N-methyl-2-pyrrolidone → HCID 69155969、化合物

HRID 750150ノート

反応式

HRID 750150 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11](Br)=[CH:10][CH:9]=2)=[O:4].[CH3:33][N:34]1CCCC1=O>[C-]#N.[Zn+2].[C-]#N.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.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:23][C:24]2[CH:32]=[CH:31][C:27]3[O:28][CH2:29][O:30][C:26]=3[CH:25]=2)[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([C:33]#[N:34])=[CH:10][CH:9]=2)=[O:4]

参加物

6

反応物 2

HCID 13387N-methyl-2-pyrrolidoneHCID 10239063HCID 10239063、化合物

生成物 1

HCID 69155969HCID 69155969、化合物

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-(benzo[1,3]dioxol-5-ylmethyl)-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (300 mg), zinc cyanide (50 mg), tetrakis(triphenylphosphine)palladium(0) (35 mg) and 1-methyl-2-pyrrolidone (3 ml) was stirred at 100° C. for 2 hrs. under an argon atmosphere. Water was added to the reaction mixture, and the mixture was extracted with a mixture of ethyl acetate and THF. The organic layer was washed with aqueous ammonia, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate). The solvent was evaporated under reduced pressure, and the obtained crystals were washed with a mixture of ethyl acetate and diethyl ether to give the title compound (210 mg).

後処理

  1. extractionthe mixture was extracted with a mixture of ethyl acetate and THF
  2. washThe organic layer was washed with aqueous ammonia, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)
  6. customThe solvent was evaporated under reduced pressure
  7. washthe obtained crystals were washed with a mixture of ethyl acetate and diethyl ether

出典と根拠

ORDレコード
ord-9a1839bc5c5a40d288339afda773b024
出典データセット
uspto-grants-2008_07
特許番号
US07402595B2

反応ノート

読み込み中…