Sodium Sulfite → (1-(5-Bromopyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone

HRID 630487Notes

Reaction equation

HRID 630487 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[Br:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[O:29])[CH:26]=3)[C:21]([S:36][CH3:37])=[CH:20]2)=[N:17][CH:18]=1.S([O-])([O-])=O.[Na+].[Na+]>ClCCl>[Br:12][C:13]1[CH:18]=[N:17][C:16]([N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:28]([N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)=[O:29])[CH:26]=3)[C:21]([S:36]([CH3:37])=[O:6])=[CH:20]2)=[N:15][CH:14]=1

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 118666053(1-(5-Bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone

Product 1

HCID 118666026(1-(5-Bromopyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(morpholino)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

m-Chloroperoxybenzoic acid (77%, 2.10 g, 9.42 mmol) in dichloromethane (20 mL) was added at 0° C. to a solution of (1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino) methanone (4.8 g, 11.08 mmol) in dry dichloromethane (300 mL). The mixture was stirred at room temperature for 3 h and then poured onto saturated sodium sulfite solution. The organic layer was separated after stirring for 15 min and washed with saturated sodium hydrogen carbonate solution and brine. The organic phase was dried over sodium sulfate and concentrated and the remnant was purified by flash column chromatography [dichloromethane with 2.5% methanol]. White solid. Yield: 3.2 g

Workup

  1. customThe organic layer was separated
  2. stirringafter stirring for 15 min
  3. washwashed with saturated sodium hydrogen carbonate solution and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated
  6. customthe remnant was purified by flash column chromatography [dichloromethane with 2.5% methanol]

Sources & evidence

ORD record
ord-f6c741fd59ae4d7ba245ab7251500e3e
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

Loading…