4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-((E)-propenyl)benzonitrile → 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile

HRID 923253노트

반응식

HRID 923253 반응식
[CH:1]1[N:5]=[CH:4][N:3]2[CH:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3/[CH:17]=[CH:18]/[CH3:19])[CH2:7][CH2:8][C:2]=12>[Pd].CCO>[CH:1]1[N:5]=[CH:4][N:3]2[CH:6]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=3[CH2:17][CH2:18][CH3:19])[CH2:7][CH2:8][C:2]=12

참가 물질

4

반응물 1

HCID 588271824-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-((E)-propenyl)benzonitrile

생성물 1

HCID 588270944-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A suspension of 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-((E)-propenyl)benzonitrile (0.150 g, 0.602 mmol), 20% (w/w) palladium on carbon (0.040 g), THE (15 mL), and EtOH (15 mL) is stirred under an atmosphere of hydrogen (1 atm) for 60 h. The suspension is the filtered and the filtrate concentrated. The residue is then purified by flash chromatography (Hexane/EtOAc, and then 10% MeOH/EtOAc) to give 4-(6,7-Dihydro-5H-pyrrolo[1,2-c]imidazol-5-yl)-3-(n-propyl)benzonitrile as a white solid. MS (ESI) m/z 252.1 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.04 (t, J=7.3 Hz, 3H), 1.63-1.77 (m, 2H), 2.33-2.45 (m, 1H), 2.62-2.80 (m, 2H), 2.92 (app t, J=7.1 Hz, 2H), 3.04-3.19 (m, 1H), 5.58 (dd, J=7.8, 5.6 Hz, 1H), 6.73 (d, J=8.1 Hz, 1H), 6.81 (s, 1H), 7.25 (s, 1H), 7.41 (d, J=8.1 Hz, 1H), 7.51 (s, 1H).

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated
  3. customThe residue is then purified by flash chromatography (Hexane/EtOAc

출처 및 근거

ORD 기록
ord-3872eb546e8047d38a8a6c52256c0666
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278969B2

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