Methyl 2-chloronicotinate → 2-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester

HRID 1814786Notes

Reaction equation

HRID 1814786 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1Cl.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1>[Pd]>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[N:6][C:5]=1[C:17]1[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 819931Methyl 2-chloronicotinateHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 539509912-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester is prepared by palladium [PdCl2 (dppf)] catalyzed coupling of 2-chloronicotinic acid methyl ester (1.45 g, 8.45 mmol) and 4-trifluoromethylbenzeneboronic acid (2.41 g, 12.68 mmol) to give an oil: 1H NMR (CDCl3, 300 MHz): δ 8.80 (1H dd), 8.19 (1H, dd), 7.67 (4H, q), 7.40 (1H, dd), 3.70 (3H, s).

Workup

  1. customto give an oil

Sources & evidence

ORD record
ord-ac6f497a3e8d48899ee1e822bf022c00
Source dataset
uspto-grants-2005_04
Patent number
US06878707B2

Reaction notes

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