Cesium carbonate → HCID 59373979, compound

HRID 473655Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

2-Fluoro-3-(tetrahydro-2H-pyran-3-yl)pyridine (0.10 g, 0.55 mmol), 4-(pyridin-2-ylamino)phenol (0.26 g, 1.38 mmol), and cesium carbonate (0.54 g, 1.66 mmol) were mixed in NMP (2 mL). The reaction mixture was placed under a nitrogen atmosphere and stirred at 120° C. for 16 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 (1×), sat. sodium chloride (1×), dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to give N-(4-(3-(tetrahydro-2H-pyran-3-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine. MS (ESI, pos. ion) m/z: 348.1 (M+1). IC50 (uM) 0.012.

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 (1×), sat. sodium chloride (1×)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record: ord-c387a5b9e7e946d3afd6f57b4e4b800c
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637500B2

Reaction notes

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