Cesium carbonate → HCID 90389417, compound

HRID 1526595Notes

Reaction equation

HRID 1526595 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][C:21]#[N:22].C(=O)(O)[O-].[Na+]>CN(C=O)C>[C:21]([CH2:20][O:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1)#[N:22]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 516892Sodium BicarbonateHCID 90389409HCID 90389409, compound2×

Product 1

HCID 90389417HCID 90389417, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of methyl 5-hydroxy-3-methylpicolinate (0.8063 g, 4.82 mmol, step 3 intermediate 38) and cesium carbonate (0.772 ml, 9.65 mmol, Alfa Aesar) in DMF (48.2 ml) was added bromoacetonitrile (0.336 ml, 4.82 mmol, Sigma-Aldrich Chemical Company, Inc.). The reaction mixture was stirred for 4 h at rt. The reaction mixture was diluted with aqueous, saturated sodium bicarbonate solution and extracted with EtOAc. The organic extract was washed with aqueous, saturated sodium bicarbonate solution, brine and dried over MgSO4. The filtrate was concentrated in vacuo. MS m/z=207.1 [M+H]+. Calculated for C10H10N2O3: 206.069. 1H NMR (400 MHz, CHLOROFORM-d) ppm 2.67 (s, 3H) 3.98 (s, 3H) 4.88 (s, 2H) 7.20 (d, J=2.35 Hz, 1H) 8.32 (br. s., 1H)

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with aqueous, saturated sodium bicarbonate solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6056093aba67434e8a4b8d05df977b76
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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