Borane;tetrahydrofuran → 5-(trifluoromethyl)-1H-indole

HRID 1181848노트

반응식

HRID 1181848 반응식
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]2=O.B.C1COCC1>C1COCC1>[F:15][C:2]([F:1])([F:14])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 123514965-(trifluoromethyl)-2,3-dihydro-1H-indole-2,3-dione

생성물 1

HCID 27630755-(trifluoromethyl)-1H-indole수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4 (6.75 g, 31.38 mmol) in dry THF (200 mL) at 0° C. under nitrogen atmosphere BH3.THF solution (82 mL, 1 M in THF) was added dropwise. The mixture was allowed to warm to room temperature and stirred for 1 h. The reaction was quenched with 6N ice-cold aq. HCl (30 mL), made alkaline (pH 7-8) with 2 N NaOH, saturated with NaCl, extracted with EtOAc, the extracts were dried (MgSO4), concentrated. Purification by chromatoghraphy on silica gel using CH2Cl2 as eluent afforded (3.95 g, 68% yield) as an off white solid. 1H NMR (300 MHz, MeOH-d4): δ 7.87 (m, 1H), 7.51 (dd, 8.5, 0.8 Hz, 1H), 7.47 (d, 8.5 Hz, 1H), 7.37 (d, 3.2 Hz, 1H), 7.34 (dd, 8.5, 1.6 Hz, 1H), 6.57 (dd, 3.2, 0.8 Hz, 1H). MS m/z: 184 (M−1).

후처리

  1. customThe reaction was quenched with 6N ice-cold aq. HCl (30 mL)
  2. extractionsaturated with NaCl, extracted with EtOAc
  3. dry with materialthe extracts were dried (MgSO4)
  4. concentrationconcentrated
  5. customPurification by chromatoghraphy on silica gel
  6. customafforded (3.95 g, 68% yield) as an off white solid

출처 및 근거

ORD 기록
ord-8a231d6f552d4edd902b855680ae7124
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285558B2

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