1-(3-Bromo-4-fluorophenyl)ethanol → Methyl 1-(5-(2-fluoro-5-(1-hydroxyethyl)phenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

HRID 630528Notes

Reaction equation

HRID 630528 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[C:10]([S:21][CH3:22])=[CH:9]2)=[N:6][CH:7]=1.Br[C:24]1[CH:25]=[C:26]([CH:31]([OH:33])[CH3:32])[CH:27]=[CH:28][C:29]=1[F:30]>>[F:30][C:29]1[CH:28]=[CH:27][C:26]([CH:31]([OH:33])[CH3:32])=[CH:25][C:24]=1[C:2]1[CH:3]=[N:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([O:19][CH3:20])=[O:18])[CH:15]=3)[C:10]([S:21][CH3:22])=[CH:9]2)=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 207853061-(3-Bromo-4-fluorophenyl)ethanolHCID 118666039Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Product 1

HCID 118666176Methyl 1-(5-(2-fluoro-5-(1-hydroxyethyl)phenyl)pyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate

Procedure

Synthesized from methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate (1.0 g, 2.65 mmol) and 1-(3-bromo-4-fluorophenyl)ethanol (0.87 g, 3.98 mmol) analogously to the experimental procedure 289a). Yellow solid. Yield: 1.0 g (89% of theory)

Sources & evidence

ORD record
ord-95fa63f4d9e9445eb438fec3bcca8033
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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