Sodium Carbonate → HCID 45275781, compound

HRID 1622383Notes

Reaction equation

HRID 1622383 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[NH:17]1[CH:21]=[C:20](B(O)O)[CH:19]=[N:18]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>[NH:17]1[CH:21]=[C:20]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)[CH:19]=[N:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 177502781H-Pyrazole-4-boronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275781HCID 45275781, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (25 mg, 0.088 mmol), 1H-pyrazol-4-boronic acid pinnacol ester (21 mg, 0.11 mmol), tetrakis(triphenylphosphine)palladium(0) (5 mg, 5 mol %), 0.5 M sodium carbonate (0.25 mL, 0.12 mmol) and acetonitrile (1 mL) for 50 min. The crude product was purified by preparative hplc (H2O, MeCN, 95:5) to furnish the title compound as a white solid (11 mg, 46%), m/z (ESI) C14H18N5O requires 272.1506 found [M+H]+272.1509.

Workup

  1. customfor 50 min
  2. customThe crude product was purified by preparative hplc (H2O, MeCN, 95:5)

Sources & evidence

ORD record
ord-23061e0ad3d14333b8ccf339f9a9c63a
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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