Methanol → Gsk-2881078

HRID 1851119ノート

反応式

HRID 1851119 の反応式
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]

参加物

5

反応物 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86709175HCID 86709175、化合物

生成物 1

HCID 86709174Gsk-2881078

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ad2bc5fb650e41159de949603ccdbdad
出典データセット
uspto-grants-2015_02
特許番号
US08957104B2

反応ノート

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