Triethylamine → 6-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-nitro-1-trityl-1H-indazole

HRID 34038

反応式

HRID 34038 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:14])=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[F:34][C:35]1[CH:42]=[CH:41][C:38]([CH:39]=[CH2:40])=[CH:37][CH:36]=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([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:7]1[CH:6]=[C:5]2[C:10]([C:2](/[CH:40]=[CH:39]/[C:38]3[CH:41]=[CH:42][C:35]([F:34])=[CH:36][CH:37]=3)=[N:3][N:4]2[C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:9][C:8]=1[N+:11]([O-:13])=[O:12]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 678834-FluorostyreneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 689283003-bromo-6-fluoro-5-nitro-1-trityl-1H-indazole

生成物 1

HCID 689284926-Fluoro-3-[(E)-2-(4-fluorophenyl)-vinyl]-5-nitro-1-trityl-1H-indazole収率 46.8%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

To a solution of 600 mg of 3-bromo-6-fluoro-5-nitro-1-trityl-1H-indazole in 6 mL of N,N-dimethylformamide were successively added 292 mg of 4-fluorostyrene, 71 mg of 2-(di-tert-butylphosphino)biphenyl, 27 mg of palladium acetate (II) and 0.85 mL of triethylamine, and stirred at 80° C. for 6.5 hours. The solvent was evaporated, and the resulting residue was dissolved in 25 mL of ethyl acetate. The organic layer was successively washed with water (twice) and saturated brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated. The obtained crude crystal was recrystallized from ethyl acetate-diisopropylether, to afford 304 mg of the title compound as bright yellow crystals.

後処理

  1. customThe solvent was evaporated
  2. dissolutionthe resulting residue was dissolved in 25 mL of ethyl acetate
  3. washThe organic layer was successively washed with water (twice) and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained crude crystal
  7. customwas recrystallized from ethyl acetate-diisopropylether

出典と根拠

ORDレコード
ord-3c4fee8c4bba47369bf067c0e1d01924
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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