Potassium vinyltrifluoroborate → HCID 178436594, 화합물

HRID 1875173노트

반응식

HRID 1875173 반응식
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]

참가 물질

5

반응물 2

HCID 23679353Potassium vinyltrifluoroborateHCID 178432869HCID 178432869, 화합물

생성물 1

HCID 178436594HCID 178436594, 화합물수율 61.3%

시약·촉매·용매 2

HCID 10311-Propanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-6e2ced31b4c5496f942979d6ada4e2eb
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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