Potassium hydroxy sulfite → HCID 73296459, compound

HRID 623756Notes

Reaction equation

HRID 623756 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([CH3:17])[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[C:9]1[C:25]([N:27]1[CH2:32][CH2:31][S:30][CH2:29][CH2:28]1)=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:33]OS([O-])=O.[K+]>CO.O>[CH2:1]([N:8]1[C:12]([C:13]([F:15])([F:16])[F:14])=[C:11]([CH3:17])[C:10]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[C:9]1[C:25]([N:27]1[CH2:28][CH2:29][S:30](=[O:33])[CH2:31][CH2:32]1)=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 86711840HCID 86711840, compound

Product 1

HCID 73296459HCID 73296459, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of (1-benzyl-3-(4-chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl)(thiomorpholino)methanone [for synthesis see SC-26] (131 mg, 0.28 mmol) in MeOH (4 mL) and H2O (1 mL) was added oxone (85 mg, 0.138 mmol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with H2O and extracted with DCM (60 mL). The organic layer was washed with brine, dried (Na2SO4) and purified by flash column chromatography (silica, heptane/EtOAc, 1:1→0:1) to give SC-19 (48 mg, 35%) as a white foam.

Workup

  1. extractionextracted with DCM (60 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. custompurified by flash column chromatography (silica, heptane/EtOAc, 1:1→0:1)
  5. customto give SC-19 (48 mg, 35%) as a white foam

Sources & evidence

ORD record
ord-a7fa878cedf6458f881ee8b9289df0da
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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