Cesium carbonate → HCID 46214545, compound

HRID 410248Notes

Reaction equation

F[C:2]1[C:7]([CH:8]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([O:32][C:2]2[C:7]([CH:8]3[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:28][CH:27]=1)=[O:25]

Participants

Conditions

Temperature: 140 °C

Procedure

2-Fluoro-3-(oxepan-4-yl)pyridine (0.10 g, 0.51 mmol), (1H-benzo[d]imidazol-2-yl)(4-hydroxyphenyl)methanone (0.37 g, 1.54 mmol), and cesium carbonate (0.50 g, 1.54 mmol) were mixed in NMP (1.5 mL). The reaction mixture was placed under a nitrogen atmosphere and stirred at 140° C. for 96 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with 1 M aqueous sodium hydroxide, washed with sat. sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography (EtOAc/hexanes) to give (1H-benzo[d]imidazol-2-yl)(4-(3-(oxepan-4-yl)pyridin-2-yloxy)phenyl)methanone. MS (ESI, pos. ion) m/z: 414.1 (M+1). IC50 (uM) +++++.

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc (2×)
washThe combined organic layers were washed with 1 M aqueous sodium hydroxide
washwashed with sat. sodium chloride
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe resulting crude product was purified by silica gel chromatography (EtOAc/hexanes)

Sources & evidence

ORD record: ord-6f8b314ca6ad41ee8ad3251e7337a816
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759532B2

Reaction notes

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