Triethylamine → 5-(2,4-difluoro-phenylethynyl)-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine

HRID 730000Notes

Reaction equation

HRID 730000 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([NH2:11])=[N:10][C:5]2=[CH:4][CH:3]=1.CCN(CC)CC.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33])#[CH:25]>C1(C)C=CC=CC=1>[F:33][C:27]1[CH:28]=[C:29]([F:32])[CH:30]=[CH:31][C:26]=1[C:24]#[C:25][C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:9]([NH2:11])=[N:10][C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 50638201-Ethynyl-2,4-difluorobenzeneHCID 860636325-bromo-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine

Product 1

HCID 688695425-(2,4-difluoro-phenylethynyl)-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamineYield 40.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Combine 5-bromo-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-ylamine (30.00 g, 105.94 mmol), Et3N (60 mL), and Pd(OAc)2[P(Ph)3]2 (3.97 g, 5.30 mmol) in toluene (150 mL) and heat the resulting mixture to ˜65° C. under nitrogen. Add 1-ethynyl-2,4-difluoro-benzene (21.95 g, 158.92 mmol) in toluene (30 mL) dropwise to the above mixture, and then heat the resulting reaction mixture at 80° C. for 3 h. Cool the reaction to 25° C. and quench with saturated aqueous NH4Cl (300 mL). Stir the resulting reaction mixture at room temperature for 20 minutes, then filter, washing the solid with H2O and drying under vacuum filtration for 30 minutes. Slurry the solid in MTBE (200 mL), then filter and rinse with MTBE (50 mL). Dry the recovered solid under vacuum filtration to provide 14.47 g of the title compound as a light-yellow solid.

Workup

  1. customthe resulting reaction mixture at 80° C. for 3 h
  2. temperatureCool
  3. customthe reaction to 25° C.
  4. customquench with saturated aqueous NH4Cl (300 mL)
  5. customthe resulting reaction mixture at room temperature for 20 minutes
  6. filtrationfilter
  7. washwashing the solid with H2O
  8. customdrying under vacuum filtration for 30 minutes
  9. filtrationfilter
  10. washrinse with MTBE (50 mL)
  11. customDry the recovered solid
  12. filtrationunder vacuum filtration

Sources & evidence

ORD record
ord-100cf9751bfc4516b95c072c8b787dce
Source dataset
uspto-grants-2009_09
Patent number
US07582652B2

Reaction notes

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