Acetic Acid → [3-Cyclopropyl-4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester

HRID 238646Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH2:27][CH3:28])(=[O:26])=[O:25])=[CH:20][N:19]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1.[N+](=[CH2:33])=[N-].C(O)(=O)C>O1CCCC1.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:30])[CH2:4][C:5]1[C:14]([CH:15]2[CH2:33][CH2:16]2)=[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([S:24]([CH2:27][CH3:28])(=[O:25])=[O:26])=[CH:20][N:19]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:29])[CH:11]=2)[CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution of [4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester (6.0 mg, 0.014 mmol, methyl ester of example 17-1) in tetrahydrofuran, was added a solution of diazomethane (0.1 M, 5 mL) in diethyl ether at 0° C. under an argon atmosphere, followed by palladium acetate (1 mg) in two portions. After being stirred at 0° C. for 2 hours, the reaction mixture was treated with acetic acid (0.2 mL) to quench the reaction, and then filtered. The filtrate was concentrated in vacuo to afford the crude product of [3-cyclopropyl-4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-naphthalen-2-yl]-acetic acid methyl ester as a yellow oil.

Workup

customto quench
customthe reaction
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-1213790bed974984a52c27cd3c734d51
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642629B2

Reaction notes

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