Dimethylformamide → HCID 90020217, compound

HRID 2200105Notes

Reaction equation

HRID 2200105 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=1[F:19].C([O-])([O-])=O.[Cs+].[Cs+].CN(C=O)C>O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]=2[F:19])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 844322-Chloropyridin-4-amineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 90020217HCID 90020217, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 2-chloropyridin-4-amine (500 mg, 3.9 mmol), 1,2-difluoro-4-nitrobenzene (620 mg, 3.9 mmol), Cs2CO3 (3.2 g, 9.8 mmol) to DMF (15 mL). Stir the reaction at 110° C. for 16 hrs. Cool to room temperature, add water (100 mL), extract with EtOAc (15 mL×3). Combine the organic layers and wash with brine, dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:4) affords the title compound (280 mg, 27%). MS: (M+1): 268.1.

Workup

  1. customthe reaction at 110° C. for 16 hrs
  2. extractionextract with EtOAc (15 mL×3)
  3. washCombine the organic layers and wash with brine
  4. dry with materialdry over anhydrous Na2SO4
  5. concentrationConcentrate under reduced pressure
  6. customto give the crude product
  7. customPurification by chromatography (silica gel, EtOAc:PE=1:4)

Sources & evidence

ORD record
ord-735140d47b114c9eaeec61895ae4fd17
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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