[ CAS No. 248924-59-6 ]

Name: 248924-59-6|2-(3-Furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane|98%
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Product Details of [ 248924-59-6 ]

CAS No. :	248924-59-6	MDL No. :	MFCD03453669
Formula :	C₁₀H₁₅BO₃	Boiling Point :	255°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	194.04 g/mol	Pubchem ID :	2773996
Synonyms :

Safety of [ 248924-59-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 248924-59-6 ]

Upstream synthesis route of [ 248924-59-6 ]
Downstream synthetic route of [ 248924-59-6 ]

[ 248924-59-6 ] Synthesis Path-Upstream 1~4

1
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
[ 248924-59-6 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651

2
[ 22037-28-1 ]
[ 73183-34-3 ]
[ 248924-59-6 ]

Yield	Reaction Conditions	Operation in experiment
11%	With meso-tetra(p-tolyl)porphinato-palladium(II); potassium acetate In 1,4-dioxane at 110℃; for 15 h;	General procedure: Aryl/heteroaryl bromide 1 (1 mmol), B2pin2(2), B2npg2(4) orBpin (6, 1.2 mmol), and dioxane (5 mL) are taken into a 25 mLround-bottomed flask. KOAc (2 mmol) was added and stirredthe resultant mixture at room temperature for 5 min, PdII-TpTP(0.15 molpercent) was added, and the contents were refluxed on preheatedoil bath at 110 °C under constant stirring in open-air.The reaction progress was ensured by TLC. After completion ofthe reaction, the mixture was cooled, dilute with water (20 mL)and extracted with tertbutylmethyl ether (3 × 10 mL). The combinedn-hexane layers were concentrated, and the crudeproduct obtained was purified by column chromatography (CC)on silica gel using a mixture of ethyl acetate and hexane (1:30)as eluent.

Reference： [1] Organic Letters, 2014, vol. 16, # 17, p. 4562 - 4565
[2] Journal of the American Chemical Society, 2017, vol. 139, # 2, p. 607 - 610
[3] Synlett, 2018, vol. 29, # 8, p. 1055 - 1060

3
[ 76-09-5 ]
[ 55552-70-0 ]
[ 248924-59-6 ]

Reference： [1] Journal of the American Chemical Society, 2015, vol. 137, # 3, p. 1330 - 1340

4
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
[ 248924-59-6 ]

Reference： [1] Tetrahedron Letters, 2002, vol. 43, # 32, p. 5649 - 5651

[ 248924-59-6 ] Synthesis Path-Downstream 1~26

1
[ 110-00-9 ]
[ 73183-34-3 ]
[ 374790-93-9 ]
[ 248924-59-6 ]
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 5649 - 5651

2
[ 952289-07-5 ]
[ 248924-59-6 ]
[ 952289-09-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,2-dimethoxyethane; water; at 120℃; for 0.333333h;Microwave;	1,1-Dimethylethyl (2R,6S)-4-[6-[(4-bromo-2-chlorophenyl)sulfonyl]amino}-5-(methyloxy)-2-pyridinyl]-2,6-dimethyl-1-piperazinecarboxylate (D13) (0.15 g, 0.254 mmol), 2-(3-furanyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.0739 g, 0.381 mmol), Palladium dichloride di-triphenylphosphine (9.0 mg, 0.0127 mmol), sodium carbonate (0.053 g, 0.508 mmol) were heated in DME (2 mL) and water (1 mL) at 120 C. in the microwave for 20 minutes. The reaction was then diluted with ethyl acetate (50 mL) and washed with saturated sodium hydrogen carbonate (2×30 mL) and brine (30 mL). The organic layer was dried (MgSO4) and evaporated to give a yellow oil which was purified by chromatography [silica gel, eluting with 0 to 60% Ethyl acetate/pentane]. Product fractions evaporated to give a pale yellow foam (D15) (0.170 g) MS (ES+) m/e 577/579 [M+H]+.

