Reaction equation
CNC(=O)c1ccccc1N.FC(F)(F)c1cnc(Cl)cc1I>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)c1ccccc1Nc1cc(Cl)ncc1C(F)(F)FParticipants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 90 °C
Procedure
2-chloro-4-iodo-5-(trifluoromethyl)pyridine (500 mg, 1.63 mmol), 2-amino-N- methylbenzamide (244 mg, 1.63 mmol), diacetoxypalladium (29.2 mg, 0.13 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (151 mg, 0.26 mmol) and cesium carbonate (636 mg, 1.95 mmol) were mixed together in dioxane (10 mL). Reaction was degassed with nitrogen and was stirred at 90 °C overnight under nitrogen. Reaction was filtered, washed with CH2Cl2 and filtrate was concentrated to dryness. The crude product was purified by flash chromatography on silica gel eluting with 10 to 50% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 2-(2-chloro-5-(trifluoromethyl)pyridin-4-ylamino)-N-methylbenzamide (340 mg, 63.4 %) as a pale yellow solid.
Sources & evidence
- ORD record
- ord-59518020213f4a99980578b9463ad852
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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