3-(Trifluoromethyl)benzylamine → 6-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamide

HRID 304

Reaction equation

HRID 304 reaction equation
NC(=O)c1ccc(Cl)nc1.NCc1cccc(C(F)(F)F)c1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.COCCOC.[Na+].[Pd]>NC(=O)c1ccc(NCc2cccc(C(F)(F)F)c2)nc1

Participants

7

Reactant 2

HCID 759623-(Trifluoromethyl)benzylamineHCID 804566-Chloronicotinamide

Product 1

HCID 789156536-[[3-(Trifluoromethyl)phenyl]methylamino]pyridine-3-carboxamideYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 4144353Palladium (II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 6-chloronicotinamide (0.053 g, 0.34 mmol), sodium 2-methylpropan-2-olate (0.065 g, 0.68 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.020 g, 0.03 mmol) and diacetoxypalladium (7.60 mg, 0.03 mmol) in DME (1 mL) was added (3-(trifluoromethyl)phenyl)methanamine (0.049 mL, 0.34 mmol). The reaction was run in microwave at 120 C for 4h. only traces of product observed. Reaction wasted.

Sources & evidence

ORD record
ord-058876800e774f05bf1b52bd00238231
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Linked notes

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