Cesium carbonate → HCID 118021853, compound

HRID 518527Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]3[CH:22]=[CH:21][O:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[O:31][CH:32]([F:34])[F:33].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:33][CH:32]([F:34])[O:31][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][O:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]3[CH:22]=[CH:21][O:20][C:14]=3[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A capped mixture of 4-(3-hydroxy-5-methylsulfonylphenyl)-6-methylfuro[2,3-c]pyridin-7-one (25 mg, 0.08 mmol), 1-(bromomethyl)-2-(difluoromethoxy)benzene (28 mg, 0.12 mmol), and Cs2CO3 (50 mg, 0.15 mmol) in DMF (900 uL) was heated to 80° C. for 3 h. The mixture was filtered and the filter cake was washed with ACN (500 uL), the filtrate was purified by prep-HPLC to afford the title compound (22 mg, 58%) as a white solid. LCMS (M+H)+=476.

Workup

filtrationThe mixture was filtered
washthe filter cake was washed with ACN (500 uL)
customthe filtrate was purified by prep-HPLC

Sources & evidence

ORD record: ord-c53cb4fc21cb4b0d9936f4e7c72faa87
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115114B2

Reaction notes

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