2-isopropyl-5-nitro-1H-indole → HCID 59129404、化合物

HRID 1403942ノート

反応式

HRID 1403942 の反応式
[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]

参加物

4

反応物 1

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

生成物 1

HCID 59129404HCID 59129404、化合物収率 41%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 887Methanol溶媒

実験手順

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, 1H), 7.10 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.4 Hz, 1H), 6.58 (dd, J=2.4, 8.8 Hz, 1H), 6.07 (t, J=1.2 Hz, 1H), 3.55 (br s, 2H), 3.06-2.99 (m, 1H), 1.33 (d, J=7.2 Hz, 6H); MS (ESI) m/e (M+H+) 175.4.

後処理

  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)

出典と根拠

ORDレコード
ord-8b6e2c3aa2974b669b918616e124241a
出典データセット
uspto-grants-2014_12
特許番号
US08912199B2

反応ノート

読み込み中…