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

HRID 8794

Reaction equation

HRID 8794 reaction equation
NC1[C:10]2[C:5](=[N:6][C:7]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)[CH:9]=2)[O:4][C:3]=1[C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].[H-].[Na+].IC.[CH3:36][N:37]([CH:39]=O)[CH3:38]>>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[CH:9]=[C:10]3[C:39]([N:37]([CH3:36])[CH3:38])=[C:3]([C:26](=[O:31])[C:27]([CH3:29])([CH3:28])[CH3:30])[O:4][C:5]3=[N:6][C:7]=2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=2[Cl:25])=[CH:12][CH:13]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 102542841-(3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl)-2,2-dimethylpropan-1-one

Product 1

HCID 103459281-[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-3-(dimethylamino)furo[2,3-b]pyridin-2-yl]-2,2-dimethylpropan-1-one

Conditions

Temperature
0 °C

Procedure

A solution of 0.050 g (0.106 mmol) of the product from Example 17 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.010 g; 60% dispersion; 0.232 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (26 μL; 0.424 mmol). The reaction was warmed to room temperature and stirred for 2 hours. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was 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: 501.0 (M+1), 503.0 (N+3); Rt=5.08 min.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred for 2 hours
  4. customThe reaction was quenched with saturated NaHCO3 solution
  5. customThe reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution
  6. washThe organic layer was washed twice with saturated NaHCO3 solution, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurification by MPLC (silica gel; 0% to 20% ethyl acetate:hexane gradient)

Sources & evidence

ORD record
ord-f3e770690d984187be9a3bc66ad344d0
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Linked notes

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