Sodium Carbonate → 1-(3-Chloro-5-(2-(methylthio)pyrimidin-5-yl)pyridin-4-yl)piperidine-4-carboxamide
Reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[CH3:18][S:19][C:20]1[N:25]=[CH:24][C:23](B(O)O)=[CH:22][N:21]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(#N)C>[Cl:17][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:23]2[CH:22]=[N:21][C:20]([S:19][CH3:18])=[N:25][CH:24]=2)[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
General procedure E was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide (75 mg, 0.27 mmol), 2-(methylthio)pyrimidine-5-boronic acid (58 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium(0) (16 mg, 5 mol %), acetonitrile (3 mL) and 0.5 M sodium carbonate (0.77 mL, 0.38 mmol). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 25+S) to furnish the title compound as an off white solid (11 mg, 11%), along with recovered 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide as a white solid (41 mg, 55% RSM), LC-MS (ESI, 4 min) Rt 2.14 min, m/z 364 (100%, [M+H]+); m/z (ESI) C16H18N5OSCl requires 363.09206, found [M+H]+ 363.0922.
Workup
- customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 96:4-82:18, biotage 25+S)
Sources & evidence
- ORD record
- ord-4b47a76f09c84c31b75ca5a2ae7dcec1
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778925B2
Reaction notes
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