Cesium carbonate → HCID 59374125, compound

HRID 473671Notes

Reaction equation

HRID 473671 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.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O>[O:11]1[CH2:12][CH2:13][CH2:14][CH:8]([C:7]2[C:2]([O:28][C:25]3[CH:24]=[CH:23][C:22]([NH:21][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=4)=[CH:27][CH:26]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 212625714-(Pyridin-2-ylamino)phenolHCID 59327121HCID 59327121, compound

Product 1

HCID 59374125HCID 59374125, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-Fluoro-3-(oxepan-4-yl)pyridine (0.061 g, 0.31 mmol), 4-(pyridin-2-ylamino)phenol (0.18 g, 0.94 mmol), and cesium carbonate (0.31 g, 0.94 mmol) were mixed in NMP (0.75 mL). The reaction mixture was placed under a nitrogen atmosphere and stirred at 120° C. for 17 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 to give N-(4-(3-(oxepan-4-yl)pyridin-2-yloxy)phenyl)pyridin-2-amine MS (ESI, pos. ion) m/z: 362.2 (M+1). IC50 (uM) 0.026.

Workup

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

Sources & evidence

ORD record
ord-08b5f15b41ee4fcc8fc0342d34fa69f4
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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