Cesium carbonate → HCID 86695784, compound

HRID 922304Notes

Reaction equation

HRID 922304 reaction equation
C[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[C:4]([OH:10])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:18][C:19]1[CH:34]=[CH:33][C:22]([O:23][CH2:24][C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])=[CH:21][CH:20]=1>CN(C=O)C>[O:26]=[C:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:24][O:23][C:22]1[CH:33]=[CH:34][C:19]([CH2:18][O:10][C:4]2[N:3]=[CH:2][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66685859HCID 66685859, compoundHCID 1784334412-Methyl-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Product 1

HCID 86695784HCID 86695784, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-hydroxypyridine-3-carbaldehyde. (0.25 g, 2 mmol) in DMF (10 mL) was added cesium carbonate (0.97 g, 3 mmol) and stirred at RT for 30 min then added 2-[4-(bromomethyl)phenoxy]-1-phenylethanone (0.61 g, 2 mmol) this resulting mass was stirred at 80° C. for 12 h, reaction quenched with water and extracted with ethyl acetate, Organic layer was washed with water and brine solution dried over anhydrous Na2SO4 and concentrated to afford crude product which was purified by column chromatography to get pale brown solid as product (0.4 g, Yield: 60%); 1H NMR (300 MHz, CDCl3): δ 9.59 (s, 1H) 7.95-8.02 (m, 2H), 7.67-7.78 (m, 3H), 7.54-7.59 (m, 2H), 7.30-7.33 (d, 2H), 6.93-6.96 (d, 2H), 6.49-6.53 (d, 1H), 5.57 (s, 2H), 5.11 (s, 2H).

Workup

  1. customreaction
  2. customquenched with water
  3. extractionextracted with ethyl acetate, Organic layer
  4. washwas washed with water and brine solution
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customto afford crude product which
  8. customwas purified by column chromatography
  9. customto get pale brown solid as product (0.4 g, Yield: 60%)

Sources & evidence

ORD record
ord-41d26bb7a7804d00bc75f147464c6675
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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