Ammonia → 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

HRID 71192Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([CH3:13])=[N:9]2)=[C:4]([F:14])[CH:3]=1.[C:15](OCC)(=O)C.O.[NH3:22]>CN(C)C(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Zn].[C-]#N.[Zn+2].[C-]#N>[F:14][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1)[C:15]#[N:22]

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of 1-(4-bromo-2-fluorophenyl)-3-methyl-1H-1,2,4-triazole (5.5 g), tris(dibenzylideneacetone)dipalladium(0) (393 mg), 1,1′-bis(diphenylphosphino)ferrocene (476 mg) and zinc powder (169 mg) in N,N-dimethylacetamide (20 mL) was added zinc(II) cyanide (1.5 g) at room temperature, and the mixture was stirred at 120° C. for 1 hr. To the reaction mixture were added ethyl acetate, water and aqueous ammonia. The organic layer was separated, washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (3.84 g).

Workup

customThe organic layer was separated
washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-ae4dd0e91d934f15bd5acda15b849c4d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

Loading…