Methanol → Gsk-2881078

HRID 1851119노트

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HRID 1851119 반응식
CS[CH2:3][C@H:4]([N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:5].O[O:22][S:23]([O-:25])=O.[K+].[CH3:27]O>O>[CH3:27][S:23]([CH2:5][C@H:4]([N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:19])([F:18])[F:20])[C:11]([C:15]#[N:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:3])(=[O:25])=[O:22]

참가 물질

5

반응물 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86709175HCID 86709175, 화합물

생성물 1

HCID 86709174Gsk-2881078

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

To an ice-cold solution of (R)-1-(1-(methylthio)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.560 g, 1.88 mmol) in MeOH (10 mL) was added a solution of Oxone (4.04 g, 6.57 mmol) in water (10 mL). After 50 min, the reaction mixture was diluted with water (30 mL) and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was chromatographed over silica gel using 100% CH2Cl2 to give (R)-1-(1-(methylsulfonyl)propan-2-yl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile as a white foam that was crystallized from CH2Cl2/hexanes to afford a white solid (0.508 g, 79% yield): 1H NMR (400 MHz, DMSO-d6) δ 8.17 (d, J=8.6 Hz, 1H), 8.12 (d, J=3.5 Hz, 1H), 7.81 (d, J=8.5 Hz, 1H), 6.87-6.84 (m, 1H), 5.43-5.35 (m, 1H), 4.01 (dd, J=14.8, 8.6 Hz, 1H), 3.83 (dd, J=14.8, 4.9 Hz, 1H), 2.77 (s, 3H), 1.59 (d, J=6.8 Hz, 3H); MS (ESI): m/z 331 (M+H).

후처리

  1. extractionextracted with EtOAc (50 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed over silica gel using 100% CH2Cl2

출처 및 근거

ORD 기록
ord-ad2bc5fb650e41159de949603ccdbdad
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957104B2

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