Sodium Carbonate → HCID 45275880, compound

HRID 1622390Notes

Reaction equation

HRID 1622390 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.[N:18]1[CH:23]=[CH:22][CH:21]=[C:20](B(O)O)[CH: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[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)=[C:2]([C:20]2[CH:19]=[N:18][CH:23]=[CH:22][CH:21]=2)[CH:3]=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

Product 1

HCID 45275880HCID 45275880, compoundYield 25.1%

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), pyridin-3-yl boronic acid (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 (7 mg, 25%), LC-MS (ESI, 3.5 min) Rt 1.06 min, m/z 317 (100%, [M+H]+); m/z (ESI) C16H18ClN4O requires 317.1164 found [M+H]+ 317.1161.

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-7a0e242570144fd4aabf395be72ca614
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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