Reaction equation
NC(=O)c1ccc(Cl)nc1.NCc1ccc(C(F)(F)F)cc1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].COCCOC.[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>NC(=O)c1ccc(NCc2ccc(C(F)(F)F)cc2)nc1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.021 g, 0.03 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (4-(trifluoromethyl)phenyl)methanamine (0.097 mL, 0.68 mmol). The reaction was run in microwave at 100 °C for 4h. The compound was purified by preparative HPLC on a Kromasil C8 column (10 µm 250x20 ID mm) using a gradient of 51-55% acetonitrile in H2O/ACN/FA 95/5/0.2 buffer, over 25 minutes with a flow of 19 mL/min. The compounds were detected by UV at 270nm. 6-(4-(trifluoromethyl)benzylamino)nicotinamide (7.40 mg, 7.40 %) was obtained.
Sources & evidence
- ORD record
- ord-92bacb0740454b4398d7f3969518ce26
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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