Sodium Carbonate → HCID 3611076, compound

HRID 2054601Notes

Reaction equation

HRID 2054601 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18](Cl)[N:17]=[C:16](Cl)[CH:15]=1)[CH3:11].C(=O)([O-])[O-].[Na+].[Na+]>CO.C1(C)C=CC=CC=1.[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>[CH2:10]([O:12][C:13](=[O:22])[C:14]1[CH:19]=[C:18]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:17]=[C:16]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:15]=1)[CH3:11]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 948232,6-Dichloro-isonicotinic acid ethyl ester

Product 1

HCID 3611076HCID 3611076, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of phenylboronic acid (915 mg, 7.50 mmol) in methanol (15 mL) was added to a stirred solution of ethyl-2,6-dichloro-isonicotinate (750 mg, 3.41 mmol) and tetrakis-(triphenylphosphine)-palladium(0) (197 mg, 5 mol %) in toluene (60 mL). 2N sodium carbonate (3.41 mL, 6.82 mmol) was added and the reaction was heated to 90° C. (oil bath temp.) for 2-3 hrs until complete (TLC control). The reaction mixture was cooled to room temperature and partitioned between water and diethyl ether. The phases were separated, the aqueous phase being further extracted with diethyl ether (3×30 mL). The combined extract was washed with water and brine. The ethereal solution was dried over anhydrous MgSO4, filtered and concentrated in vacuo to yield the title compound as a white solid (941 mg, 91%); Rf: 0.5 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 8.18 (2H, s, ArH), 8.12 (4H, m, ArH), 7.42 (6H, m, ArH), 4.38 (2H, q, J=7 Hz, CH2O), 1.39 (2H, t, J=7 Hz, CH3)

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. custompartitioned between water and diethyl ether
  3. customThe phases were separated
  4. extractionthe aqueous phase being further extracted with diethyl ether (3×30 mL)
  5. extractionThe combined extract
  6. washwas washed with water and brine
  7. dry with materialThe ethereal solution was dried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-787bc93bd3d34e719240eb3b7aa1f45b
Source dataset
uspto-grants-2008_02
Patent number
US07329680B2

Reaction notes

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