2-Chloro-5-fluoro-6-methylnicotinonitrile synthesis
- Product Name:2-Chloro-5-fluoro-6-methylnicotinonitrile
- CAS Number:474826-15-8
- Molecular formula:C7H4ClFN2
- Molecular Weight:170.57
13061-96-6
297 suppliers
$6.00/1g
82671-02-1
228 suppliers
$10.00/5g
474826-15-8
15 suppliers
inquiry
Yield: 11%
Reaction Conditions:
with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;sodium carbonate in water;N,N-dimethyl-formamide at 80; for 4 h;
Steps:
jlntermediate 23J - 2-Chloro-5-fluoro-6-methylpyridine-3-carbonitrile
2, 6-Dichloro-5 -fluoropyridine-3 -carbonitrile (250 mg, 1.31 mmol), methylboronic acid (78 mg, 1.31 mmol), PdC12(dppf) (48 mg, 0.07 mmol) and sodium carbonate (416 mg, 3.93 mmol) were suspended in 2:1 DMF / H20 (6 ml) and the mixture was stirred at 80 °C for 4 hours. The reaction was filtered through Celite and washed with EtOAc (20 ml). To the filtrate was added water (30 ml). The organics were separated and the aqueous phase extracted with EtOAc (3 x 30 ml). The combined organics were washed with brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified via flash column chromatography (gradient of 0 - 100% EtOAc in heptane followed by 0-100% MeOH in EtOAc). The product-containing fractions were combined and concentrated in vacuo to give the title compound as a white solid (24 mg, 11%).1H NIVIR (250 MHz, Chloroform-d) 7.65 (s, 1H), 2.60 (s, 3H). LCMS Method 2 - Tr = 0.99 mm (ES+) (M+H)+ 143.5
References:
NAVITOR PHARMACEUTICALS, INC.;O'NEILL, David John;SAIAH, Eddine;KANG, Seong Woo Anthony;BREARLEY, Andrew;BENTLEY, Jonathan WO2018/89433, 2018, A1 Location in patent:Paragraph 00304