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

HRID 8795
Notes
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Reaction equation

HRID 8795 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]([C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1)=[O:27].[H-].[Na+].IC.[CH3:38][N:39]([CH:41]=O)[CH3:40]>>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:8]2[CH:9]=[C:10]3[C:41]([N:39]([CH3:38])[CH3:40])=[C:3]([C:26]([C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:27])[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:16][CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9983227[3-Amino-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Product 1

HCID 10256229[5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-3-(dimethylamino)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Conditions

Temperature
0 °C

Procedure

A solution of 0.050 g (0.101 mmol) of the product from Example 26 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.008 g; 60% dispersion; 0.213 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (19 μL; 0.303 mmol). The reaction was warmed to room temperature and stirred for 1 h. 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 50% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 521.9 (M+1), 523.9 (M+3); Rt=3.96 min.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction was warmed to room temperature
  3. stirringstirred for 1 h
  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 50% ethyl acetate-hexane gradient)

Sources & evidence

ORD record
ord-9ab14d756ba14936bc6b2f503da78bc2
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07091216B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes