Hydrochloric Acid → HCID 86666500, compound

HRID 1426308Notes

Reaction equation

HRID 1426308 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[C:9]([CH2:17][N:18]([CH3:20])[CH3:19])[CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.CN(C)[CH:23]=[O:24].Cl.C(=O)(O)[O-].[Na+]>C1COCC1.O>[CH3:19][N:18]([CH2:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=1)[CH:23]=[O:24])[CH3:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 594394031-[3-bromo-5-(trifluoromethyl)phenyl]-N,N-dimethylmethanamineHCID 178418339Butyllithium

Product 1

HCID 86666500HCID 86666500, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.5M n-Butyllithium in hexanes (0.47 mL, 1.2 mmol) was added dropwise to a solution of 1-[3-bromo-5-(trifluoromethyl)phenyl]-N,N-dimethylmethanamine (0.30 g, 1.1 mmol, from Step A) in THF (6.0 mL) at −78° C. After stirring at this temperature for 20 minutes, N,N-dimethylformamide (160 μL, 2.1 mmol) was added dropwise. After a total reaction time of 50 minutes at −78° C., the reaction was quenched with 1.0M Hydrogen chloride in water (2.1 mL, 2.1 mmol). After warming to room temperature, the mixture was diluted with more water, treated with saturated sodium bicarbonate to achieve pH 7, then extracted with ethyl acetate (EtOAc). The combined extracts were washed with water (3×), brine, dried over sodium sulfate and concentrated to give a light yellow oil, a 4:1 mixture of the desired together with de-bromination byproduct, which was used without further purification (0.2 g, 60%).

Workup

  1. extractionextracted with ethyl acetate (EtOAc)
  2. washThe combined extracts were washed with water (3×), brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a light yellow oil
  6. additiona 4:1 mixture of the
  7. customwas used without further purification (0.2 g, 60%)

Sources & evidence

ORD record
ord-7ac699470b9e480a8293f3f2301e8ac4
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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