Triethylamine → N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

HRID 494157

反応式

HRID 494157 の反応式
I[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:4][CH:3]=1.[CH2:27]([N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40])[CH:28]=[CH2:29].C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[O:40]=[C:31]1[C:32]2[C:33](=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:34](=[O:35])[N:30]1[CH2:27]/[CH:28]=[CH:29]/[C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]2[C:12]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:19][CH:18]=3)=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 224401N-AllylphthalimideHCID 21895284N-(4-iodophenyl)-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide

生成物 1

HCID 21895288N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4'-(trifluoromethyl)-[1,1'-biphenyl]-2-carboxamide収率 50.6%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of intermediate (1) (0.012 mol), N-allyl-phthalimide (0.012 mol), palladium(II) acetate (0.001 mol) and triethylamine (0.024 mol) was stirred at 100° C. for 12 hours in a bomber, then dissolved in DCM and washed with K2CO3 10%. The organic layer was separated, dried, filtered, and the solvent was evaporated. The residue was crystallized from ACN. The precipitate was filtered off and dried, yielding 3.2 g of N-[4-[(1E)-3-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-propenyl]phenyl]-4′-(trifluoromethyl)-[1,1′-biphenyl]-2-carboxamide (intermediate 2; mp. 190° C.).

後処理

  1. washwashed with K2CO3 10%
  2. customThe organic layer was separated
  3. customdried
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was crystallized from ACN
  7. filtrationThe precipitate was filtered off
  8. customdried

出典と根拠

ORDレコード
ord-74177f64702f4b5ea71e9855ace6de15
出典データセット
uspto-grants-2009_05
特許番号
US07538124B2

関連ノート

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