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

HRID 630460Notes

Reaction equation

HRID 630460 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

A solution of m-chloroperoxybenzoic acid (77%, 2.10 g, 9.42 mmol) in dichloromethane (20 mL) was added at 0° C. to (1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indol-6-yl)(morpholino)methanone (0.18 g, 0.25 mmol) in dry dichloromethane (300 mL). The mixture was stirred at room temperature for 4 h and then poured onto saturated sodium sulfite solution (20 mL). The organic layer was separated after stirring for 15 min and washed with saturated sodium hydrogen carbonate solution and brine. The organic phase was then dried over sodium sulphate and concentrated. The residue was purified by flash column chromatography [methanol/dichloromethane=1:40]. 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 then dried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by flash column chromatography [methanol/dichloromethane=1:40]

Sources & evidence

ORD record
ord-0b9a6e14afc84cf2ae1af6c870a18db2
Source dataset
uspto-grants-2016_04
Patent number
US09315490B2

Reaction notes

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