Reference： [1]Patent: US2007/238737,2007,A1 .Location in patent: Page/Page column 13

3
[ 1003845-84-8 ]
[ 248924-59-6 ]
C₂₉H₃₄ClF₃N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 95℃; for 3h;	Example 33: Synthesis of 4-[(3-chloro-5-trifluoromethyl-benzyl)-(5-furan-3-yl- pyrimidin-2-yl)-amino]-2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester; A mixture of 4-[(5-bromo-pyrimidin-2-yl)-(3-chloro-5-trifluoromethyl-benzyl)-amino]- 2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester (0.1 mmol, 59 mg), 2-furan-3-yl- 4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolane (0.15 mmol, 29 mg), tetrakis(triphenylphosphine)palladium(0) (0.01 mmol, 11.5 mg) and sodium hydrogen carbonate (0.2 mmol, 17 mg) in 1 ,2-dimethoxy-ethane (1 ml_) and water (0.4 mL) is allowed to warm to 95 0C and stirred for 3 hours. The mixture is cooled to room temperature and then added water. The mixture is extracted with CH2CI2. The combined organic layer is washed with brine, dried over Na2SO4, filtrated, and concentrated under reduced pressure. The obtained residue is purified by silica gel column chromatography (eluent: hexane / EtOAc) to give 4-[(3-Chloro-5-trifluoromethyl-benzyl)-(5-furan-3-yl-pyrimidin-2-yl)-amino]- 2,6-diethyl-piperidine-1-carboxylic acid isopropyl ester (34 mg, 59%); ESI-MS m/z: 579 [M+1] Retention time 2.60 min (condition A).

Reference： [1]Patent: WO2008/9435,2008,A1 .Location in patent: Page/Page column 103

4
[ 56634-50-5 ]
[ 248924-59-6 ]
4-(furan-3-yl)furan-2(5H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With potassium fluoride; tetra-(n-butyl)ammonium iodide;trans-bis(triphenylphosphine)palladium dichloride; In water; toluene; for 12h;Heating / reflux;	Example 10; 4-(Furan-3 '-yl)furan-2(5H)-one 10; A mixture containing 4-bromo-5(H)furanone (0.261 g, 1.602 mmol), pinacolate(3- furanboronic) ester (0.392 g, 2.020 mmol), trans- dichlorobis(triphenylphosphine)palladium (II) (0.058 g, 8.263xlO'2 mmol), tetrabutylammonium iodide (0.062 g, 1.678XlO"1 mmol) and potassium fluoride (0.393 g, 6.764 mmol) in toluene (10 mL) and water (10 mL) were gently refluxed for 12 h under nitrogen before the reaction mixture was allowed to cool to room temperature. Brine (50 mL) was added and the product extracted with dichloromethane (3x20 mL). The organic fractions were combined, washed with brine (3x20 mL), dried over anhydrous magnesium sulfate and evaporated to dryness under reduced pressure to give a dark brown solid. The resulting solid was chromatographed (silica gel: eluent 50:50 dichloromethane/light petroleum followed by 100% dichloromethane) to give 4-(3 '-furan)furan-2(5H)-one 10 (0.043 g, 18%) as brown needles, m.p. 101-1020C (ref. PDS-2-11). UV- Vis lambdamax (MeOH) 244(1724) nm; 1H NMR (CDCl3, 300 MHz) delta 7.73 (s, IH, H21), 7.53 (t, IH, J = 1.5 Hz, H51), 6.60 (t, IH, J = 1.1 Hz, H3), 6.11 (t, IH, J= 1.5 Hz, H41), 5.06 (d, 2H, J= 1.9 Hz, H5); 13C NMR (CDCl3, 75 MHz) delta 173.7 (C2), 156.2 (C4), 145.0 (C41), 141.9 (Cl'), 117.5 (C21), 112.4 (C3), 108.2 (C31), 70.8 (C5); IR (KBr) 3141, 3114, 3051, 1790, 1736, 1673, 1519, 1470, 1447, 1405, 1355, 1322, 1275, 1236, 1158, 1019, 894, 871, 852, 828, 752, 702, 644, 596, 547, 527, 501 ran 1.

