Sodium Carbonate → HCID 45275573, compound

HRID 1622373Notes

Reaction equation

HRID 1622373 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.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][C:19]=1[CH3:27].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>[F:17][C:18]1[CH:23]=[CH:22][C:21]([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:20][C:19]=1[CH3:27]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 45275354HCID 45275354, compound

Product 1

HCID 45275573HCID 45275573, compoundYield 56%

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), 4-fluoro-3-methylphenylboronic acid (16 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 tlc (CH2Cl2, MeOH, 10:1) to furnish the title compound as a white solid (15 mg, 56%), LC-MS (ESI 3.5 min) Rt 1.46 min, m/z 314 (100%, [M+H]+); m/z (ESI) C18H21FN3O requires 314.1663 found [M+H]+ 314.1658.

Workup

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

Sources & evidence

ORD record
ord-27124212cb2748b39b8359ee21a2b06e
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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