Potassium Carbonate → 6-fluoro-1-(2-fluorophenyl)-3-{2-[(2S)-oxiran-2-yl]ethyl}-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide

HRID 2237507Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[S:9](=[O:19])(=[O:18])[NH:8][CH2:7][C:6]=2[CH:20]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][C@@H:30]1[O:32][CH2:31]1>CC(C)=O.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[S:9](=[O:19])(=[O:18])[N:8]([CH2:28][CH2:29][C@H:30]3[CH2:31][O:32]3)[CH2:7][C:6]=2[CH:20]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A solution 6-fluoro-1-(2-fluorophenyl)-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.13 g, 0.29 mmol) in acetone (3 mL) was treated with potassium carbonate (0.11 g, 0.81 mmol), (S)-(−)-4-Bromo-1,2-epoxybutane (0.14 mL, 1.41 mmol) and was heated to 45° C. for two h then at room temperature for 14 h. The reaction mixture was diluted with ethyl ether (40 mL) and washed with sat. sodium bicarbonate (2×20 mL), the organic layer was isolated, dried with MgSO4 and evaporated. The crude reaction product was purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane) to provided 6-fluoro-1-(2-fluorophenyl)-3-{2-[(2S)-oxiran-2-yl]ethyl}-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.17 g, 67%) as a white solid.

Workup

washwashed with sat. sodium bicarbonate (2×20 mL)
customthe organic layer was isolated
dry with materialdried with MgSO4
customevaporated
customThe crude reaction product
customwas purified by flash chromatography (SiO2, 3-50% ethyl acetate/heptane)

Sources & evidence

ORD record: ord-8e6ccfc5a97b41d5a75b69b47a31e6a4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718652B2

Reaction notes

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