Tributylphenyltin → 3-Phenyl-1H-5-indazolecarbonitrile

HRID 503118ノート

反応式

HRID 503118 の反応式
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.C([Sn](CCCC)(CCCC)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)CCC>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:25]1([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=3)[NH:4][N:3]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

5

反応物 2

HCID 607632TributylphenyltinHCID 22260825tert-Butyl 3-bromo-5-cyano-1H-indazole-1-carboxylate

生成物 1

HCID 130669563-Phenyl-1H-5-indazolecarbonitrile収率 57.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

To a solution of 300 mg of tert-butyl 3-bromo-5-cyano-1H-1-indazolecarboxylate produced in Production Example I-14-b in 10 ml dimethylformamide were added 376 mg of tri-n-butyl(phenyl)tin and 54 mg of tetrakis(triphenylphosphine)palladium(0), and the mixture was stirred at 150° C. for 45 minutes. After removing the solvent by distillation, the residue was dissolved in 1.5 ml of ethyl acetate and the mixture was adsorbed by 1.5 g of silica gel. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:toluene=3:97 to 1:19) and the resulting amorphous powder was crystallized from diisopropyl ether, to give 117 mg of the title compound as pale yellow crystals.

後処理

  1. customAfter removing the solvent
  2. distillationby distillation
  3. dissolutionthe residue was dissolved in 1.5 ml of ethyl acetate
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (ethyl acetate:toluene=3:97 to 1:19)
  6. customthe resulting amorphous powder was crystallized from diisopropyl ether

出典と根拠

ORDレコード
ord-ebec3da8230a4b85932f23ec421b8491
出典データセット
uspto-grants-2010_08
特許番号
US07776890B2

反応ノート

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