Dimethylformamide → HCID 70926048, compound

HRID 1023884Notes

Reaction equation

HRID 1023884 reaction equation
[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:10]=1[CH:11]=[N:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:26][N:27](C=O)[CH3:28]>>[CH2:1]([O:8][C:9]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:10]=1[C:11]1[N:12]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:28]=[N:27][CH:26]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 67206355HCID 67206355, compound

Product 1

HCID 70926048HCID 70926048, compoundYield 21%

Procedure

To a solution of N-(2-(benzyloxy)-5-chlorobenzylidene)pyridin-3-amine (0.929 mmol) in DMF (3 mL) at room temperature, was added NaH (1.12 mmol) and the solution was stirred for 1 h, followed by the addition of imine (0.929 mmol). After stirring for 4 d, the reaction mixture was diluted with satd. NH4Cl solution and the product was extracted with EtOAc. The combined organic extract was dried (Na2SO4) and concentrated to afford the crude. Chromatographic purification afforded the final product. Yield 21%. 1H NMR: 4.64 (s, 2H), 6.70 (d, 1H), 6.96 (m, 2H), 7.16-7.30 (m, 8H), 7.71 (s, 1H), 8.31 (d, 1H, J=2.4 Hz), 8.53 (dd, 1H, J=1.8 Hz, 3.0 Hz)

Workup

  1. stirringAfter stirring for 4 d
  2. additionthe reaction mixture was diluted with satd
  3. extractionNH4Cl solution and the product was extracted with EtOAc
  4. extractionThe combined organic extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated
  7. customto afford the crude
  8. customChromatographic purification

Sources & evidence

ORD record
ord-ff101d8f408f43a88dc043d2958b3c64
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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