2-(Trifluoromethyl)benzoic acid → HCID 58792452, compound

HRID 1359944Notes

Reaction equation

HRID 1359944 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.[CH3:14][C:15]([CH3:26])([CH3:25])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH2:24].C(N(CC)C(C)C)(C)C.C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(#N)C.C(OCC)(=O)C.O>[CH3:14][C:15]([CH3:26])([CH3:25])[C:16]#[C:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[CH:11][C:3]=1[C:2]([F:1])([F:13])[F:12]

Participants

7

Reactant 4

HCID 98992-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 2733179PyBroPHCID 140666562-(3,3-Dimethylbut-1-yn-1-yl)aniline

Product 1

HCID 58792452HCID 58792452, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 22728543Water ethylacetateSolvent

Procedure

190 mg (1.0 mmol) of 2-trifluoromethylbenzoic acid, 178 mg (0.83 mmol) of 2-(3,3-dimethyl-but-1-ynyl)phenylamine, 215 mg (1.67 mmol) of N,N-diisopropylethylamine and 583 mg (1.25 mmol) of PyBrOP in 8 ml of acetonitrile were stirred at room temperature for 4 days. 10 ml of ethyl acetate/water 1:1 were added to the mixture and the organic phase was separated off and washed with 10 ml of saturated ammonium chloride solution and subsequently with 10 ml of water. Separation, concentration and drying of the organic phase gave 950 mg of crude product. Column-chromatographic purification on silica gel 60 (petroleum ether/ethyl acetate 10:1→ethyl acetate) gave 110 mg of N-[2-(3,3-dimethylbut-1-ynyl)phenyl]-2-trifluoromethylbenzamide [logP (pH 2.3)=4.55].

Workup

  1. customthe organic phase was separated off
  2. washwashed with 10 ml of saturated ammonium chloride solution and subsequently with 10 ml of water
  3. customSeparation, concentration
  4. customdrying of the organic phase
  5. customgave 950 mg of crude product
  6. customColumn-chromatographic purification on silica gel 60 (petroleum ether/ethyl acetate 10:1→ethyl acetate)

Sources & evidence

ORD record
ord-bac27973fdab406487443dc0bc1a1514
Source dataset
uspto-grants-2011_02
Patent number
US07879760B2

Reaction notes

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