Cesium carbonate → 3-[(7-Fluoro-5,5-dioxido-3,4-dihydro-2H-1,5-benzoxathiepin-8-yl)oxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 548654Notes

Reaction equation

F[C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[S:10]([CH:13]1[CH2:17][CH2:16][O:15]C1=O)(=[O:12])=[O:11].[Si]([O:26][CH2:27][C@H:28]([CH3:46])[O:29][C:30]1[CH:31]=[C:32]([CH:42]=[C:43]([OH:45])[CH:44]=1)[C:33]([NH:35][C:36]1[CH:40]=[CH:39][N:38]([CH3:41])[N:37]=1)=[O:34])(C(C)(C)C)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[F:9][C:5]1[C:6]([O:45][C:43]2[CH:42]=[C:32]([CH:31]=[C:30]([O:29][C@@H:28]([CH3:46])[CH2:27][OH:26])[CH:44]=2)[C:33]([NH:35][C:36]2[CH:40]=[CH:39][N:38]([CH3:41])[N:37]=2)=[O:34])=[CH:7][C:2]2[O:15][CH2:16][CH2:17][CH2:13][S:10](=[O:11])(=[O:12])[C:3]=2[CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A solution of 3-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one (126 mg, 0.45 mmol) and 3-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide (203 mg, 0.50 mmol) in acetonitrile (3.5 mL) was treated with caesium carbonate (650 mg, 2.0 mmol) and heated in a microwave reactor at 150° C. for 1.5 hours. The reaction mixture was filtered and concentrated in vacuo. The residue was then chromatographed on silica, eluting with a gradient of 0 to 10% methanol in ethyl acetate, to afford the title compound (78 mg).

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated in vacuo
customThe residue was then chromatographed on silica
washeluting with a gradient of 0 to 10% methanol in ethyl acetate

Sources & evidence

ORD record: ord-69848e2f1b9a41bab56fcd6ae1171ca3
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943607B2

Reaction notes

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