Methyl Acetate → [4-(3-Bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238649

Reaction equation

HRID 238649 reaction equation
[CH3:1][O:2][C:3](=[O:5])[CH3:4].[Br:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[C:11]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])[CH:12]=1.COC(=O)[C:22](=[CH:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[CH:23]([CH3:27])[C:24]([OH:26])=O>>[CH3:1][O:2][C:3](=[O:5])[CH2:4][C:22]1[C:23]([CH3:27])=[C:24]([O:26][C:8]2[C:7]([Br:6])=[CH:12][C:11]([S:13]([CH2:16][CH3:17])(=[O:15])=[O:14])=[CH:10][N:9]=2)[C:30]2[C:29](=[CH:34][CH:33]=[C:32]([F:35])[CH:31]=2)[CH:28]=1

Participants

4

Reactant 3

HCID 6584Methyl AcetateHCID 593265653-Bromo-2-chloro-5-(ethylsulfonyl)pyridineHCID 667755872-(4-Fluoro-benzylidene)-3-methyl-succinic acid 1-methyl ester

Product 1

HCID 59326492[4-(3-Bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl esterYield 73.9%

Procedure

Starting with 6-fluoro-4-hydroxy-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (124 mg, 0.50 mmol) and 3-bromo-2-chloro-5-ethanesulfonyl-pyridine (157 mg, 0.55 mmol), using a method analogous to the one described for the methyl ester of example 2-1, [4-(3-bromo-5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-methyl-naphthalen-2-yl]-acetic acid methyl ester (183 mg, 73.9%) was obtained as a white solid.

Sources & evidence

ORD record
ord-1794439bd43c4443a22a56ee45e8677f
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Linked notes

Loading…