Reference： [1]Patent: WO2008/40097,2008,A1 .Location in patent: Page/Page column 28

5
[ 932024-64-1 ]
[ 248924-59-6 ]
[ 932024-76-5 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 1541 - 1544

6
[ 1001112-18-0 ]
[ 248924-59-6 ]
C₁₉H₁₇NO₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 9008 - 9011

Yield	Reaction Conditions	Operation in experiment
		3-(4,4,5,5-Tetramethyl-[1,3,2]-dioxaborolan-2-yl)-furan is prepared as follows: t-BuLi (40 mL of 1.7 M solution, 68 mmol) is added dropwise to a solution of 3-bromofuran (5.0 g, 34 mmol) in 100 mL of THF at -78 C., and the reaction mixture is stirred at -78 C. for 5 min. B(O-i-Pr)3 (23 mL, 100 mmol) is added, the cooling bath is removed, and the reaction mixture is stirred at room temperature for 18 h, and then cooled to 0 C. The reaction mixture is then quenched with 50 mL of 2N HCl, and extracted three times with EtOAc. The organic phases are combined, and washed with brine, dried over MgSO4, filtered, and concentrated. The residue is dissolved in 200 mL of CH2Cl2. Pinnacol (20 g), and Na2SO4 (100 g) are added, and the mixture is stirred at room temperature overnight, and then filtered. The solution is concentrated and purified by chromatography on silica gel (gradient elution with 10-40% EtOAc/hexane) to provide the desired product as a yellow solid; mp 52-55 C.; 1H NMR (250 MHz, CDCl3) delta7.78 (s, 1H), 7.46 (dd, 1H), 6.59 (d, 1H), 1.32 (s, 12H); IR (CH2Cl2, cm-1) 1300, 1269, 1138.

9
[ 68819-84-1 ]
[ 248924-59-6 ]
[ 880158-62-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 80℃; for 12h;	To a mixture of <strong>[68819-84-1]tert-butyl N-(4-bromobenzyl)carbamate</strong> (0.14 g), 2-(furan-3-yl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane (0.12 g), potassium carbonate (0.1 g), water (0.2 mL) and N,N-dimethylformamide (1 mL) was added tetrakis(triphenylphosphine)palladium(0) (0.03 g), and the resulting mixture was stirred at 80 C. for 12 hours. The reaction mixture was cooled to room temperature and then the insoluble material was filtered out. The filtrate was partitioned between ethyl acetate (110 mL) and water (50 mL). The organic layer was washed successively with water (50 mL) and brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on aminopropylated silica gel (eluent: hexane/ethyl acetate=1/1) to give tert-butyl N-[4-(furan-3-yl)benzyl]-carbamate. The compound obtained was dissolved in dichloromethane (5 mL), trifluoroacetic acid (0.57 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 2 hours. Saturated aqueous sodium hydrogen carbonate (15 mL) was added dropwise and the whole was extracted with dichloromethane (30 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate/brine (1/1, 10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the title compound (0.06 g).

Reference： [1]Patent: US2007/179115,2007,A1 .Location in patent: Page/Page column 35

10
[ 890315-74-9 ]
bis (acetato) triphenylphosphine palladium(II) [ No CAS ]
[ 248924-59-6 ]
2-(benzamido)-4-(furan-3-yl)benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium carbonate; In ethanol; N,N-dimethyl acetamide; ethyl acetate;	Example 14 61 mg of <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong>, 55 mg of sodium carbonate and 30 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of methyl 2- (benzamido) -4-bromobenzoate, and stirred at 90C for 12 hours. After the reaction mixture was cooled to room temperature, 41 mg of <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> and 22 mg of sodium carbonate were added and stirred at 90C for 12 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 1.0 mol/L hydrochloric acid were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 1.0 mol/L hydrochloric acid and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 2.0 mL of ethanol were added to the obtained residue and stirred at room temperature for 1 hour. 0.6 mol/L hydrochloric acid was added to the reaction mixture, and solid substances were separated by filtration and purified with reversed-phase silica gel column chromatography [eluent; 50-100% acetonitrile /0.1% trifluoroacetic acid aqueous solution] to obtain 6.2 mg of 2-(benzamido)-4-(furan-3-yl)benzoic acid as white solid. 1H-NMR (DMSO-d6) delta: 6.97 (1H, d, J = 1.7 Hz), 7.47 (1H, dd, J = 8.3, 1.7 Hz), 7.59-7.69 (3H, m), 7.83 (1H, t, J = 1.6 Hz), 7.98-8.00 (2H, m), 8.06 (1H, d, J = 8.3 Hz), 8.32 (1H, s), 8.94 (1H, d, J = 1.7 Hz), 12.29 (1H, s).

