Acetic Acid → N-(5-amino-2,4-difluorophenyl)-3-(2-cyanopropan-2-yl)benzamide

HRID 1184883Notes

Reaction equation

[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][CH:25]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([N+:18]([O-])=O)[C:15]([F:21])=[CH:14][C:13]=1[F:22])=[O:10])([CH3:5])[CH3:4])#[N:2].C(O)(=O)C.C(O)C.C(#N)C>C1COCC1.[Zn]>[NH2:18][C:16]1[C:15]([F:21])=[CH:14][C:13]([F:22])=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:23]=[CH:24][CH:25]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=1

Participants

Conditions

Temperature: -5 °C

Procedure

To a mixture of 3-(2-cyanopropan-2-yl)-N-(2,4-difluoro-5-nitrophenyl)benzamide 72 (155 mg, 0.449 mmol) and zinc (440 mg, 6.73 mmol) in THF (5 mL) at −5° C., acetic acid (0.514 mL, 539 mg, 8.98 mmol) was added. The reaction was stirred 30 min at −5° C. and 1 h at rt. Ethanol and acetonitrile were added and filtrated. The filtrate was diluted with CH2Cl2 and washed with saturated NaHCO3 solution to give N-(5-amino-2,4-difluorophenyl)-3-(2-cyanopropan-2-yl)benzamide 73 (100 mg, 70%). (m/z)=316 (M+H)+.

Workup

filtrationfiltrated
additionThe filtrate was diluted with CH2Cl2
washwashed with saturated NaHCO3 solution

Sources & evidence

ORD record: ord-fe50019c4a89474b8a3bf92195f65ae4
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669256B2

Reaction notes

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