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

HRID 1785970Notes

Reaction equation

HRID 1785970 reaction equation
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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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

Workup

  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

Sources & evidence

ORD record
ord-ac18ee8682d04f73b3a43febaf0c43ce
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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