HCID 18461172, compound → HCID 18461160, compound

HRID 2303378Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([O:28]C)=[C:24]([F:30])[CH:23]=2)=[O:21])=[CH:5][CH:4]=1>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([F:30])[CH:23]=2)=[O:21])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

500 mg (1.2 mmol) of [2-(4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][3-fluoro-4-methoxyphenyl]methanone was dissolved in 6 mL of DMF and 200 mg (2.4 mmol) of NaSEt was added. The reaction was heated to 80° C. for 1.5 hours under a nitrogen atmosphere. The reaction mixture quickly filtered over a silica gel column eluted with CHCl3 to remove the solids and exchange the solvent. The effluent from the column was evaporated to a solid and re-dissolved in EtOAc. The EtOAc solution was chromatographed on a silica gel column eluted with a linear gradient beginning with EtOAc-hexane (3:7) and finishing with EtOAc-hexane (1:1). The appropriate fractions were determined by tlc, combined, and evaporated to dryness. This yielded 200 mg of the title compound as a tan amorphous solid.

Workup

addition200 mg (2.4 mmol) of NaSEt was added
filtrationThe reaction mixture quickly filtered over a silica gel column
washeluted with CHCl3
customto remove the solids and exchange the solvent
customThe effluent from the column was evaporated to a solid
dissolutionre-dissolved in EtOAc
customThe EtOAc solution was chromatographed on a silica gel column
washeluted with a linear gradient
customevaporated to dryness

Sources & evidence

ORD record: ord-9a1e1efb439c41e0883ab58132021172
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06432982B1

Reaction notes

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