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

반응식

HRID 562013 반응식
[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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-5e3c8c72eef24a21aaa49d1c7556cc62
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063071B2

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