Cesium carbonate → 3-Fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile

HRID 59947

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH3:10])[C:6]=2[CH:11]=1.[NH2:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][C:14]=1[F:21].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[F:21][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][C:13]=1[NH:12][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([CH3:10])[C:6]=2[CH:11]=1)[C:17]#[N:18]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture containing 6-bromo-1-methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol), XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mL) was stirred at 110° C. for approximately 16 h. The mixture was diluted (EtOAc), washed (H2O), dried (Na2SO4) and concentrated to yield the desired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

Workup

washwashed (H2O)
dry with materialdried (Na2SO4)
concentrationconcentrated

Sources & evidence

ORD record: ord-efd2f57049f347bb9455181c6f81fbac
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440929B2

Linked notes

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