Ethanol → Methyl 1-(5-(3-methoxyphenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

HRID 630486Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:9]=[N:10][C:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=3)[C:16]([S:27][CH3:28])=[CH:15]2)=[N:12][CH:13]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.C(O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][O:30][C:31]1[CH:36]=[C:35]([C:8]2[CH:9]=[N:10][C:11]([N:14]3[C:22]4[C:17](=[CH:18][CH:19]=[C:20]([C:23]([O:25][CH3:26])=[O:24])[CH:21]=4)[C:16]([S:27][CH3:28])=[CH:15]3)=[N:12][CH:13]=2)[CH:34]=[CH:33][CH:32]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.20 mmol) and a 2M solution of sodium carbonate (8 mL) were added at room temperature and under an argon atmosphere to methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate (3.0 g, 7.96 mmol) in DME (50 mL). The addition of 3-methoxy phenyl boronic acid (1.53 g, 9.94 mmol) and ethanol (50 mL) followed 10 min later, and the resulting mixture was heated at 90° C. for 5 h. The reaction mixture was then cooled to room temperature and filtered through a pad of celite. The filtrate was concentrated and the residue was purified by flash column chromatography [silica; ethyl acetate/hexane=3:7]. Yellow solid. Yield: 2.6 g (80% of theory)

Workup

temperatureThe reaction mixture was then cooled to room temperature
filtrationfiltered through a pad of celite
concentrationThe filtrate was concentrated
customthe residue was purified by flash column chromatography [silica; ethyl acetate/hexane=3:7]

Sources & evidence

ORD record: ord-87a569e6bb1643e998ce3f2e03f891c4
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315490B2

Reaction notes

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