Triethylsilane → 1-benzyl-2-(triethylsilyl)-1H-indole

HRID 627460

반응식

HRID 627460 반응식
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[SiH:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25]>O1CCCC1>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[Si:23]([CH2:28][CH3:29])([CH2:26][CH3:27])[CH2:24][CH3:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 12052TriethylsilaneHCID 969131-BenzylindoleHCID 23665647Potassium tert-butoxide

생성물 1

HCID 900959671-benzyl-2-(triethylsilyl)-1H-indole수율 31.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The reaction was conducted according to the General Procedure by heating 1-benzylindole (62 mg, 0.5 mmol, 1 equiv.), KOt-Bu (11 mg, 0.1 mmol, 0.2 equiv) and Et3SiH (239 microliters, 1.5 mmol, 3 equiv.) in 1 mL of tetrahydrofuran for 48 hours at 23° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica using hexanes (isochratic) to obtain 50 mg (31%) of the title compound as a colourless oily solid. 1H NMR (500 MHz, THF-d8) δ 7.56 (ddd, J=7.7, 1.3, 0.7 Hz, 1H), 7.25-7.07 (m, 4H), 7.02 (ddd, J=8.2, 6.9, 1.3 Hz, 1H), 6.98 (ddd, J=7.9, 6.9, 1.1 Hz, 1H), 6.92-6.86 (m, 2H), 6.80 (d, J=0.9 Hz, 1H), 5.52 (s, 2H), 1.06-0.88 (m, 9H), 0.85-0.69 (m, 6H).

후처리

  1. customAfter aqueous work up, the crude reaction mixture
  2. customwas purified by chromatography on silica

출처 및 근거

ORD 기록
ord-0d4db364608c477f81ed0fc5e7145286
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309269B2

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