Hydrochloric Acid → 2-(6-Bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol

HRID 1094657

Reaction equation

HRID 1094657 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][CH:13]=O)[CH:6]=[CH:5]2.[F:15][C:16]([Si](C)(C)C)([F:18])[F:17].[F-].C([NH+](CCCC)CCCC)CCC.Cl.CN(C=[O:42])C>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:42])([CH3:13])[C:16]([F:18])([F:17])[F:15])[CH:6]=[CH:5]2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 11217984Tributylammonium fluorideHCID 86634942HCID 86634942, compound

Product 1

HCID 574581662-(6-Bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol

Procedure

A DMF (5 ml) solution of the 6-bromoquinoline-ethanone (129 mg, 0.52 mmol), (trifluoromethyl)trimethylsilane (220 mg, 1.55 mmol) and tributylammonium fluoride (13.5 mg, 0.052 mmol) was stirred at 100° C. for 2 hours. Then the mixture was cooled to room temperature and added 1M-hydrochloride aqueous solution (2 ml). After 4 hours, the mixture was quenched with saturated sodium bicarbonate aqueous solution, and the product was extracted with ethyl acetate and dried over sodium sulfate. Then, filtration, evaporation, purification through silica gel column chromatography eluting with hexane/ethyl acetate (4:1) furnished the title compound (175 mg, quant.) as a white solid. 1H NMR (300 MHz, CDCl3) ppm 1.81 (3H, s), 6.51 (1H, s), 7.64 (1H, d, J=8.1 Hz), 7.66-7.89 (1H, m), 8.00-8.12 (2H, m), 8.21 (1H, d, J=8.8 Hz). MS (ESI): m/z 320, 322 (M+H)+.

Workup

  1. customthe mixture was quenched with saturated sodium bicarbonate aqueous solution
  2. extractionthe product was extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationThen, filtration, evaporation, purification through silica gel column chromatography
  5. washeluting with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4169104e32c74b31b520149a50878912
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Linked notes

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