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 923204노트

반응식

HRID 923204 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-68e73da8e7cb4d75bc228a9c5938d38f
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278971B2

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