Triethylamine → Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

HRID 453856노트

반응식

HRID 453856 반응식
Br[CH2:2][C:3]1[N:4]([CH3:17])[C:5]2[C:10]([C:11]=1[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=2.[NH2:18][C:19]1[CH:27]=[C:26]2[C:22]([CH:23]=[CH:24][N:25]2[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1.C(OCC)(=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:25]1[C:26]2[C:22](=[CH:21][CH:20]=[C:19]([NH:18][CH2:2][C:3]3[N:4]([CH3:17])[C:5]4[C:10]([C:11]=3[C:12]([O:14][CH3:15])=[O:13])=[C:9]([Cl:16])[CH:8]=[CH:7][CH:6]=4)[CH:27]=2)[CH:23]=[CH:24]1)([CH3:35])([CH3:33])[CH3:34]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 59473728tert-butyl 2-(6-amino-1H-indol-1-yl)acetate2회HCID 59473756Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate

생성물 1

HCID 68427131Methyl 2-((1-(2-tert-butoxy-2-oxoethyl)-1H-indol-6-ylamino)methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate수율 55%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

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온도
25 °C

실험 절차

Methyl 2-(bromo-methyl)-4-chloro-1-methyl-1H-indole-3-carboxylate (1.10 mmol, 1.0 equiv.) and tert-butyl 2-(6-amino-1H-indol-1-yl)acetate (intermediate A) (1.10 mmol, 1.0 equiv.) were dissolved in benzene (5 ml) and triethylamine (1.3 mmol, 1.2 equiv.) and refluxed for 16 h. The reaction mixture was cooled to 25° C., diluted with ethyl acetate and washed with water and sat. NaCl solution. Drying over Na2SO4 was then carried out, followed by concentration under reduced pressure. The crude product was purified by column chromatography (40% ethyl acetate in hexane). Yield: 55%

후처리

  1. washwashed with water and sat. NaCl solution
  2. dry with materialDrying over Na2SO4
  3. concentrationfollowed by concentration under reduced pressure
  4. customThe crude product was purified by column chromatography (40% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-f1c1fff7fd3743aebba8912a66a5d9a6
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492559B2

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