Sodium Carbonate → HCID 57980135, compound

HRID 1677138Notes

Reaction equation

HRID 1677138 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][O:12][C:13](=[O:14])[C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]([C:8](=[O:10])[CH3:9])=[CH:6][N:7]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 27796981-(6-Chloropyridin-3-yl)ethan-1-one

Product 1

HCID 57980135HCID 57980135, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Procedure U′: To a stirring solution of 1-(6-chloro-pyridin-3-yl)-ethanone (1.0 mmol, CAS #55676-22-7) and 4-methoxycarbonylphenyl boronic acid (1.2 mmol) in dioxane (0.15M), add tetrakis-(triphenylphosphine) palladium (0.044 mmol) and 2M aqueous sodium carbonate (5.0 mmol). Heat the reaction to 90° C. for three hours. After this time, remove the heat and concentrate in vacuo. Purify the title compound via radial chromatography eluting with methanol and dichloromethane. MS (m/e): 256.1 (M+1)

Workup

  1. temperatureHeat
  2. customthe reaction to 90° C. for three hours
  3. customAfter this time, remove the
  4. temperatureheat
  5. concentrationconcentrate in vacuo
  6. customPurify the title compound via radial chromatography
  7. washeluting with methanol and dichloromethane

Sources & evidence

ORD record
ord-4d19dae8ade04a57b737d521798b0756
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

Loading…