Acetonitrile → HCID 45274287, compound

HRID 1622396Notes

Reaction equation

HRID 1622396 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:16])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1.C(=O)([O-])[O-].[Na+].[Na+].[C:23](#N)[CH3:24]>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>[Cl:16][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:24]2[CH:23]=[CH:6][CH:7]=[CH:2][CH:3]=2)[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 45275464HCID 45275464, compound

Product 1

HCID 45274287HCID 45274287, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

General procedure D was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carbonitrile E48 (100 mg, 0.39 mmol), phenyllboronic acid (57 mg, 0.47 mmol), tetrakis(triphenylphosphine)palladium(0) (22 mg, 5 mol %), 0.5 M sodium carbonate (1.1 mL, 0.55 mmol) and acetonitrile (3.5 mL) for 45 min. The crude product was purified by preparative hplc (H2O, MeCN, 90:10-10:90, 30 min) to furnish the title compound (25 mg, 22%), LC-MS (ESI, 3.5 min) Rt 2.24 min, m/z 298 (100%, [M+H]+).

Workup

  1. customfor 45 min
  2. customThe crude product was purified by preparative hplc (H2O, MeCN, 90:10-10:90, 30 min)

Sources & evidence

ORD record
ord-d99fa72f7f5444579a7bd023f7066b5c
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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