5-tert-butyl-6-nitro-1H-indole → HCID 57470208, 화합물

HRID 73954노트

반응식

HRID 73954 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[N+:14]([O-])=O)[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2]>CO.[Ni]>[C:1]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[NH2:14])[NH:10][CH:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 574702075-tert-butyl-6-nitro-1H-indole

생성물 1

HCID 57470208HCID 57470208, 화합물수율 87.2%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

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온도
30 °C

실험 절차

Raney Ni (3 g) was added to 5-tert-butyl-6-nitro-1H-indole (14.7 g, 67 mmol) in methanol (100 mL). The mixture was stirred under hydrogen (1 atm) at 30° C. for 3 h. The catalyst was filtered off. The filtrate was dried over Na2SO4 and concentrated. The crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether) to give 5-tert-butyl-1H-indol-6-ylamine (B-24) as a gray solid (11 g, 87%). 1H NMR (300 MHz, DMSO-d6) δ 10.3 (br s, 1H), 7.2 (s, 1H), 6.9 (m, 1H), 6.6 (s, 1H), 6.1 (m, 1H), 4.4 (br s, 2H), 1.3 (s, 9H).

후처리

  1. filtrationThe catalyst was filtered off
  2. dry with materialThe filtrate was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude dark brown viscous oil was purified by column chromatography (10-20% EtOAc/petroleum ether)

출처 및 근거

ORD 기록
ord-2e778528986a4dd0a928b8a36038a39a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829204B2

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