Reference： [1]Patent: EP1820795,2007,A1

11
[ 248924-59-6 ]
[ 566163-88-0 ]
[ 1036714-47-2 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 5139 - 5146

12
[ 1158649-25-2 ]
[ 248924-59-6 ]
[ 1158649-35-4 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2430 - 2433
[2]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 7931 - 7939

13
[ 1108740-07-3 ]
[ 248924-59-6 ]
[ 1201898-95-4 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 9956 - 9960

14
(4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone [ No CAS ]
[ 248924-59-6 ]
{4-[4-(4-furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 110℃;Sealed tube;	Example 9 Synthesis of {4-[4-(4-Furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (Compound 9) A mixture of (4-hydroxy-piperidin-1-yl)-{4-[4-(4-iodobenzotriazol-1-yl)-pyrimidin-2-yl-amino]-cyclohexyl}-methanone (274 mg) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-furan (102 mg) was placed in a screw cap pressure flask, and Na2CO3 (2 M aq, 0.7 mL, degassed), toluene (5 mL, degassed) and EtOH (5 mL) added. To this was added Pd(PPh3)4 (20 mg), the flask sealed, and the mixture stirred overnight at 110 C. The reaction mixture was then cooled to RT, diluted in water, extracted in DCM, washed with water and brine, dried over Na2SO4, and the solvent stripped to yield a crude solid. The crude product was chromatographed on silica, and eluted with 0-60% Magic Base/DCM, titurated in Et2O overnight, filtered, and evaporated to yield {4-[4-(4-furan-3-yl-benzotriazol-1-yl)-pyrimidin-2-ylamino]-cyclohexyl}-(4-hydroxy-piperidin-1-yl)-methanone (Compound 9, 103 mg). mp=243.0-244.0 C.; M+H=488.

Reference： [1]Patent: US2010/160360,2010,A1 .Location in patent: Page/Page column 17

15
[ 24423-87-8 ]
[ 248924-59-6 ]
[ 1229227-12-6 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 2690 - 2693

16
(1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-15-[[(2R)-2-amino-2,3-dimethylbutyl]oxy]-14-(5-bromo-1H-1,2,4-triazol-1-yl)-8-[(1R)-1,2-dimethylpropyl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid trifluoroacetate [ No CAS ]
[ 76-05-1 ]
[ 248924-59-6 ]
(1S,4aR,6aS,7R,8R,10aR,10bR,12aR,14R,15R)-15-[[(2R)-2-amino-2,3-dimethylbutyl]oxy]-8-[(1R)-1,2-dimethylpropyl]-14-[5-(3-furanyl)-1H-1,2,4-triazol-1-yl]-1,6,6a,7,8,9,10,10a,10b,11,12,12a-dodecahydro-1,6a,8,10a-tetramethyl-4H-1,4a-propano-2H-phenanthro[1,2-c]pyran-7-carboxylic acid trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A suspension of (1S,4aR,6aS,7/e,8R,10aR,10bi?,12aR,14/,15R)-15-[[(2R)-2- amino-2,3-dimethylbutyl]oxy]- 14-(5-bromo-7H- 1 ,2,4-triazol- 1 -yl)-8-[( 1R)- 1 ,2-dimethylpropyl]- 1 ,6,6a,7,8,9, 10, 10a, 10b, 11,12,12a-dodecahydro- 1 ,6a,8, 10a-tetramethyl-4H- 1 ,4a-propano-2H- phenanthro[1,2-c]pyran-7-carboxylic acid (Example 6B, 7.8 mg, 0.011 mmol), cesium carbonate (139 mg, 0.427 mmol), <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> (24 mg, 0.124 mmol), palladium (II) acetate (3.5 mg, 0.016 mmol) and 2-dicyclohexylphosphino-2',4',6'- triisopropylbiphenyl (2.2 mg, 0.005 mmol) in ethanol (0.2 mL) and water (0.1 mL) was blanketed with nitrogen and placed in a 80C oil bath for 2.5 hours. The mixture was cooled to room temperature, filtered and purified by reverse phase EtaPLC using a 19 x 150 mm Sunfire Preparative C18 OBD column eluting with acetonitrile/water + 0.1% TFA. Product fractions were evaporated and freeze-dried from a mixture of ethanol and benzene to give the title compound as a TFA salt (2.0 mg)1H NMR (CD3OD, 600MHZ, ppm) delta 0.76 (s, 3H, Me), 0.77 (d, 3H, Me), 0.77 (s, 3H, Me), 0.78 (d, 3H, Me), 0.80 (d, 3H, Me), 0.86 (d, 3H, Me), 0.87 (s, 3H, Me), 0.89 (d, 3H, Me), 1.16 (s, 3H, Me), 1.21 (s, 3H, Me), 1.23-1.34 (m), 1.40-1.44 (m), 1.48-1.72 (m), 1.82-2.02 (m), 2.12-2.21 (m), 2.41 (dd, 1H, H13), 2.84 (s, 1H, H7), 2.86 (d, 1H), 3.46 (d, 1H), 3.50 (d, 1H), 3.57 (dd, 1H), 3.68 (d, 1H), 3.91 (d, 1H), 3.93 (d, 1H), 5.53 (dd, 1H, H5), 5.90 (m, 1H, H14), 6.91 (d, furan), 7.74 (dd, furan), 8.07 (br s) and 8.13 (br s, 1H).Mass spectrum: (ESI) mJz = 705.42 (M+H).

