Sodium Carbonate → 1-(3-Chloro-5-phenylpyridin-4-yl)piperidine-4-carboxamide

HRID 1622366Notes

Reaction equation

HRID 1622366 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:17])[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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>[Cl:17][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]=1[N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=[O:15])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

Product 1

HCID 452754591-(3-Chloro-5-phenylpyridin-4-yl)piperidine-4-carboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D (See Example 4) was followed using 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (24 mg, 0.088 mmol), benzene 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 hplc (H2O, MeCN, gradient 90:10 to 10:90 over 30 min) to furnish the title compound as a white solid (6 mg, 22%), LC-MS (ESI) Rt 1.63 min, m/z 316 (100%, [M+H]+); m/z (ESI) C17H18ClN3NaO requires 338.1031 found [M+Na]+ 338.1030.

Workup

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

Sources & evidence

ORD record
ord-52f03979947944e8a8a2c2b6272ad2b1
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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