Cesium carbonate → HCID 59327038, compound

HRID 410318Notes

Reaction equation

[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)=[O:11].[O:19]=[S:20]1(=[O:33])[CH2:25][CH2:24][CH:23]([C:26]2[C:27](F)=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:27]2[C:26]([CH:23]3[CH2:24][CH2:25][S:20](=[O:33])(=[O:19])[CH2:21][CH2:22]3)=[CH:31][CH:30]=[CH:29][N:28]=2)=[CH:14][CH:13]=1)=[O:11]

Participants

Conditions

Temperature: 200 °C

Procedure

A mixture of (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.485 g, 2.035 mmol), 3-(1,1-dioxidotetrahydro-2H-thiopyran-4-yl)-2-fluoropyridine (0.311 g, 1.356 mmol), and cesium carbonate (1.326 g, 4.07 mmol) in NMP (5 mL) in a sealed tube was heated at 200° C. in 2 h. The reaction mixture was cooled, taken in H2O, filtered the dark brown solid, purified by ISCO (50% EtOAc/Hexanes) to give the expected product as a tan solid. MS (ESI, pos. ion) m/z: 448.1 (M+1). IC50 (uM) +++++.

Workup

temperatureThe reaction mixture was cooled
filtrationfiltered the dark brown solid
custompurified by ISCO (50% EtOAc/Hexanes)

Sources & evidence

ORD record: ord-0ad7006e00024bcebc6db8f63e5d40f9
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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