Reference： [1]Patent: WO2010/19204,2010,A1 .Location in patent: Page/Page column 222

17
[ 1190221-99-8 ]
[ 248924-59-6 ]
[ 1190222-68-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 8h;Reflux;Product distribution / selectivity;	(ii) 5-Chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid·methyl ester; Using the same method as in Example 5-(i), <strong>[248924-59-6]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan</strong> was reacted with the 2-[((2-[(3-bromophenyl)amino]-2-oxoethoxy)acetyl)amino]-5-chlorobenzoic acid·methyl ester obtained in Example 19-(i) to give 5-chloro-2-([(2-([3-(furan-3-yl)phenyl]amino)-2-oxoethoxy)acetyl]amino)benzoic acid·methyl ester (yield: 75%).

Reference： [1]Patent: EP2272822,2011,A1 .Location in patent: Page/Page column 73

18
[ 1157928-89-6 ]
[ 248924-59-6 ]
[ 1190222-25-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With caesium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; for 22h;Reflux;	(i) N-Ethyl-5-(furan-3-yl)-2-methylaniline 0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%). 1H-NMR (CDCl3) delta: 1.33 (3H, t, J = 7.0 Hz), 2.14 (3H, s), 3.24 (2H, q, J = 7.0 Hz), 3.40 (1H, br), 6.67-6.71 (2H, m), 6.78 (1H, dd, J= 7.6, 1.8 Hz), 7.04 (1H, d, J = 7.6 Hz), 7.44-7.45 (1H, m), 7.67-7.69 (1H, m).

Reference： [1]Patent: EP2272822,2011,A1 .Location in patent: Page/Page column 60-61

19
[ 1206907-38-1 ]
[ 248924-59-6 ]
[ 1261352-04-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 5628 - 5634

