1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate → tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate

HRID 562013ノート

反応式

HRID 562013 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([Br:26])[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[C:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH:18]=1)=[O:3]>C(O)C.[Pt]=O>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([Br:26])[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH2:17][CH2:18]1)=[O:3]

参加物

4

反応物 1

HCID 596006561,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate

生成物 1

HCID 59600660tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate収率 48.3%

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 702Ethanol溶媒

実験手順

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-3,6-dihydro-1(2H)-pyridinecarboxylate (7.41 g, 17.64 mmol) in ethanol (600 mL), platinum oxide (200 mg, 5%) was added. The reaction mixture was hydrogenated under an atmosphere of H2 for 16 hours. The resulting mixture was filtered through celite and the filtrate was concentrated. The resulting residue was purified by flash column chromatography (Ethyl acetate/hexanes, 1:4 to 2:1 v/v) to give the desired product (3.6 g, 48%).

後処理

  1. filtrationThe resulting mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was purified by flash column chromatography (Ethyl acetate/hexanes, 1:4 to 2:1 v/v)

出典と根拠

ORDレコード
ord-5e3c8c72eef24a21aaa49d1c7556cc62
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

反応ノート

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