Potassium Iodide → [4-(5-Ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester

HRID 238645Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([OH:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:18])[CH:11]=2)[CH:6]=1.C(S([C:25]1[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:33])=[O:32])=[CH:27][N:26]=1)(=O)=O)C.[I-].[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:14]([CH:15]=[CH2:16])=[C:13]([O:17][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH3:35])(=[O:32])=[O:33])=[CH:27][N:26]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:18])[CH:11]=2)[CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (6-fluoro-4-hydroxy-3-vinyl-naphthalen-2-yl)-acetic acid methyl ester (22 mg, 0.084 mmol), 2,5-bis-ethanesulfonyl-pyridine (33 mg, 0.126 mmol), potassium iodide (5 mg), and cesium carbonate (68 mg, 0.21 mmol), N,N-dimethylformamide (0.5 mL) and acetone (1.5 mL) was heated at 100° C. for 30 minutes with microwave irradiation. The mixture was then concentrated in vacuo. The residue was purified by flash column (gradient elution with 0-50% ethyl acetate in petroleum ether) to afford [4-(5-ethanesulfonyl-pyridin-2-yloxy)-6-fluoro-3-vinyl-naphthalen-2-yl]-acetic acid methyl ester (13 mg, 36.1%) as a yellow solid.

Workup

concentrationThe mixture was then concentrated in vacuo
customThe residue was purified by flash column (gradient elution with 0-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-958e24f4586e40a0986164d174043df5
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642629B2

Reaction notes

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