Sodium Carbonate → HCID 58378290, compound

HRID 1622389Notes

Reaction equation

HRID 1622389 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:16])[C:7]=1[N:8]1[CH2:12][CH2:11][CH:10]([C:13]([NH2:15])=[O:14])[CH2:9]1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=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:16][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)[C:7]=1[N:8]1[CH2:12][CH2:11][CH:10]([C:13]([NH2:15])=[O:14])[CH2:9]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 45275137HCID 45275137, compound

Product 1

HCID 58378290HCID 58378290, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

General procedure D was followed using 1-(3,5-dichloropyridin-4-yl)pyrrolidine-3-carboxamide E21 (23 mg, 0.088 mmol), 4-methoxybenzene 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 tlc on silica gel (CH2Cl2, MeOH, 10:1) to give impure title compound as a white solid (15 mg). Further purification by preparative hplc (H2O, MeCN, gradient 90:10 to 10:90 over 30 min) furnished the title compound as a white solid, LC-MS (ESI, 3.5 min) Rt 1.40 min, m/z 332 (100%, [M+H]+); m/z (ESI, 3.5 min) C17H18ClN3NaO2 requires 354.0980 found [M+Na]+ 354.0980

Workup

  1. customfor 30 min
  2. customThe crude product was purified by preparative tlc on silica gel (CH2Cl2, MeOH, 10:1)

Sources & evidence

ORD record
ord-1d54dfb52d3e4accb034fadd4db4b195
Source dataset
uspto-grants-2014_07
Patent number
US08778925B2

Reaction notes

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