N,N-Diethyl-2-propanamine → 3-(Imidazo[1,2-a]pyridin-3-ylethynyl)-4-methyl-n-(3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

HRID 923204ノート

反応式

HRID 923204 の反応式
I[C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[CH3:27])[C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:10]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)[CH:9]=1)=[O:6].C(N(CC)C(C)C)C.[C:36]([C:38]1[N:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]2=[N:40][CH:39]=1)#[CH:37]>CN(C=O)C.[Cu]I>[N:40]1[CH:39]=[C:38]([C:36]#[C:37][C:2]2[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=2[CH3:27])[C:5]([NH:7][C:8]2[CH:13]=[C:12]([C:14]([F:16])([F:17])[F:15])[CH:11]=[C:10]([N:18]3[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]3)[CH:9]=2)=[O:6])[N:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=12

参加物

6

反応物 3

HCID 521913N,N-Diethyl-2-propanamineHCID 177521583-Iodo-4-methyl-N-[3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl]benzamideHCID 468387593-Ethynylimidazo[1,2-a]pyridine

生成物 1

HCID 248266313-(Imidazo[1,2-a]pyridin-3-ylethynyl)-4-methyl-n-(3-(4-methyl-1h-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-iodo-4-methyl-N-(3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)benzamide (0.11 g, 0.22 mmol.) in DMF (1 mL) in a sealed tube was added Pd[(PPh3)4](0.013 g, 0.011 mmol), CuI (3 mg, 0.016 mmol), diethylisopropylamine (0.057 mL, 0.33 mmol.), followed by 3-ethynylimidazo[1,2-a]pyridine (0.040 g, 0.28 mmol.). The mixture was purged with argon for 15 minutes, sealed and stirred at rt for 28 h. The solvent was concentrated and the residue was taken up in methylene chloride (50 mL). The organic layer was washed with water, dried (Na2SO4) and evaporated to leave a brown residue which was purified by combiflash (hexane/ethyl acetate/methanol) to yield the desired material: MS (M+H)+ 500.

後処理

  1. customThe mixture was purged with argon for 15 minutes
  2. customsealed
  3. concentrationThe solvent was concentrated
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto leave a brown residue which
  8. customwas purified by combiflash (hexane/ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-68e73da8e7cb4d75bc228a9c5938d38f
出典データセット
uspto-grants-2016_03
特許番号
US09278971B2

反応ノート

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