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

HRID 1531280Notes

Reaction equation

HRID 1531280 reaction equation
C(NC1CC2C(=CC=C(NC(C3C(C4C=CC(F)=CC=4)=CC=CC=3)=O)C=2)C1)(=O)C.[CH3:30][O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1Cl.[F:41][C:42]([F:53])([F:52])[C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1>>[CH3:30][O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][C:34]=1[C:46]1[CH:47]=[CH:48][C:43]([C:42]([F:53])([F:52])[F:41])=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 819931Methyl 2-chloronicotinateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 543765954'-Fluorobiphenyl-2-carboxylic acid (2-acetylamino-indan-5-yl)-amide

Product 1

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

Procedure

2-(4-Trifluoromethyl-phenyl)-nicotinic acid methyl ester is prepared similarly to the title compound of Example 3 using 2-chloronicotinic acid methyl ester (1.45 g, 8.45 mmol) and 4-trifluoromethylbenzeneboronic acid (2.41 g, 12.68 mmol) to give the product as 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). MS (ES+) m/z 282 (M+1).

Sources & evidence

ORD record
ord-1a0979e85a744932ae514aebb0876d20
Source dataset
uspto-grants-2001_03
Patent number
US06197798B1

Reaction notes

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