20
[ 26340-49-8 ]
[ 248924-59-6 ]
[ 1187338-07-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate;palladium diacetate; In 1-methyl-pyrrolidin-2-one; water; at 25 - 110℃; for 0.283333h;Microwave irradiation;	Example 1.11 : 2-(Furan-3-yl)-1H-indole.A mixture of 2-iodo-1 /-/-indole (0.25 g, 0.001 mol) [2-iodo-1 H- indole is prepared according to literature: Bergman, J.; Venemalm, L. Efficient synthesis of 2-chloro-, 2-bromo-, and <strong>[26340-49-8]2-iodoindole</strong>. J. Org. Chem. 1992, 57, 2495-2497], furan-3-boronic acid pinacol ester (0.26 g, 0.00134 mol), palladium (II) acetate (10%, 0.03 g, 0.000134 mol) and potassium carbonate (0.18 g, 0.00134 mol) in 1-methyl-2-pyrrolidone (2.3 ml_) containing 0.18 mL of water is treated by microwave irradiation at 200 W in closed vessel at 110C per 15 min (temperature ramp from 25C to 1 10C in 2 minutes). After cooling the mixture is diluted with water under stirring and extracted with ethyl acetate. The organic layer is washed with water and dried. After solvent removal the solid residue is purified by column chromatography (silica gel, ethyl acetate: n- hexane 1 :5 as eluent) to give 2-(furan-3-yl)-1 /-/-indole (0.18 g, 95%), melting point 145-148C (after ethanol crystallization). 1H NMR (CDCI3): 5 6.61-6.62 (m, 1 H), 6.70-6.71 (m, 1 H), 7.09-7.19 (m, 2H), 7.36 (dd, J = 0.87 and 8.0 Hz, 1 H), 7.50-7.52 (m, 1 H), 7.58-7.60 (m, 1 H), 7.75 (m, 1 H), 8.10 ppm (br s, 1 H, it disappears after treatment with D2O). IR: v 3417 cm"1. Anal. (C12H9NO (183.21)) C, H, N.

Reference： [1]Patent: WO2011/121629,2011,A1 .Location in patent: Page/Page column 21
[2]Journal of Medicinal Chemistry,2011,vol. 54,p. 8394 - 8406

21
[ 62968-37-0 ]
[ 248924-59-6 ]
[ 1351933-94-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; lithium hydroxide; In 1,4-dioxane; water; at 80℃; for 0.5h;Inert atmosphere;	General procedure: To a solution of 2-chloroheteroaryl compound 1 (0.50 mmol) in 1,4-dioxane (4.0 mL) were added pinacol boronate 3, 5, or 7 (0.60 mmol), Pd(OAc)2 (1.1 mg, 5.0 mumol), S-Phos (4.1 mg, 10.0 mumol), and 2 M LiOH solution (1.0 mL, 2.0 mmol) at room temperature, and the mixture was stirred for 30 min at 80 C under N2 atmosphere. The reaction was quenched by adding water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica-gel column chromatography. The solvent was removed in vacuo, and the residue was triturated with Et2O to give biaryl compounds.

Reference： [1]Tetrahedron,2012,vol. 68,p. 272 - 279

22
[ 59247-47-1 ]
[ 248924-59-6 ]
tert-butyl 4-(furan-3-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃; for 12h;Inert atmosphere;	tert-butyl 4- furan-3-yl)benzoate. A mixture of 2-(furan-3-yl)-4,4,5,5-tetramethyl-l,3-dioxolane (379mg, 1.95 mmol), tert-butyl 4-bromobenzoate (500 mg, 1.95 mmol), sodium carbonate (621 mg, 5.86 mmol), tetrakis(triphenyl phosphine)palladium(O) (12 mg, 0.01 mmol) in a mixed solvent of 1 ,4-dioxane (16 ml) and water (4 ml) was stirred for 12 hours at 90°C under nitrogen atmosphere. After cooling to room temperature, the mixture was concentrated. The residue was purified by preparative-HPLC to give 2-a as a yellow oil (400 mg, 84percent). LRMS (M + H+) mlz: calcd 244.11; found 244. 1H NMR (300MHz, CD3OD): delta 8.02 (s, 1H), 7.95 (d, J= 8.1 Hz, 2H), 7.64 (d, J= 8.4 Hz, 2H), 7.60 (s, 1H), 6.87 (s, 1H), 1.61 (s, 9H).
83%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 90℃;Inert atmosphere;	To a stirred solution of tert-butyl 4-bromobenzoate (1.934 g, 7.53 mmol) in dioxane (62 mL) under argon was added 2-(furan-3-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.464, 7.53 mmol), sodium carbonate (2.398g, 22.6 mmol) and distilled water (15.5 mL). The mixture was degassed with argon before addition of palladium tetrakis-triphenylphosphine (46.3 mg, 0.039 mmol). The reaction was heated at 90 °C overnight. The crude reaction mixture was poured onto water and extracted with EtOAc (3X). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by flash chromatography (10-20percent DCM in hexanes eluent) to provide tert-butyl 4-(furan-3-yl)benzoate (1.52g, 83percent yield) as a colorless oil. 1H NMR (300 MHz, Chloroform-d) delta 8.00 (d, J = 8.7 Hz, 2H), 7.82 (dd, J = 1.5, 0.9 Hz, 1H), 7.59 - 7.47 (m, 3H), 6.75 (dd, J = 1.9, 0.9 Hz, 1H), 1.62 (s, 9H).

