1-Bromo-2-methylpropane → HCID 59214340, compound

HRID 2192483Notes

Reaction equation

HRID 2192483 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:15][CH:16]([CH3:18])[CH3:17]>CN(C)C=O>[CH3:15][CH:16]([CH3:18])[CH2:17][N:3]1[CH:4]=[CH:5][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:7][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 178498433HCID 178498433, compound

Product 1

HCID 59214340HCID 59214340, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-hydroxy-4-pyridinecarboxylate (D26; 1.02 g, 6.66 mmol) in N,N-dimethylformamide (20 ml) was added sodium hydride (60%; 0.293 g, 7.33 mmol). The resulting solution was stirred at room temperature for 15 mins. 1-Bromo-2-methylpropane (0.87 ml, 7.99 mmol) was then added and the mixture was stirred at 80° C. for 2 hrs. The reaction was quenched with methanol and the solvent was removed under vacuum. The residue was partitioned between ethyl acetate and water, the organic layer dried over magnesium sulphate and concentrated under vacuum. The crude material was purified by chromatography on silica, eluting with 50-80% ethyl acetate in cyclohexane gave the title compound as a light blue solid (450 mg). MS: m/z 210 [MH+]. O-alkylated material was also isolated.

Workup

  1. stirringthe mixture was stirred at 80° C. for 2 hrs
  2. customThe reaction was quenched with methanol
  3. customthe solvent was removed under vacuum
  4. customThe residue was partitioned between ethyl acetate and water
  5. dry with materialthe organic layer dried over magnesium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe crude material was purified by chromatography on silica
  8. washeluting with 50-80% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-c9653ae70ade4397b6d719e971955dff
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

Loading…