Diisopropylethylamine → 1-(2-(1-(3,5-Dimethoxyphenyl)ethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

HRID 1910545Notes

Reaction equation

HRID 1910545 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1F)=[O:4].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:25]([NH2:27])[CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:24][O:23][C:21]1[CH:20]=[C:19]([CH:25]([NH:27][C:6]2[CH:7]=[C:8]([F:11])[CH:9]=[CH:10][C:5]=2[C:3](=[O:4])[C:2]([F:14])([F:13])[F:1])[CH3:26])[CH:18]=[C:17]([O:16][CH3:15])[CH:22]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 135102551-(3,5-Dimethoxyphenyl)ethanamineHCID 247268371-(2,4-Difluorophenyl)-2,2,2-trifluoroethanone

Product 1

HCID 587072861-(2-(1-(3,5-Dimethoxyphenyl)ethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanoneYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,2,2-Trifluoro-1-(2,4-difluorophenyl)ethanone (1.0 g, 4.8 mmol), 1-(3,5-dimethoxyphenyl)ethanamine (0.95 g, 5.2 mmol) and N,N-diisopropylethylamine (1.2 g, 9.6 mmol) were stirred at 60° C. in dry acetonitrile (50 mL) for 16 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and purified by silica chromatography in 20% ethyl acetate in hexanes to collect the title compound (600 mg, 34% yield). 1H NMR (400 MHz, CDCl3): δ 9.27 (s, 1H), 7.79 (t, 1H), 6.44 (s, 2H), 6.35 (m, 2H), 6.23 (d, 1H), 4.48 (m, 1H), 3.77 (s, 6H), 1.61 (d, 3H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. custompurified by silica chromatography in 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4b2835aca9334e56bc60a42ae3d1eaa8
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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