Water → HCID 11848542, compound

HRID 1671609Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[N:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[CH2:19][CH2:18]2)=[O:16])[C:5](=[O:13])[N:6]([CH2:8][C:9]([F:12])([F:11])[F:10])[CH:7]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC>[O:13]=[C:5]1[C:4]([CH2:14][C:15]([N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[N:27][CH:28]=[CH:29][CH:30]=4)[NH:25][C:24]3=[O:32])[CH2:19][CH2:18]2)=[O:16])=[CH:3][C:2]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:7][N:6]1[CH2:8][C:9]([F:12])([F:11])[F:10]

Participants

Conditions

Temperature: 85 °C

Procedure

1,1′-Bis(diphenylphospino)ferrocene palladium(II)dichloride dichloromethane complex (5 mg, 0.006 mmol) was added to a solution of 1-(1-{[5-bromo-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydropyridin-3-yl]acetyl}piperidin-4-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (50 mg, 0.097 mmol), phenyl boronic acid (14 mg, 0.117 mmol), and potassium phosphate (45 mg, 0.214 mmol), in DME (2 mL) and heated to 85° C. After 24 h, water was added and the mixture was extracted with ethyl acetate (3×). The organic layers were dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography [99%-85% dichloromethane/methanol] gave the title compound (25 mg). MS 512.1861 (M+1).

Workup

extractionthe mixture was extracted with ethyl acetate (3×)
dry with materialThe organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by silica gel chromatography [99%-85% dichloromethane/methanol]

Sources & evidence

ORD record: ord-31098f0d2c324519b24da8be30f91999
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994325B2

Reaction notes

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