Diethyl bromomethylmalonate → HCID 66977066, compound

HRID 712238Notes

Reaction equation

HRID 712238 reaction equation
[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[F-].[K+].Br[C:13]([CH3:24])([C:19](OCC)=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C=O)C>[Br:9][C:5]1[CH:4]=[N:3][C:2]2[NH:1][C:19](=[O:20])[C:13]([CH3:24])([C:14]([O:16][CH2:17][CH3:18])=[O:15])[O:8][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 94944Diethyl bromomethylmalonateHCID 522689Potassium FluorideHCID 116940412-Amino-5-bromo-3-hydroxypyridine

Product 1

HCID 66977066HCID 66977066, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To an ice-cold solution of 2-amino-5-bromopyridin-3-ol (1 g, 5.29 mmol) in DMF (10 mL) was added KF (0.77 g, 13.23 mmol) followed by addition of diethyl 2-bromo-2-methylmalonate (1 mL, 5.29 mmol) and the mixture heated up to 60° C. for 4 h. After completion (by TLC), the reaction was cooled, quenched with water and extracted with EtOAc (3×100 mL). The combined organics were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the desired product as an off-white solid (1 g, 60%).

Workup

  1. temperatureAfter completion (by TLC), the reaction was cooled
  2. customquenched with water
  3. extractionextracted with EtOAc (3×100 mL)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-690c71bc75034c109ae0a035428b54ff
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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