Reference： [1]Patent: WO2013/75083,2013,A1 .Location in patent: Paragraph 00154
[2]Patent: WO2018/136935,2018,A1 .Location in patent: Paragraph 00557

23
[ 73781-91-6 ]
[ 248924-59-6 ]
[ 1637587-09-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 110℃;Inert atmosphere;	General procedure: To 1,4-dioxane (15 mL) were added chloro-substituted N-heterocycles(10.0 mmol), aromatic boronic acid (or pinacol ester, 12.0 mmol), Pd(dppf)Cl2 (0.73 g, 1.0mmol) and aqueous Cs2CO3 (2 N, 10 mL, 20.0 mmol) under N2 atmosphere. The content washeated and kept at 110 °C overnight. The reaction mixture was cooled to room temperature after the completion of the reaction. Dioxane was removed under reduced pressure. The resultant aqueous solution was extracted with EtOAc. The combined organic phase was washed with water and saturated brine for three times, and dried over Na2SO4. After the removal of the solvent under reduced pressure, the residue was charged to flash chromatography, which gave the pure product.

Reference： [1]ARKIVOC,2014,vol. 2014,p. 72 - 93

24
[ 16870-28-3 ]
[ 248924-59-6 ]
4-(furan-3-yl)-2-hydroxybenzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7144 - 7167

25
[ 1458-01-1 ]
[ 248924-59-6 ]
methyl 3,5-diamino-6-(furan-3-yl)pyrazine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In methanol; toluene;Inert atmosphere; Reflux;	General procedure: <strong>[1458-01-1]Methyl 3,5-diamino-6-chloropyrazine-2-carboxylate</strong> 2 (1 eq.) was combined with K2CO3 (10 eq.), the appropriate (het)aryl boronic acid (1.5 eq.) and Pd(PPh3)4 (5 mol%) in a two-neck round bottom flask. The flask was connected to a condenser and purged with nitrogen. A 4:1 mixture of anhydrous toluene: MeOH (60 mL) was added via syringe and the reaction mixture was heated at reflux for 0.5-18 h. The mixture was allowed to cool to room temperature and filtered through Celite (10 x 3 cm, eluting with 3 x 20 mL EtOAc). The filtrate was evaporated to dryness and the residue purified by silica gel flash column chromatography using EtOAc/pet spirit.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29

26
[ 110-00-9 ]
[ 25015-63-8 ]
[ 374790-93-9 ]
[ 248924-59-6 ]
2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]
2,4-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%Spectr.; 11%Spectr.; 5%Spectr.; 5%Spectr.	With Fe(1,2-bis(dimethylphosphino)ethane)2Cl2; sodium 2-ethylhexanoic acid; In tetrahydrofuran; at 60℃; for 48h;Inert atmosphere; Schlenk technique; Irradiation; Glovebox;	General procedure: In an argon-filled glovebox, dmpe2FeCl2 1 (8.6 mg, 0.02 mmol), sodium 2-ethylhexanoate (6.6 mg,0.04 mmol), HBpin (87 L, 0.6 mmol), substrate (0.5 mmol), and THF (1 mL) were added to a 1.7 mL sample vial and shaken to ensure full dissolution. The vial was placed under blue light radiation for 48 h and then allowed to cool to room temperature. Yields determined by 1H-NMR spectroscopy ofthe crude reaction mixtures using 1,3,5-trimethoxybenzene as an internal standard [0.5 mL; standard solution = 1,3,5-trimethoxybenzene (0.336 g, 2.0 mmol) in diethyl ether (10 mL)]. Product ratios were determined by 1H-NMR spectroscopy of the crude reaction mixtures.

Reference： [1]Molecules,2020,vol. 25

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[ CAS No. 248924-59-6 ]

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[ 248924-59-6 ] Synthesis Path-Upstream 1~4

[ 248924-59-6 ] Synthesis Path-Downstream 1~26

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Organoboron

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Furans

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