvent. The reaction vessel was sealed with a screw cap and heated for aspecified time, generally resulting in a clear orange solution. Workup was carried out byconcentrating the mixture to a residue that was diluted with water and extracted withdichloromethane. Further workup left a residue that was purified by trituration in anappropriate solvent or by silica gel chromatography.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MICHIGAN - WO2017/132538, 2017, A1 Location in patent: Page/Page column 109; 110; 111
[2]Beyett, Tyler S.; Gan, Xinmin; Reilly, Shannon M.; Gomez, Andrew V.; Chang, Louise; Tesmer, John J.G.; Saltiel, Alan R.; Showalter, Hollis D. [Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 20, p. 5443 - 5461]

3
[ 1310384-24-7 ]
[ 2640093-94-1 ]
[ 2640093-96-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere;	113.2 Step 2. Step 2. 4-(3-(6-(4-Hydroxycyclohex-1-en-1-yl)pyridin-3-yl)-6-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-b]pyridin-5-yl)-2,3-dihydro-1H-indene-1-carbonitrile 4-(3-(6-Chloropyridin-3-yl)-6-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-b]pyridin-5-yl)-2,3-dihydro-1H-indene-1-carbonitrile (50 mg, 0.094 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-ol (32 mg, 0.141 mmol), Xphos-PdG2 (8 mg, 9.40 μmol) and K3PO4 (40 mg, 0.188 mmol) were placed in a vial with septum. The vial was evacuated and backfilled with N2 three times, 1,4-dioxane (1 mL) and water (0.2 mL) were added, and the reaction mixture was stirred at 100° C. for 1 h. The mixture was filtered. The filtrate was partitioned between water and EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by Biotage Isolera to afford the desired product. LC-MS calculated for C34H40N5O3Si (M+H)+: m/z=594.3; found 594.3.

Reference： [1]Current Patent Assignee: INCYTE CORP - US2021/106588, 2021, A1 Location in patent: Paragraph 1355-1356

4
[ 1310384-24-7 ]
[ 2654050-18-5 ]
[ 2654050-27-6 ]

Yield	Reaction Conditions	Operation in experiment
91.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	1.1 Step 1 : [4-(4-Hydroxycyclohexen-l-yl)thiazol-2-yl]-[l-(2-trimethylsilylethoxymethyl)indol-3- yljmethanone To a solution of (4-bromothiazol-2-yl)-[l-(2-trimethylsilylethoxymethyl)indol-3- yljmethanone (370 mg, 837.40 pmol, 1 eq) and 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-ol (187.66 mg, 837.40 pmol, 1 eq) in 1,4-dioxane (10 mL) and H2O (1 mL) were added Pd(dppf)Cl2 (61.27 mg, 83.74 pmol, 0.1 eq) and CS2CO3 (545.68 mg, 1.67 mmol, 2 eq). The mixture was stirred at 90 °C for 16 h under N2 atmosphere. TLC (PE/EtOAc = 1/1, Rf= 0.67) showed the starting material was consumed and a new spot was formed. The mixture was filtered and concentrated to give a residue which was purified by flash silica chromatography (PE/EtOAc = 3/1 to 1/1) to yield [4-(4-hydroxycyclohexen-l-yl)thiazol-2-yl]-[l-(2- trimethylsilylethoxymethyl)indol-3-yl]methanone (356 mg, 767.35 pmol, 91.6% yield, 98.0% purity) as yellow gum. NMR (500 MHz, CDCb) d ppm 9.09 (s, 1H), 8.58-8.53 (m, 1H), 7.59- 7.55 (m, 1H), 7.39-7.36 (m, 2H), 7.35 (s, 1H), 6.70 (br s, 1H), 5.61 (s, 2H), 4.14-4.10 (m, 1H), 3.58-3.55 (m, 2H), 2.76-2.57 (m, 3H), 2.35-2.30 (m, 1H), 2.12-2.06 (m, 1H), 1.95-1.86 (m, 1H), 0.98-0.88 (m, 2H), -0.05 (s, 9H; ES-LCMS m/z 455.3 [M+H]+.

Reference： [1]Current Patent Assignee: IKENA ONCOLOGY INC - WO2021/127302, 2021, A1 Location in patent: Paragraph 00162; 00275

5
[ 1310384-24-7 ]
[ 2751719-98-7 ]
[ 2751718-87-1 ]

Yield	Reaction Conditions	Operation in experiment
79.7%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 3h; Inert atmosphere;	33.1 4-(4-((R)-1-(3-(difluoromethyl)-2-fluorophenyl)ethyl)amino)-2-Methyl-8,9-dihydrofuro[2,3-h]quinazolin-6-yl)cyclohex-3-enol 33b Compound 24d (200 mg, 0.4 mmol),Compound 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)cyclohex-3-enol 33a (179 mg, 0.8 mmol, Shanghai Bide ), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (32 mg, 39 μmol) and anhydrous sodium carbonate (85 mg, 800 μmol) were dissolved in 6 mL of 1, 4-dioxane and 2 mL of water were replaced with nitrogen three times, and heated to 100° C. to react for 3 hours. Cooled to room temperature, filtered through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with eluent system C to give the title compound 33b (150 mg), yield: 79.7%.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2021/249475, 2021, A1 Location in patent: Page/Page column 118; 119

