t-Butyl 5-nitroindole-2-carboxylate → Tert-butyl 5-amino-1H-indole-2-carboxylate

HRID 1356584노트

반응식

HRID 1356584 반응식
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2)([O-])=O>[Pd].CO.C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:7]2

참가 물질

4

반응물 1

HCID 10801431t-Butyl 5-nitroindole-2-carboxylate

생성물 1

HCID 10633339Tert-butyl 5-amino-1H-indole-2-carboxylate수율 97%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A 500 mL Par hydrogenation bottle was charged with compound 10 (5.80 g, 22.14 mmol), 10% Pd/C (0.6 g) and methanol/THF (150 mL, 1:4 v/v), and purged with hydrogen. The reaction mixture was shaken with 50 psi H2 over night. The catalyst was removed by filtration and the solvent was evaporated to give 4.98 g (97% yield) of the title compound 11 as brown solid. 1H NMR (DMSO), 11.42 (s, 1H), 7.18 (d, 1H, J=8.3 Hz), 6.83 (s, 1H), 6.71 (s, 1H), 6.67 (d, 1H, J=8.4 Hz), 1.62 (s, 9H). This product is unstable and therefore it was immediately used in the following step.

후처리

  1. custompurged with hydrogen
  2. customThe catalyst was removed by filtration
  3. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-277453ed96474abcab97a6045c483b4e
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06586618B1

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