Sodium Carbonate → HCID 45275883, compound

HRID 1622393Notes

Reaction equation

HRID 1622393 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.[NH:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]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:21]2[CH:22]=[N:18][NH:19][CH:20]=2)[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 27740104-(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 45275883HCID 45275883, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (24 mg, 0.088 mmol), 1H-pyrazole-4-boronic acid pinacol ester (12 mg, 0.11 mmol), tetrakis(triphenylphosphine)palladium(0) (5 mg, 5 mol %), acetonitrile (1 mL) and 0.5 M sodium carbonate (0.25 mL, 0.12 mmol) for 30 min. The crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 10:1) to furnish the title compound as a white solid (18 mg, 67%), LC-MS (ESI, 3.5 min) Rt 1.06 min, m/z 306 (100%, [M+H]+); m/z (ESI) C14H17ClN5O requires 306.1116 found [M+H]+ 306.1114.

Workup

  1. customfor 30 min
  2. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 10:1)

Sources & evidence

ORD record
ord-505c27ee55814bcfa19f1669be0de003
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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