Potassium Carbonate → 1-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-3-(methylamino)furo-[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

HRID 8793Notes

Reaction equation

HRID 8793 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:24]([N:25](C)[C:26](=O)C(F)(F)F)=[C:23]([C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:24]([NH:25][CH3:26])=[C:23]([C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 21984837N-[5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(2,2-dimethylpropanoyl)furo[2,3-b]pyridin-3-yl]-2,2,2-trifluoro-N-methylacetamide

Product 1

HCID 100969791-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-3-(methylamino)furo-[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of the product from Step A (0.0703 mmol) in methanol (2 mL) and water (0.1 mL) was treated with potassium carbonate (0.049 g; 0.351 mmol) at room temperature. The reaction mixture was stirred a room temperature until the reaction was judged complete by TLC analysis. The reaction mixture was then partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient) gave the title compound. HPLC/MS: 487.0 (M+1), 489.0 (M+3); Rt=5.03 min.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and saturated NaHCO3 solution
  2. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Sources & evidence

ORD record
ord-679402d1219b469b81cbcf32fa23699d
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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