Sodium Carbonate → HCID 45275355, compound

HRID 1622363Notes

Reaction equation

HRID 1622363 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.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([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:21][CH:20]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275355HCID 45275355, compoundYield 89%

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 (50 mg, 0.17 mmol), 4-methoxyphenylboronic acid (32 mg, 0.21 mmol), tetrakis (triphenylphosphine)palladium(0) (10 mg, 5 mol %), acetonitrile (1.2 mL) and 0.5 M sodium carbonate (0.49 mL, 0.25 mmol) for 50 min. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 97:3 to 95:5) to furnish the title compound as a white solid (49 mg, 89%), LC-MS (ESI) Rt 1.28 min, m/z 312 (100%, [M+H]+); m/z (ESI) C18H22N3O2 requires 312.1706 found [M+H]+ 312.1705.

Workup

  1. customfor 50 min
  2. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, gradient 97:3 to 95:5)

Sources & evidence

ORD record
ord-9bbd3ac816424b62b25e2b0cbe47873e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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