Sodium Carbonate → HCID 45274386, compound

HRID 1622397Notes

Reaction equation

HRID 1622397 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6](Br)[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.[C:29](=[O:32])([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>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[CH:3]=[N:4][CH:5]=[C:6]([C:20]3[CH:25]=[CH:24][C:23]([O:32][CH3:29])=[CH:22][CH:21]=3)[C:7]=2[N:8]2[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]2)=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 45275245HCID 45275245, compound

Product 1

HCID 45274386HCID 45274386, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3,5-dibromopyridin-4-yl)piperidine-4-carboxamide E27 (50 mg, 0.14 mmol), 4-methoxyphenylboronic acid (25 mg, 0.15 mmol), tetrakis(triphenylphosphine)palladium(0) (8 mg, 5 mol %), acetonitrile (1.4 mL) and 0.5 M sodium carbonate (0.27 mL, 0.16 mmol) for 30 min. The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 98:2) to furnish the title compound as a white solid (39 mg), LC-MS (ESI, 3.5 min) Rt 1.68 min, m/z 418 (100%, [M+H]+).

Workup

  1. customfor 30 min
  2. customThe crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 98:2)

Sources & evidence

ORD record
ord-a0c0a16dd15e4df0bd75960786321a43
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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