2-Chloronicotinoyl chloride → HCID 10845620, compound

HRID 2294133Notes

Reaction equation

[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[Cl:6][C:7]1[N:15]=[CH:14][CH:13]=[CH:12][C:8]=1[C:9](Cl)=[O:10]>C1COCC1.[Cu]I>[Cl:6][C:7]1[C:8]([C:9](=[O:10])[C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:12][CH:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of copper(I) iodide (1.18 g, 6.2 mmol) in 5 mL of THF was cooled to -40° C. and then tert-butyllithium (8.85 mL, 1.4M, 12.4 mmol) was added. The mixture was stirred for 1 hour and 2-chloronicotinic acid chloride (2 g, 11.3 mmol) was added dropwise. The mixture was stirred at -40° C. for 1.5 hours and then allowed to warm to room temperature. The mixture was quenched with water and then diluted with ethyl acetate. The mixture was filtered, washed with water (2×10 mL) and brine, dried (Na2SO4) and concentrated. The residue was purified on silica gel by flash chromatography eluting with hexanes/ethyl acetate (85:15) to give 1-(2-chloro-3-pyridyl)-2,2-dimethylpropan-1-one (1.735 g, 8.8 mmol) as an oil.

Workup

stirringThe mixture was stirred at -40° C. for 1.5 hours
temperatureto warm to room temperature
customThe mixture was quenched with water
additiondiluted with ethyl acetate
filtrationThe mixture was filtered
washwashed with water (2×10 mL) and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customThe residue was purified on silica gel by flash chromatography
washeluting with hexanes/ethyl acetate (85:15)

Sources & evidence

ORD record: ord-ef7e4ec74ddb4d92bc339e69e96bf5b4
Source dataset: uspto-grants-1997_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05688795

Reaction notes

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