Dimethylformamide → 5-Fluoro-1-methyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde

HRID 509937Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4](I)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C([Mg]Cl)(C)C.CN(C)[CH:18]=[O:19]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[O:19])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

5-Fluoro-3-iodo-1-methyl-1H-pyridin-2-one (32, 120.5 g, 476 mmol) was dissolved in 2381 mL of tetrahydrofuran and cooled to −40° C. in a dry ice acetone bath. Isopropylmagnesium chloride (310 mL, 619 mmol) was added dropwise and the mixture was stirred for 30 minutes. Then 92 mL of N,N-dimethylformamide was added and the mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched by adding 200 mL of 10% aqueous hydrochloric acid, then concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 100% ethyl acetate. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a yellow solid (33, 35 g, 226 mmol, 47.4%).

Workup

temperatureto warm to room temperature
stirringstirred overnight
customThe reaction was quenched
additionby adding 200 mL of 10% aqueous hydrochloric acid
concentrationconcentrated under vacuum
customThe resulting material was purified by silica gel column chromatography
washeluting with 100% ethyl acetate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e3b445fa1688403992148495886b2651
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096593B2

Reaction notes

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