2-Bromo-5-(ethylsulfonyl)pyridine → [4-(5-Ethanesulfonyl-pyridin-2-yloxy)-3,6-difluoro-naphthalen-2-yl]-acetic acid methyl ester

HRID 238621

Reaction equation

HRID 238621 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([F:15])=[C:13]([OH:16])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1.Br[C:20]1[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH3:30])(=[O:28])=[O:27])=[CH:22][N:21]=1.COC(=O)C(=CC1C=CC(F)=CC=1)CC(O)=O>>[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]([F:15])=[C:13]([O:16][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH2:29][CH3:30])(=[O:27])=[O:28])=[CH:22][N:21]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:17])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 3

HCID 533931842-Bromo-5-(ethylsulfonyl)pyridineHCID 59326617(3,6-Difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterHCID 673037992-(4-Fluoro-benzylidene)-succinic acid 1-methyl ester

Product 1

HCID 59326477[4-(5-Ethanesulfonyl-pyridin-2-yloxy)-3,6-difluoro-naphthalen-2-yl]-acetic acid methyl esterYield 48%

Procedure

Starting with (3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (25 mg, 0.099 mmol) and 2-bromo-5-ethanesulfonyl-pyridine (28 mg, 0.112 mmol), using a method analogous to the one described for the methyl ester of example 1-1, [4-(5-ethanesulfonyl-pyridin-2-yloxy)-3,6-difluoro-naphthalen-2-yl]-acetic acid methyl ester (20 mg, 48%) was obtained as a white solid, which was used in the next step without further purification.

Sources & evidence

ORD record
ord-1ba199307a4f4c2e99abaff2eacf5524
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Linked notes

Loading…