Ethanone,1-(2-fluoro-4-pyridinyl)- synthesis
- Product Name:Ethanone,1-(2-fluoro-4-pyridinyl)-
- CAS Number:111887-72-0
- Molecular formula:C7H6FNO
- Molecular Weight:139.13
Yield:111887-72-0 96%
Reaction Conditions:
Stage #1: 2-fluoro-N-methyl-N-(methyloxy)-4-pyridinecarboxamide;methylmagnesium bromide in tetrahydrofuran;diethyl ether at 0;
Stage #2: with ammonium chloride in tetrahydrofuran;diethyl ether;water;Saturated solution;
Steps:
1-86
[0356] l-(2-Fluoro-4-pyridinyl)ethanone (147). A solution of MeMgBr (3 M in Et2O, 3.8 mL, 11.4 mmol) was added slowly to a stirred solution of amide 146 (1.4 g, 7.6 mmol) in dry THF (40 mL) at 0 0C and the mixture was stirred at 0 0C for 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution (15 mL) and the mixture extracted with EtOAc (3 x 50 mL). The combined organic fraction was washed with water (50 mL) washed with brine (50 mL), dried and the solvent evaporated. The residue was purified by column chromatography, eluting with 30% EtO Ac/pet, ether, to give ketone 147 (1.01 g, 96%) as a colourless liquid that crystallized upon standing: mp (EtOAc/pet. ether) 38-39 0C; 1H NMR (CDCl3) 5 8.41 (d, J= 5. I Hz, 1 H, H-6'), 7.63 (ddd, J= 5.2, 3.2, 1.2 Hz, 1 H, H-5'), 7.37 (br s, 1 H, H-3'), 2.63 (s, 3 H, H-2); MS m/z 140.5 (MH+), 172.5 (MH+ + MeOH, 100%).
References:
WO2009/114552,2009,A1 Location in patent:Page/Page column 156
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