HCID 59129336, 화합물 → 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine

HRID 1908446노트

반응식

HRID 1908446 반응식
[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([N+:14]([O-])=O)=[CH:9][CH:8]=3)[CH2:4][CH2:3]1>CCO.[Ni]>[CH3:1][C:2]1([C:5]2[NH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][C:10]([NH2:14])=[CH:9][CH:8]=3)[CH2:4][CH2:3]1

참가 물질

4

반응물 1

HCID 59129336HCID 59129336, 화합물

생성물 1

HCID 591295412-(1-methyl-cyclopropyl)-1H-indol-5-ylamine수율 28.5%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매

실험 절차

To a solution of 2-(1-methylcyclopropyl)-5-nitro-1H-indole (0.70 g, 3.2 mmol) in EtOH (20 mL) was added Raney Nickel (100 mg) under nitrogen atmosphere. The mixture was stirred under hydrogen atmosphere (1 atm) at room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1) to afford 2-(1-methyl-cyclopropyl)-1H-indol-5-ylamine (170 mg, 28%). 1H NMR (400 MHz, CDCl3) δ 7.65 (brs, 1H), 7.08 (d, J=8.4 Hz, 1H), 6.82 (s, 1H), 6.57 (d, J=8.4 Hz, 1H), 6.14 (s, 1H), 3.45 (brs, 2H), 1.47 (s, 3H), 0.82-0.78 (m, 2H), 0.68-0.63 (m, 2H).

후처리

  1. filtrationThe catalyst was filtered off through a celite pad
  2. customthe filtrate was evaporated under vacuum
  3. customThe residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-f5284cd012f047919dae83b33ec7dde6
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598181B2

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