Water → (E)-methyl 3-(2-methyl-5-(1-methyl-1H-indazol-5-yl)-4-(4-(trifluoromethyl)styryl)phenyl)propanoate

HRID 2194955ノート

反応式

HRID 2194955 の反応式
F[B-](F)(F)F.[CH3:6][O:7][C:8]([CH2:10][CH2:11][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([N+]#N)=[C:14]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([CH3:30])[N:25]=[CH:24]3)[CH:13]=1)=[O:9].O.[F:32][C:33]([F:46])([F:45])[C:34]1[CH:44]=[CH:43][C:37](/[CH:38]=[CH:39]/B(O)O)=[CH:36][CH:35]=1.C(=O)([O-])O.[Na+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C>[CH3:18][C:17]1[CH:16]=[C:15](/[CH:39]=[CH:38]/[C:37]2[CH:36]=[CH:35][C:34]([C:33]([F:32])([F:45])[F:46])=[CH:44][CH:43]=2)[C:14]([C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[N:26]([CH3:30])[N:25]=[CH:24]3)=[CH:13][C:12]=1[CH2:11][CH2:10][C:8]([O:7][CH3:6])=[O:9]

参加物

8

反応物 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 6153620trans-2-[4-(Trifluoromethyl)phenyl]vinylboronic acidHCID 866408694-(2-methoxycarbonylethyl)-5-methyl-2-(1-methyl-1H-indazol-5-yl)benzenediazonium tetrafluoroborate

生成物 1

HCID 66876711(E)-methyl 3-(2-methyl-5-(1-methyl-1H-indazol-5-yl)-4-(4-(trifluoromethyl)styryl)phenyl)propanoate収率 13.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

Example Compound 2-N1-1 (324 mg) was dissolved in a 50% aqueous solution of HBF4 (0.5 ml), and this solution was added dropwise with an aqueous solution (0.5 ml) of sodium nitrite (83 mg) under ice cooling. The reaction mixture was stirred for 30 minutes, and then the precipitates were collected by filtration to obtain 4-(2-methoxycarbonylethyl)-5-methyl-2-(1-methyl-1H-indazol-5-yl)benzene diazonium tetrafluoroborate (Intermediate 16, yield: 200 mg). A solution of this Intermediate 16 (200 mg) in 1,4-dioxane (1 ml) was successively added with water (1 ml), (E)-4-(trifluoromethyl)styrylboronic acid (200 mg, Ald), and Pd(OAc)2 (20 mg, Ald), and stirred at room temperature for 3 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate (15 ml) and ethyl acetate to extract the organic layer, and washed with saturated brine (30 ml), and then solvent was evaporated. The residue was purified by silica gel column chromatography (Yamazen, n-hexane:ethyl acetate=3:1) to obtain the title compound (30 mg).

後処理

  1. extractionto extract the organic layer
  2. washwashed with saturated brine (30 ml)
  3. customsolvent was evaporated
  4. customThe residue was purified by silica gel column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-f45fcde5a4ab4e70b6e228efd2a90392
出典データセット
uspto-grants-2012_12
特許番号
US08334314B2

反応ノート

読み込み中…