Sodium Carbonate → 4-[6-(Ethylsulfonyl)-3-pyridinyl]-2-fluorobenzoic acid

HRID 1867856Notes

Reaction equation

HRID 1867856 reaction equation
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][N:7]=1)(=[O:5])=[O:4])[CH3:2].[C:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][C:17]=1[F:25])([OH:15])=[O:14].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1>[CH2:1]([S:3]([C:6]1[N:7]=[CH:8][C:9]([C:19]2[CH:20]=[CH:21][C:16]([C:13]([OH:15])=[O:14])=[C:17]([F:25])[CH:18]=2)=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27632014-Carboxy-3-fluorophenylboronic acidHCID 589514652-Ethanesulfonyl-5-iodo-pyridine

Product 1

HCID 579801154-[6-(Ethylsulfonyl)-3-pyridinyl]-2-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Procedure VV: To a stirring solution of 2-Ethanesulfonyl-5-iodo-pyridine (1.0 mmol) and (4-carboxy-3-fluorophenyl)boronic acid (1.3 mmol) in dioxane (0.1M), add dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium dichloromethane complex (0.03 mmol) and 2M aqueous sodium carbonate (3.0 mmol). Heat the reaction to reflux for 4 hours. After this time, remove the heat and concentrate in vacuo. Wash with dichloromethane while extracting with water. Acidify the aqueous layer with 1N hydrochloric acid and extract with 10% isopropanol/dichloromethane four times. Combine the organics, dry with sodium sulfate, decant and concentrate in vacuo. MS (m/e): 310.3 (M+1)

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureto reflux for 4 hours
  4. customAfter this time, remove the
  5. temperatureheat
  6. concentrationconcentrate in vacuo
  7. washWash with dichloromethane
  8. extractionwhile extracting with water
  9. extractionextract with 10% isopropanol/dichloromethane four times
  10. dry with materialCombine the organics, dry with sodium sulfate
  11. customdecant
  12. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-3fc476b9e64b411abe5dd097772ed24c
Source dataset
uspto-grants-2009_12
Patent number
US07632857B2

Reaction notes

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