Ethyl Acetate → 5-Bromo-1-(cyclopropylmethyl)-3-methylpyridin-2-one

HRID 575723Notes

Reaction equation

HRID 575723 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH3:15])[C:11]([OH:14])=[N:12][CH:13]=1.Br[CH2:17][CH:18]1[CH2:20][CH2:19]1.CC(=O)OCC>CN(C=O)C>[Br:7][C:8]1[CH:9]=[C:10]([CH3:15])[C:11](=[O:14])[N:12]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[CH:13]=1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 178422464HCID 178422464, compound

Product 1

HCID 814220925-Bromo-1-(cyclopropylmethyl)-3-methylpyridin-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (1.32 g, 9.57 mmol) was added to 5-bromo-3-methyl-2-hydroxypyridine (600 mg, 3.19 mmol) and bromomethylcyclopropane (861 mg, 6.38 mmol) in DMF (6 mL). After heating at 70° C. for 3 h, EA extractive work up and silca gel chromatography (PE:EA=30:110:1), the title compound (510 mg, yield: 66.0%) was obtained as a white solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.39 (d, J=2.0 Hz, 1H), 7.26 (d, J=2.0 Hz, 1H), 3.77 (d, J=6.8 Hz, 2H), 2.15 (s, 3H), 0.65-0.60 (m, 2H), 0.40-0.37 (m, 2H). LCMS: 242.1; 244.1 (M+H)+

Sources & evidence

ORD record
ord-64dab73572c84a3f9958699ab69ef14b
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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