2-isopropyl-5-nitro-1H-indole → HCID 59129404, 화합물

HRID 1964322노트

반응식

HRID 1964322 반응식
[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([N+:13]([O-])=O)=[CH:8][CH:7]=2)([CH3:3])[CH3:2]>[Ni].CO>[CH:1]([C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([NH2:13])=[CH:8][CH:7]=2)([CH3:3])[CH3:2]

참가 물질

4

반응물 1

HCID 107268712-isopropyl-5-nitro-1H-indole

생성물 1

HCID 59129404HCID 59129404, 화합물수율 41%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

A suspension of 2-isopropyl-5-nitro-1H-indole (100 mg, 0.49 mmol) and Raney Nickel (10 mg) in MeOH (10 mL) was hydrogenated under hydrogen (1 atm) at the room temperature overnight. The catalyst was filtered off through a celite pad and the filtrate was evaporated under vacuum to give a residue, which was purified by column (petroleum ether/ethyl acetate=5/1) to give 2-isopropyl-1H-indol-5-amine (35 mg, 41%). 1H NMR (400 MHz, CDCl3) δ 7.69 (br s, 1 H), 7.10 (d, J=8.4 Hz, 1 H), 6.86 (d, J=2.4 Hz, 1 H), 6.58 (dd, J=2.4, 8.8 Hz, 1 H), 6.07 (t, J=1.2 Hz, 1 H), 3.55 (br s, 2 H), 3.06-2.99 (m, 1 H), 1.33 (d, J=7.2 Hz, 6 H); MS (ESI) m/e (M+H+) 175.4.

후처리

  1. customwas hydrogenated under hydrogen (1 atm) at the room temperature overnight
  2. filtrationThe catalyst was filtered off through a celite pad
  3. customthe filtrate was evaporated under vacuum
  4. customto give a residue, which
  5. customwas purified by column (petroleum ether/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-554289cf95e34d5383301e953bc21d92
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415387B2

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