Potassium vinyltrifluoroborate → HCID 178436594, compound

HRID 1875173Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([F:29])=[C:13]([CH2:18][NH:19][C:20]([C:22]3[NH:26][C:25]([CH3:27])=[N:24][C:23]=3[Cl:28])=[O:21])[CH:14]=[CH:15][C:16]=2[Cl:17])[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.[CH:30]([B-](F)(F)F)=[CH2:31].[K+]>C(O)CC.CCOC(C)=O>[Cl:28][C:23]1[N:24]=[C:25]([CH3:27])[NH:26][C:22]=1[C:20]([NH:19][CH2:18][C:13]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([O:10][C:4]2[CH:3]=[C:2]([CH:30]=[CH2:31])[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=2)[C:12]=1[F:29])=[O:21]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of N-({3-[(3-bromo-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-2-methyl-1H-imidazole-5-carboxamide (0.480 g, 0.964 mmol), potassium vinyltrifluoroborate (0.194 g, 1.445 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex (0.079 g, 0.096 mmol) in n-propanol (8 ml) was added TEA (0.672 ml, 4.82 mmol) and the reaction mixture was heated at 100° C. for 4 hours. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-cyano-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazol e-5-carboxamide (0.263 g, 0.591 mmol, 61% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05 (t, 1H), 7.77 (s, 1H), 7.47 (d, 1H), 7.40 (br. s., 1H), 7.32 (t, 1H), 7.26 (br. s., 1H), 6.72 (dd, 1H), 6.01 (d, 1H), 5.41 (d, 1H), 4.51 (d, 2H), 2.23 (s, 3H).

Workup

washwashed with water
customThe solvent was removed
customthe crude material was purified via silica gel chromatography

Sources & evidence

ORD record: ord-6e2ced31b4c5496f942979d6ada4e2eb
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304419B2

Reaction notes

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