Toluene → HCID 22744566、化合物

HRID 47292ノート

反応式

HRID 47292 の反応式
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[N:13])=[CH:9][CH:10]=2)[C:5]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([Cl:24])[CH:17]=2)=[N:4][N:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCCC1>[ClH:1].[Cl:24][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[O:22][CH3:23])[CH2:15][NH:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([C:12]#[N:13])[CH:7]=2)[C:2]([C:30]2[CH:31]=[CH:32][C:27]([O:26][CH3:25])=[CH:28][CH:29]=2)=[N:3][N:4]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 104510651-Chloro-4-((3-chloro-4-methoxybenzyl)amino)-6-phthalazinecarbonitrileHCID 147699944-Methoxyphenyl boric acid

生成物 1

HCID 22744566HCID 22744566、化合物収率 39.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

423 mg of tetrakis(triphenylphosphine)palladium (0) was added to a mixture of 1.0 g 1-chloro-4-(3-chloro-4-methoxybenzyl)amino-6-cyanophthalazine, 423 mg 4-methoxyphenylboric acid, 30 ml toluene, 30 ml tetrahydrofuran, and 30 ml of 2 M aqueous sodium carbonate in a nitrogen atmosphere. The mixture was stirred at 80° C. for 2 hr, and further at 10° C. for 15.5 hr. The reaction solution was returned to room temperature and extracted with aqueous ammonium chloride and ethyl acetate. The organic layer was washed with aqueous ammonia, water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography. The resulting coupled compound was dissolved in ethyl acetate/ethanol, 4 N hydrochloric acid/ethyl acetate solution was added thereto, and the resulting crystals were collected by filtration to give 460 mg of the title compound as a yellow powder.

後処理

  1. waitfurther at 10° C. for 15.5 hr
  2. customwas returned to room temperature
  3. extractionextracted with aqueous ammonium chloride and ethyl acetate
  4. washThe organic layer was washed with aqueous ammonia, water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography
  8. dissolutionwas dissolved in ethyl acetate/ethanol
  9. addition4 N hydrochloric acid/ethyl acetate solution was added
  10. filtrationthe resulting crystals were collected by filtration

出典と根拠

ORDレコード
ord-6257cec960914e50853ae8212f755a5f
出典データセット
uspto-grants-2004_03
特許番号
US06699870B2

反応ノート

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