Carbon tetrabromide → 7-(3-bromopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162929Notes

Reaction equation

HRID 1162929 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.OC[CH2:27][CH2:28][NH:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]([F:50])([F:49])[F:48])[NH:36][C:37]2=[O:40])=[CH:32][CH:31]=1>C(Cl)Cl>[Br:24][CH2:20][CH2:27][CH2:28][NH:29][C:30]1[CH:39]=[C:38]2[C:33]([CH:34]=[C:35]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[C:47]([F:50])([F:48])[F:49])[NH:36][C:37]2=[O:40])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 231567767-(3-hydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Product 1

HCID 575581777-(3-bromopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (940 mg, 3.59 mmol) and carbon tetrabromide (1.19 g, 3.59 mmol) were added to a methylene chloride solution (10 ml) that contained the 7-(3-hydroxypropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (500 mg, 1.38 mmol) obtained in step B of Example 1-49. The obtained mixture was stirred at a room temperature for 3 hours. The reaction solvent was distilled away, and the obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2 to 1:1), so as to obtain 7-(3-bromopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (245 mg, 42%).

Workup

  1. distillationThe reaction solvent was distilled away
  2. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2 to 1:1)

Sources & evidence

ORD record
ord-bdedfcac7c9047b0932b0e0cf602dcfa
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

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