Sodium Carbonate → HCID 45275673, compound

HRID 1622377Notes

Reaction equation

HRID 1622377 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][N:19]1[C:23]([CH3:24])=[C:22](B2OC(C)(C)C(C)(C)O2)[C:21]([CH3:34])=[N:20]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:22]2[C:21]([CH3:34])=[N:20][N:19]([CH3:18])[C:23]=2[CH3:24])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27953111,3,5-Trimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

Product 1

HCID 45275673HCID 45275673, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure E was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (75 mg, 0.27 mmol), 1,3,5-trimethyl-1H-pyrazole-4-boronic pinacol ester (65 mg, 0.27 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, 94:6-80:20, biotage 25+S) to furnish the title compound as a very pale yellow solid (34 mg, 35%), along with recovered 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide (52 mg, 57% RSM), LC-MS (ESI, 4 min) Rt 1.55 min, m/z 348 (100%, [M+H]+); m/z (ESI) C17H22N5OCl requires 347.1513, found [M+H]+ 347.1508.

Workup

  1. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, EtOH, 94:6-80:20, biotage 25+S)

Sources & evidence

ORD record
ord-8c8604bec26b4b1e98fdfc5ad8028b96
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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