Dimethylformamide → HCID 68898032, compound

HRID 1437471Notes

Reaction equation

HRID 1437471 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[N:10]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[OH:31])[C:11]3[C:12]([N:23]=2)=[N:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:16]=3)[CH:6]=[CH:7][CH:8]=1.[C:32]([O:35][CH2:36][CH2:37]Br)(=[O:34])[CH3:33].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:32]([O:35][CH2:36][CH2:37][O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:16]=2)[N:23]=[C:9]1[C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 57941023HCID 57941023, compound

Product 1

HCID 68898032HCID 68898032, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution consisting of 2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenol (Compound of Example 157) (41 mg), bromoethyl acetate (18 mg), N,N-dimethyl formamide (1 ml) was added potassium carbonate (19 mg), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure, and the resulting crystals were collected by filtration to obtain [2-[[2-(3-methoxyphenyl)-6-phenyl-1H-imidazo[4,5-b]pyridin-1-yl]methyl]phenoxy]ethyl acetate (37 mg, 74%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure
  5. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c99aeb2ece54499fb56c8419d3356bec
Source dataset
uspto-grants-2009_11
Patent number
US07622479B2

Reaction notes

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