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 923204Notes

Reaction equation

HRID 923204 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-68e73da8e7cb4d75bc228a9c5938d38f
Source dataset
uspto-grants-2016_03
Patent number
US09278971B2

Reaction notes

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