3-Methoxyaniline → Ethyl 5-(2-Hydroxy-3-(3-methoxyphenylamino)propyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

HRID 404281노트

반응식

HRID 404281 반응식
[Li+].[Br-].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH2:11])[CH:6]=1.[CH3:12][C:13]1[CH:21]=[CH:20][C:19]2[N:18]([CH2:22][CH:23]3[CH2:25][O:24]3)[C:17]3[CH2:26][CH2:27][N:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:29][C:16]=3[C:15]=2[CH:14]=1>>[OH:24][CH:23]([CH2:25][NH:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([O:4][CH3:3])[CH:6]=1)[CH2:22][N:18]1[C:19]2[CH:20]=[CH:21][C:13]([CH3:12])=[CH:14][C:15]=2[C:16]2[CH2:29][N:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:27][CH2:26][C:17]1=2

참가 물질

4

반응물 3

HCID 108243-MethoxyanilineHCID 82050Lithium BromideHCID 58097199ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate

생성물 1

HCID 46851210Ethyl 5-(2-Hydroxy-3-(3-methoxyphenylamino)propyl)-8-methyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate수율 67.2%

실험 절차

Following a literature procedure (Chakraborti, A. K.; Rudrawar, S.; Kondaskar, A. Eur. J. Org. Chem. 2004, 3597-3600) LiBr (0.001 g, 0.010 mmol) and m-anisidine (0.011 mL, 0.102 mmol) were added to ethyl 8-Methyl-5-(oxiran-2-ylmethyl)-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (0.032 g, 0.102 mmol) and stirred vigorously at ambient temperature overnight. Upon completion the reaction was partitioned between EtOAc/H2O, and the organic layer was concentrated to an orange oil. The crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane) to afford the desired product (30 mg, 67%).

후처리

  1. customUpon completion the reaction was partitioned between EtOAc/H2O
  2. concentrationthe organic layer was concentrated to an orange oil
  3. customThe crude residue was purified by chromatography (SiO2, 0-50% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-49c4f447ed0a4164b04535d119e5a848
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748473B2

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