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

HRID 1356584

反応式

HRID 1356584 の反応式
[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

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-277453ed96474abcab97a6045c483b4e
出典データセット
uspto-grants-2003_07
特許番号
US06586618B1

関連ノート

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