Dichloromethane → 3-(4,5-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

HRID 1867234Notes

Reaction equation

HRID 1867234 reaction equation
C(N(S(F)(F)[F:7])CC)C.C(Cl)Cl.[F:13][C:14]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:15]=1[CH:16](O)[C:17]([CH3:35])([CH3:34])[N:18]=[C:19]2[C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[CH:29][CH:28]=2>O>[F:7][CH:16]1[C:15]2[C:20](=[CH:21][CH:22]=[CH:23][C:14]=2[F:13])[C:19]([C:24]2[CH:25]=[N:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:18][C:17]1([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 231608883-(5-Fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline

Product 1

HCID 231608243-(4,5-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diethylaminosulphur trifluoride (76 mg) was added to an methylene chloride (20 mL) solution of 3-(5-fluoro-4-hydroxy-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline (50 mg, 0.16 mmol), followed by stirring for 1 hour under ice cooling, pouring water, extracting with ethyl acetate, and applying the resulting residue to chromatography to obtain 45 mg (yield 90%) of the target compound.

Workup

  1. extractionextracting with ethyl acetate

Sources & evidence

ORD record
ord-8fa5292edb554aa7917d47d7aed467b7
Source dataset
uspto-grants-2009_12
Patent number
US07632783B2

Reaction notes

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