Potassium vinyltrifluoroborate → HCID 178436594、化合物

HRID 1875173ノート

反応式

HRID 1875173 の反応式
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]

参加物

5

反応物 2

HCID 23679353Potassium vinyltrifluoroborateHCID 178432869HCID 178432869、化合物

生成物 1

HCID 178436594HCID 178436594、化合物収率 61.3%

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  1. washwashed with water
  2. customThe solvent was removed
  3. customthe crude material was purified via silica gel chromatography

出典と根拠

ORDレコード
ord-6e2ced31b4c5496f942979d6ada4e2eb
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

読み込み中…