Triethylamine → {3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl Ester

HRID 34110

反応式

HRID 34110 の反応式
[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](I)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].[F:38][C:39]1[CH:46]=[CH:45][C:42]([CH:43]=[CH2:44])=[CH:41][CH:40]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:37])[NH:7][C:8]1[CH:9]=[C:10]2[C:16](/[CH:44]=[CH:43]/[C:42]3[CH:45]=[CH:46][C:39]([F:38])=[CH:40][CH:41]=3)=[N:15][N:14]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:11]2=[CH:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 68926908(3-Iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic Acid Tert-Butyl Ester

生成物 1

HCID 68931002{3-[(E)-2-(4-Fluorophenyl)vinyl]-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl}carbamic Acid Tert-Butyl Ester収率 68.2%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

To a solution of 400 mg of (3-iodo-1-trityl-1H-pyrazolo[3,4-c]pyridin-5-yl)carbamic acid tert-butyl ester and 162 mg of 4-fluorostyrene in 2.0 mL of N,N-dimethylformamide were added 15 mg of palladium acetate, 40 mg of 2-(di-tert-butylphosphino)biphenyl and 0.46 mL of triethylamine at room temperature, and stirred at 80° C. for 6 hours. After diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3). The resultant crystals were washed with diethyl ether, to afford 270 mg of the title compound as colorless crystals.

後処理

  1. washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-dichloromethane:n-hexane=1:1-ethyl acetate:n-hexane=1:3)
  6. washThe resultant crystals were washed with diethyl ether

出典と根拠

ORDレコード
ord-5bc733d0f6204d94be8247f1050b8975
出典データセット
uspto-grants-2008_09
特許番号
US07429609B2

関連ノート

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