m-Chloroperbenzoic acid → (S)-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-2-(2-(3,5-difluorophenyl)-1-(2,2,2-trifluoroacetamido)ethyl)pyridine 1-oxide

HRID 2170396Notes

Reaction equation

HRID 2170396 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:17]([NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH2:18][C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)=[N:13][CH:14]=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:35][S:36]([CH3:39])(=[O:38])=[O:37])=[N:5][N:6]2[CH3:34].C1C=C(Cl)C=C(C(OO)=[O:48])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C@@H:17]([NH:27][C:28](=[O:33])[C:29]([F:32])([F:30])[F:31])[CH2:18][C:19]3[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([F:26])[CH:20]=3)=[N+:13]([O-:48])[CH:14]=[CH:15][CH:16]=2)=[C:7]2[C:3]=1[C:4]([NH:35][S:36]([CH3:39])(=[O:37])=[O:38])=[N:5][N:6]2[CH3:34]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 90281453(S)-N-(1-(3-(4 chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide

Product 1

HCID 90281489(S)-3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)-2-(2-(3,5-difluorophenyl)-1-(2,2,2-trifluoroacetamido)ethyl)pyridine 1-oxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-(1-(3-(4-chloro-1-methyl-3-(methylsulfonamido)-1H-indazol-7-yl)pyridin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2,2,2-trifluoroacetamide (57B, 8.0 g, 13.61 mmol) in DCM (70 mL) was added mCPBA (3.659 g, 16.33 mmol) in 4 portions over a 15 minute period. The reaction mixture was stirred at room temperature for 16 hours. Upon completion, the reaction was quenched with 1M aqueous NaHSO3 and saturated aqueous NaHCO3. The organic layer was collected and the aqueous layer was extracted an additional time with DCM. The combined organic layers were dried over Na2SO4, filtered, concentrated in vacuo, and purified by silica gel column chromatography, eluting with 50-100% EtOAc in hexanes to give the title compound. MS (m/z) 604.10 [M+H]+.

Workup

  1. customUpon completion, the reaction was quenched with 1M aqueous NaHSO3 and saturated aqueous NaHCO3
  2. customThe organic layer was collected
  3. extractionthe aqueous layer was extracted an additional time with DCM
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography
  8. washeluting with 50-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-c2496ac7958b41df807bb388ce802a7e
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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