Potassium Carbonate → N-(2-Amino-2-oxoethyl)-1-(5-(2-fluoro-5-methoxyphenyl)pyrimidin-2-yl)-N-methyl-3-(methylsulfinyl)-1H-indole-6-carboxamide

HRID 630521Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[NH2:7][C:8](=[O:33])[CH2:9][N:10]([CH3:32])[C:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17]([S:29]([CH3:31])=[O:30])=[CH:18][N:19]2[C:22]2[N:27]=[CH:26][C:25](Br)=[CH:24][N:23]=2)=[CH:15][CH:14]=1)=[O:12].[F:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][C:36]=1B(O)O>C(O)(CC)(C)C.O>[NH2:7][C:8](=[O:33])[CH2:9][N:10]([CH3:32])[C:11]([C:13]1[CH:21]=[C:20]2[C:16]([C:17]([S:29]([CH3:31])=[O:30])=[CH:18][N:19]2[C:22]2[N:27]=[CH:26][C:25]([C:36]3[CH:37]=[C:38]([O:41][CH3:42])[CH:39]=[CH:40][C:35]=3[F:34])=[CH:24][N:23]=2)=[CH:15][CH:14]=1)=[O:12]

Participants

Conditions

Temperature: 95 °C

Procedure

Potassium carbonate (110 mg, 0.79 mmol) and (Ataphos)2PdCl2 (19 mg, 0.026 mmol) were added under an inert atmosphere to a solution of 279a) (120 mg, 0.26 mmol) and 2-fluoro-5-methoxyphenylboronic acid (91 mg, 0.53 mmol) in tert-amylalcohol (4.0 mL) and water (0.4 mL). The reaction mixture was stirred for 4 h at 95° C., then cooled to ambient temperature and filtered over celite. The filtrate was evaporated to dryness and the residue was purified by flash column chromatography [silica; methanol/dichloromethane=4:96]. White solid. Yield: 35 mg (27% of theory)

Workup

temperaturecooled to ambient temperature
filtrationfiltered over celite
customThe filtrate was evaporated to dryness
customthe residue was purified by flash column chromatography [silica; methanol/dichloromethane=4:96]

Sources & evidence

ORD record: ord-3bb3936b28264c3a8a6f34d68c2622cd
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

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