2,5-Dichloro-4-iodopyridine → 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide
Reaction equation
CNC(=O)c1ccc(F)cc1N.Clc1cc(I)c(Cl)cn1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>CNC(=O)c1ccc(F)cc1Nc1cc(Cl)ncc1ClParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
diacetoxypalladium (6.15 mg, 0.03 mmol) was added to a stirred suspension of 2,5-dichloro-4-iodopyridine (150 mg, 0.55 mmol), 2-amino-4-fluoro-N- methylbenzamide (92 mg, 0.55 mmol) (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (31.7 mg, 0.05 mmol) and cesium carbonate (268 mg, 0.82 mmol) in 1,4-dioxane (2.5 mL) under nitrogen. The resulting suspension was stirred at 100 °C for 16 hours. The mixture was cooled to RT; filtered the solvent was evaporated. The crude product was absorbed on silica gel and purified by flash chromatography on silica gel eluting with 20 to 80% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2,5-dichloropyridin-4-ylamino)-4-fluoro-N-methylbenzamide (60.0 mg, 34.9 %) as a beige solid.
Sources & evidence
- ORD record
- ord-6e62fa456f9543438c4d7ca789bf180e
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Reaction notes
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