Sodium Carbonate → HCID 45275780, compound

HRID 1622382Notes

Reaction equation

HRID 1622382 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.[CH:17]1(B(O)O)[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH:17]1([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)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275780HCID 45275780, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (25 mg, 0.088 mmol), cyclopropyl boronic acid (9.4 mg, 0.44 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 tlc on silica (CH2Cl2, MeOH 10:1) to furnish the title compound as a white solid (4 mg, 19%), LC-MS (ESI, 3.5 min) Rt 0.97 min, m/z 246 (100%, [M+H]+); m/z (ESI) C14H19N3O requires 246.1601 found [M+H]+ 246.1596.

Workup

  1. customfor 50 min
  2. customThe crude product was purified by preparative tlc on silica (CH2Cl2, MeOH 10:1)

Sources & evidence

ORD record
ord-fbb8e9222d384187ab17560dd1b29282
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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