Potassium Carbonate → N-[3-Fluoro-4-({1-[(4-methylphenyl)sulfonyl]-3-vinyl-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)phenyl]acetamide

HRID 2192167Notes

Reaction equation

Br[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[CH:14][C:13]=2[F:22])[N:4]([S:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:39](B(OCCCC)OCCCC)=[CH2:40].C(=O)(O)[O-].[Na+]>CN(C=O)C>[F:22][C:13]1[CH:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[CH:16]=[CH:17][C:12]=1[O:11][C:9]1[CH:8]=[CH:7][N:6]=[C:5]2[N:4]([S:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)(=[O:25])=[O:24])[CH:3]=[C:2]([CH:39]=[CH2:40])[C:10]=12

Participants

Conditions

Temperature: 90 °C

Procedure

1.00 g (1.93 mmol) of N-[4-({3-bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}oxy)-3-fluorophenyl]acetamide and 800 mg (5.79 mmol) of potassium carbonate are suspended in DMF (6 ml). The solution is degassed and vented with argon. 79 mg (0.110 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) chloride/methylene dichloride complex and 0.85 ml (3.86 mmol) of di-n-butyl vinylboronate are then added, and the mixture is stirred at 90° C. for 3 hours. After addition of sodium bicarbonate solution, the mixture is extracted three times with dichloromethane. The combined organic phases are concentrated, and the crude product is purified by chromatography on silica gel (mobile phase: dichloromethane/acetone 20:1 to 10:1).

Workup

customThe solution is degassed
extractionthe mixture is extracted three times with dichloromethane
concentrationThe combined organic phases are concentrated
customthe crude product is purified by chromatography on silica gel (mobile phase: dichloromethane/acetone 20:1 to 10:1)

Sources & evidence

ORD record: ord-ae9de4fd261a4b8390626524d1d1a2c2
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329716B2

Reaction notes

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