Cesium carbonate → Tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate

HRID 1778357Notes

Reaction equation

[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14](Br)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:30]([C:32]1[O:33][CH:34]=[CH:35][C:36]=1B1OC(C)(C)C(C)(C)O1)=[O:31].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.C(OCC)(=O)C>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:15]([NH:24][C:25](=[O:28])[CH2:26][OH:27])[C:14]([C:36]3[CH:35]=[CH:34][O:33][C:32]=3[CH:30]=[O:31])=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of tert-butyl 6-(benzenesulfonylmethyl)-3-bromo-2-(2-hydroxyacetylamino)benzoate (Intermediate 36, 0.165 g), 2-formylfuran-3-boronic acid pinacol ester (0.091 g), 1,1′-bis(diphenylphosphino)ferrocene palladium dichloride DCM complex (0.028 g) and cesium carbonate (0.311 g) in THF (4.3 mL) and water (0.7 mL) were sealed, under nitrogen, in a microwave vial and heated in the microwave at 140° C. for 10 minutes. After cooling, the mixture was diluted with ethyl acetate and water and the organic layer was separated, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness to give tert-butyl 6-(benzenesulfonylmethyl)-3-(2-formylfuran-3-yl)-2-(2-hydroxyacetylamino)-benzoate (0.17 g).

Workup

customwere sealed, under nitrogen, in a microwave vial
temperatureAfter cooling
customthe organic layer was separated
washwashed with brine
dry with materialdried (Na2SO4)
filtrationfiltered
customThe filtrate was evaporated to dryness

Sources & evidence

ORD record: ord-f0db9ef8174347119d8834e12899a61b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266896B2

Reaction notes

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