Methanol → 4-Methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid

HRID 1692391Notes

Reaction equation

HRID 1692391 reaction equation
C[O:2][C:3](=[O:23])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[N:6][C:5]=1[O:21]C.B(Br)(Br)Br.CO>C(Cl)Cl>[CH3:10][C:9]1[CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:12]=2)[NH:6][C:5](=[O:21])[C:4]=1[C:3]([OH:23])=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 57441128HCID 57441128, compound2×

Product 1

HCID 574411294-Methyl-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydro-pyridine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.325 g (1.0 mmol) of 2-methoxy-4-methyl-6-(3-trifluoromethyl-phenyl)-nicotinic acid methyl ester (intermediate 12C) in 10 ml of CH2Cl2 was cooled down to 0° C., 2.0 ml (2.0 mmol) of a solution of boron tribromide (1 molar in CH2Cl2) was added drop by drop and the reaction mixture was subsequently warmed up to RT. After two hours, 1.0 ml of MeOH was added and 90 min later, the reaction mixture was evaporated. The crude intermediate formed was used without purification in the next step.

Workup

  1. customthe reaction mixture was evaporated

Sources & evidence

ORD record
ord-ba1b43a1631e4f1c86b9f9c2204d7060
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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