Water → HCID 59443772, compound

HRID 2078395Notes

Reaction equation

HRID 2078395 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[C:5]([OH:8])=[N:6][CH:7]=1.[CH3:11][O:12][C:13](=[O:18])[C:14](Br)([CH3:16])[CH3:15].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[CH3:11][O:12][C:13](=[O:18])[C:14]([O:8][C:5]1[C:4]([CH:9]=[O:10])=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 178519658HCID 178519658, compound

Product 1

HCID 59443772HCID 59443772, compoundYield 47.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
126 °C

Procedure

A mixture of 5-chloro-2-hydroxy-pyridine-3-carbaldehyde (8 g, 51 mmol), 2-bromo-2-methyl-propionic acid methyl ester (27.6 g, 153 mol), Cs2CO3 (28 g, 86.7 mol) in DMF (80 mL) was heated at 126° C. for 3 h. After cooled to room temperature, the mixture was poured into water and extracted with EtOAc. The organic layer was washed with water and brine, dried and concentrated. The residue was purified by flash column to give the title compound (6.2 g).

Workup

  1. temperatureAfter cooled to room temperature
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-d471b457f6494b42adc6f5cd3bce93e7
Source dataset
uspto-grants-2011_04
Patent number
US07928233B2

Reaction notes

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