Potassium Carbonate → 6-Bromo-2-(1-(5-fluoropyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole
Reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[S:8][C:4]=2[CH:3]=1.Cl[C:19]1[N:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([O:9][CH:10]3[CH2:11][CH2:12][N:13]([C:19]4[N:24]=[CH:23][C:22]([F:25])=[CH:21][N:20]=4)[CH2:14][CH2:15]3)[S:8][C:4]=2[CH:3]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 6-bromo-2-(piperidin-4-yloxy)benzo[d]thiazole (1 g, 3.19 mmol) and 2-chloro-5-fluoropyrimidine (0.508 g, 3.83 mmol) in DMF (15 mL) was added potassium carbonate (1.32 g, 9.58 mmol). The reaction mixture was stirred at 100° C. for 4 h. The reaction mixture was cooled to rt, diluted with water (40 mL), and extracted with EtOAc (3×20 mL). The combined organic layers were dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 40% EtOAc) to afford 6-bromo-2-(1-(5-fluoropyrimidin-2-yl)piperidin-4-yloxy)benzo[d]thiazole (1.112 g, 2.72 mmol, 85% yield) as a white solid.
Workup
- temperatureThe reaction mixture was cooled to rt
- extractionextracted with EtOAc (3×20 mL)
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 40% EtOAc)
Sources & evidence
- ORD record
- ord-6122de807b7843da9c5993a6556ef689
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940716B2
Reaction notes
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