m-Chloroperbenzoic acid → 1-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-N-(2-(methylamino)-2-oxoethyl)-3-(methylsulfinyl)-1H-indole-6-carboxamide

HRID 630536Notes

Reaction equation

HRID 630536 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([N:26]([CH3:32])[CH2:27][C:28]([NH:30][CH3:31])=[O:29])=[O:25])[CH:22]=3)[C:17]([S:33][CH3:34])=[CH:16]2)=[N:13][CH:14]=1.ClC1C=C(C=CC=1)C(OO)=[O:40]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][C:12]([N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([C:24]([N:26]([CH3:32])[CH2:27][C:28]([NH:30][CH3:31])=[O:29])=[O:25])[CH:22]=3)[C:17]([S:33]([CH3:34])=[O:40])=[CH:16]2)=[N:13][CH:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1186767851-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-N-(2-(methylamino)-2-oxoethyl)-3-(methylthio)-1H-indole-6-carboxamide

Product 1

HCID 1186661411-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-N-methyl-N-(2-(methylamino)-2-oxoethyl)-3-(methylsulfinyl)-1H-indole-6-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxidation of 304d) (0.1 g, 0.209 mmol) with m-chloroperoxybenzoic acid (77%, 0.038 g, 0.167 mmol) in dichloromethane (10 mL). White solid. Yield: 0.065 g (63% of theory)

Sources & evidence

ORD record
ord-e2af40944b954cedb9a8bdb52e83b83e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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