Boron tribromide → N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

HRID 1785970노트

반응식

HRID 1785970 반응식
FC1C=CC(C(Cl)=O)=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1.B(Br)(Br)Br>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:14][CH:13]=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([N:18]([C@H:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[N:25]([C:32](=[O:41])[C:33]3[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=3)[C@@H:24]([CH3:42])[CH2:23]2)[C:19](=[O:21])[CH3:20])=[CH:16][CH:17]=1

참가 물질

6

반응물 3

HCID 25134Boron tribromideHCID 678794-Fluorobenzoyl chlorideHCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

생성물 2

HCID 10343669N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-methoxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamideHCID 58859774N-(4-chlorophenyl)-N-[(2S,4R)-1-(4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2S,4R)-N-(4-Chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was prepared following general procedure G, substituting 4-methoxybenzoyl chloride for 4-fluorobenzoyl chloride. (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-methoxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide was dissolved in dichloromethane and a solution of BBr3 (1.0 M in dichloromethane, 10 mL) was added; the reaction was allowed to stir at room temperature for until no starting material remained. The reaction was washed with sat NaHCO3 carefully and brine. The organics were dried over MgSO4, filtered and concentrated down. The residue was purified by Biotage flash chromatography using 100% EtOAc to give (2S,4R)-N-(4-chloro-phenyl)-N-[1-(4-hydroxy-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide

후처리

  1. washThe reaction was washed with sat NaHCO3 carefully
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated down
  5. customThe residue was purified by Biotage flash chromatography

출처 및 근거

ORD 기록
ord-ac18ee8682d04f73b3a43febaf0c43ce
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504508B2

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