m-Chloroperbenzoic acid → (1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

HRID 630550Notes

Reaction equation

HRID 630550 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH:12]1([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]3[CH:22]=[N:23][C:24]([N:27]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([C:36]([N:38]6[CH2:42][CH2:41][CH2:40][CH2:39]6)=[O:37])[CH:34]=5)[C:29]([S:43][CH3:44])=[CH:28]4)=[N:25][CH:26]=3)[CH:16]=2)[CH2:14][CH2:13]1>ClCCl>[CH:12]1([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([C:21]3[CH:26]=[N:25][C:24]([N:27]4[C:35]5[C:30](=[CH:31][CH:32]=[C:33]([C:36]([N:38]6[CH2:42][CH2:41][CH2:40][CH2:39]6)=[O:37])[CH:34]=5)[C:29]([S:43]([CH3:44])=[O:6])=[CH:28]4)=[N:23][CH:22]=3)[CH:16]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 118676890(1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 118671914(1-(5-(4-Cyclopropylpyridin-2-yl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperoxybenzoic acid (77%, 79 mg, 0.35 mmol) was added to an ice cooled solution of 341b) (0.2 g, 0.43 mmol) in dichloromethane (30 mL). The mixture was stirred at room temperature for 1 h and then diluted with dichloromethane (25 mL). The organic phase was washed successively with saturated sodium hydrogen solution (2×15 mL) and brine (1×15 mL), dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography [silica; dichloromethane with 0-2% methanol]. White solid. Yield: 0.08 g (39% of theory)

Workup

  1. washThe organic phase was washed successively with saturated sodium hydrogen solution (2×15 mL) and brine (1×15 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by flash column chromatography [silica; dichloromethane with 0-2% methanol]

Sources & evidence

ORD record
ord-0986915ef617494fa683a53bb695e52e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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