dimethyl-1H-1,2,4-triazol-3-amine → 5-(1,5-Dimethyl-1H-[1,2,4]triazol-3-ylamino)-2-(4-methyl-imidazol-1-yl)-benzonitrile

HRID 2063626Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[CH3:16][N:17]1[C:21]([CH3:22])=[N:20][C:19]([NH2:23])=[N:18]1.[O-]C1C=CC=CC=1.[Na+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.O>[CH3:16][N:17]1[C:21]([CH3:22])=[N:20][C:19]([NH:23][C:2]2[CH:3]=[CH:4][C:5]([N:10]3[CH:14]=[C:13]([CH3:15])[N:12]=[CH:11]3)=[C:6]([CH:9]=2)[C:7]#[N:8])=[N:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile (50 mg, 0.19 mmol), 1,5-dimethyl-1H-1,2,4-triazol-3-amine (45 mg, 0.40 mmol), sodium phenoxide (66 mg, 0.57 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (3 mg, 0.003 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene=Xanthphos (7 mg, 0.012 mmol) in 5 ml of dioxane was heated to 80° C. under argon for 2 hours. The mixture was diluted with water, extracted with ethyl acetate and the product purified by chromatography on silica gel using dichloromethane/methanol 9:1 v/v as an eluent. The title compound was obtained as a yellowish solid (6 mg, 11%). MS ISN (m/e): 292.3 (100) [(M−H)−].

Workup

extractionextracted with ethyl acetate
customthe product purified by chromatography on silica gel

Sources & evidence

ORD record: ord-10d9c8c55b70436581344f4ee7a09578
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288403B2

Reaction notes

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