Sodium Carbonate → HCID 58585876, compound

HRID 1297699Notes

Reaction equation

HRID 1297699 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2Cl)=[O:5])[CH3:2].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.[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>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][C:10]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:9]2[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 58585853HCID 58585853, compound

Product 1

HCID 58585876HCID 58585876, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To the solution of 4-chloro-3-methanesulfonyl-quinoline-6-carboxylic acid ethyl ester (example 61f, 200 mg, 0.64 mmol) in DME (8 mL), phenylboronic acid (116 mg, 0.96 mmol), a catalytical amount of tetrakis(triphenylphosphine)-palladium(0) (147 mg, 0.13 mmol), and sodium carbonate solution (2 M, 1.12 ml, 2.23 mmol) were added. The resulted solution was heated under the microwave irradiation at 150 degrees for 15 min. After cooling to room temperature, the reaction mixture was filtered through a bed of celite with DME. The filtrate was quenched with water, and then extracted with ethyl acetate. The organic layers were collected, washed with brain, dried over sodium sulfate, and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 30%-50% ethyl acetate in hexane in 15 min, then 50% ethyl acetate in hexane in 9 min) afforded 3-methanesulfonyl-4-phenyl-quinoline-6-carboxylic acid ethyl ester (159 mg, 70%). LC-MS m/e 356 (MH+).

Workup

  1. temperatureThe resulted solution was heated under the microwave irradiation at 150 degrees for 15 min
  2. filtrationthe reaction mixture was filtered through a bed of celite with DME
  3. customThe filtrate was quenched with water
  4. extractionextracted with ethyl acetate
  5. customThe organic layers were collected
  6. washwashed with brain
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3395fbef0a0d461ebaf0ee9ac8cfb568
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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