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

HRID 1622367Notes

Reaction equation

HRID 1622367 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.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=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:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=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 201262(4-Methoxyphenyl)boronic acidHCID 28116401-(3,5-Dichloropyridin-4-yl)piperidine-4-carboxamide

Product 1

HCID 451368441-(3-Chloro-5-(4-methoxyphenyl)pyridin-4-yl)piperidine-4-carboxamideYield 30%

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 (24 mg, 0.088 mmol), 4-methoxybenzene boronic acid (16 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 (CH3CN, H2O, 23:77) to furnish the title compound as a white solid (9 mg, 30%), LC-MS (ESI) Rt 1.67 min, m/z 346 (100%, [M+H]+); m/z (ESI) C18H21ClN3O2 requires 346.1317 found [M+H]+ 346.1317.

Workup

  1. customfor 30 min
  2. customThe crude product was purified by preparative hplc (CH3CN, H2O, 23:77)

Sources & evidence

ORD record
ord-bc5f9a3608cc4e3eb1c772a67dacf318
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

Loading…