Sodium Carbonate → HCID 45275356, compound

HRID 1622364Notes

Reaction equation

HRID 1622364 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.[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[S:17]1[CH:21]=[CH:20][CH:19]=[C:18]1[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

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275356HCID 45275356, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

General procedure D (See Example 4) was followed using 1-(3-bromopyridin-4-yl)piperidine-4-carboxamide E36 (25 mg, 0.088 mmol), thiophene-2-boronic acid (13 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 (23 mg, 91%), LC-MS (ESI) Rt 1.17 min, m/z 288 (100%, [M+H]+); m/z (ESI) C15H18N3OS requires 288.1165 found [M+H]+ 288.1163.

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-defba4fcc4e4429586623f31d292f170
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…