6
[ 1310384-24-7 ]
[ 2751720-47-3 ]
[ 2751720-26-8 ]

Yield	Reaction Conditions	Operation in experiment
48.3%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 4h; Inert atmosphere;	102.1 4-(4-(((R)-1-(3-(difluoromethyl)-2-fluorophenyl)ethyl)amino)-2,10-Dimethyl-9,10-dihydro-8H-[1,4]oxazino[2,3-h]quinazolin-6-yl)cyclohex-3-enol 102a Compound 42b (0.2 g, 416 μmol) and compound 33a (140 mg, 625 μmol) were dissolved in 1,4-dioxane (3 mL) and water (0.6 mL),[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (34 mg, 42 μmol) and anhydrous sodium carbonate (90 mg, 849 μmol) were added sequentially, and nitrogen was replaced 3 times , heated to 100 °C for 14 hours. Cooled to room temperature, filtered through celite, the filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography with eluent system A to give the title compound 102a (100 mg), yield: 48.3%.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2021/249475, 2021, A1 Location in patent: Page/Page column 177

7
[ 1310384-24-7 ]
[ 2751721-29-4 ]
[ 2751721-38-5 ]

Yield	Reaction Conditions	Operation in experiment
64%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 100℃; for 3h; Inert atmosphere;	110.5 4-(2-Chloro-4-(((R)-1-(3-(difluoromethyl)-2-fluorophenyl)ethyl)amino)-8,9-dihydrofuro[2, 3-h]quinazolin-6-yl)cyclohexyl-3-enyl-1-ol 110e Compound 110d (68.00 mg, 0.14 mmol), compound 33a (35.46 mg, 0.16 mmol),[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (23.50 mg, 0.028 mmol) and sodium carbonate (30.49 mg, 0.29 mmol) were dissolved in water (0.40 mL) and dioxane (1.60 mL) were reacted under nitrogen atmosphere at 100°C for 3 hours, the reaction solution was concentrated under reduced pressure and purified by silica gel column chromatography with eluent system A to obtain the title compound 110e (45.1 mg) in 64% yield.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2021/249475, 2021, A1 Location in patent: Page/Page column 185; 186

8
[ 1310384-24-7 ]
[ 2751721-33-0 ]
[ 2751721-34-1 ]

Yield	Reaction Conditions	Operation in experiment
95.9%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; for 16h; Inert atmosphere;	112.6 4-(4-(((R)-1-(3-(difluoromethyl)-2-fluorophenyl)ethyl)amino)-2-Methylfuro[3',2':4,5]pyrido[3,2-d]pyrimidin-6-yl)cyclohex-3-en-1-ol 112h Compound 112g (172mg, 422.8μmol),Compound 33a (190 mg, 847.8 μmol),[1,1'-Bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (35 mg, 42.8 μmol) and anhydrous sodium carbonate (100 mg, 943.5 μmol) were dissolved in 6 mL of 1, 4-dioxane and 2 mL of water were replaced with nitrogen three times, and heated to 110° C. to react for 16 hours. Cooled to room temperature, filtered through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography with eluent system C to give the title compound 112h (190 mg), yield: 95.9%.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2021/249475, 2021, A1 Location in patent: Page/Page column 188; 190

9
[ 1310384-24-7 ]
[ 2755415-50-8 ]
[ 2755415-29-1 ]

Yield	Reaction Conditions	Operation in experiment
62.1%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct; anhydrous sodium carbonate In 1,4-dioxane; lithium hydroxide monohydrate at 80℃; for 14h; Inert atmosphere;	18.5 4-(((R)-1-(3-(difluoromethyl)-2-fluorophenyl)ethyl)amino)-6-(4-hydroxycyclohexyl-1-en-1-yl)- 2-Methylpyrido[2,3-d]pyrimidin-7(8H)-one 18d Compound 2c (850 mg, 1.98 mmol), compound 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)cyclohex-3-enol (891.7 mg, 3.98 mmol, Shaoyuan, Shanghai), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex (162.3 mg, 198.9 μmol) and anhydrous Sodium carbonate (421.7 mg, 3.98 mmol) was dissolved in 5 mL of dioxane and 1 mL of water, replaced with nitrogen three times, and reacted at 80° C. for 14 hours. Cooled to room temperature, filtered through celite, the filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography with eluent system A to give the title compound 18d (550 mg), yield: 62.1%.

Reference： [1]Current Patent Assignee: JIANGSU HENGRUI MEDICINE CO., LTD. - WO2021/249519, 2021, A1 Location in patent: Page/Page column 56-58

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[ CAS No. 1310384-24-7 ] {[proInfo.proName]}

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[ 1310384-24-7 ] Synthesis Path-Downstream 1~9

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Organoboron

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