Triethylamine → 2-(3,4-Dimethoxybenzenesulphonyl)-4-(2-pyrid-2-ylethynyl)isoindoline

HRID 2146

反応式

HRID 2146 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3Br)[CH2:15]2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)#[CH:32]>CN(C)C=O.[Pd].C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][C:20]=3[C:32]#[C:31][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[CH2:15]2)(=[O:13])=[O:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 137268Ethynylpyridine2 回HCID 196896612-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline

生成物 1

HCID 196896402-(3,4-Dimethoxybenzenesulphonyl)-4-(2-pyrid-2-ylethynyl)isoindoline収率 12.5%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

2-(3,4-Dimethoxybenzenesulphonyl)-4-bromoisoindoline (0.19 g), triethylamine (0.10 ml), 2-ethynylpyridine(0.06 g) and bis (triphenylphosphine)palladium(II)chloride (10%) in anhydrous N,N-dimethylformamide(2 ml) were stirred together under an inert atmosphere and heated to 90° C. After 20 hours further 2-ethynylpyridine(0.12 g) and palladium catalyst (20%) were added and heating continued for 3 days. The reaction mixture at room temperature was diluted with ethyl acetate, filtered through a pad of silica and the filtrate evaporated in vacuo to yield a yellow residue. Purification by column chromatography, eluting with a 20-100% ethyl acetate in hexane gradient afforded the title compound (25 mg).

後処理

  1. temperatureheating
  2. filtrationfiltered through a pad of silica
  3. customthe filtrate evaporated in vacuo
  4. customto yield a yellow residue
  5. customPurification by column chromatography
  6. washeluting with a 20-100% ethyl acetate in hexane gradient

出典と根拠

ORDレコード
ord-1fbe8bec2d7a4b37b8e811f839c2b36c
出典データセット
uspto-grants-1998_03
特許番号
US05728712

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