Trifluoroacetic acid → 3-{[3-(Aminomethyl)-6-(difluoromethyl)-2-fluorophenyl]oxy}-5-chlorobenzonitrile

HRID 1875104Notes

Reaction equation

HRID 1875104 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:29])=[C:13]([CH2:20][NH:21]C(=O)OC(C)(C)C)[CH:14]=[CH:15][C:16]=2[CH:17]([F:19])[F:18])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:21][CH2:20][C:13]1[C:12]([F:29])=[C:11]([O:10][C:4]2[CH:5]=[C:6]([CH:7]=[C:2]([Cl:1])[CH:3]=2)[C:8]#[N:9])[C:16]([CH:17]([F:19])[F:18])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867616531,1-Dimethylethyl {[3-[(3-chloro-5-cyanophenyl)oxy]-4-(difluoromethyl)-2-fluorophenyl]methyl}carbamate

Product 1

HCID 684803913-{[3-(Aminomethyl)-6-(difluoromethyl)-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1,1-dimethylethyl {[3-[(3-chloro-5-cyanophenyl)oxy]-4-(difluoromethyl)-2-fluorophenyl]methyl}carbamate (0.152 g, 0.356 mmol) and TFA (1.372 ml, 17.81 mmol) in dichloromethane (10 ml) was stirred for 16 h at RT under an atmosphere of nitrogen. The solution was concentrated under vacuum to give the title compound as an orange oil that was used without further purification. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.40-7.52 (m, 2H), 7.31 (s, 1H), 7.23-7.26 (m, 1H), 6.89 (s, 1H), 6.74 (t, 1H), 4.19 (br. s., 2H).

Workup

  1. concentrationThe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-01af6f8aff2244a7bfa9836b5b2c51ce
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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