Sodium Carbonate → 4-{3-[(Dimethylamino)sulfonyl]-2-pyridinyl}benzoic acid

HRID 736399Notes

Reaction equation

HRID 736399 reaction equation
Cl[C:2]1[C:7]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:14]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([OH:16])=[O:15].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.CC#N>[CH3:12][N:11]([CH3:13])[S:8]([C:7]1[C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:14]([OH:16])=[O:15])=[CH:18][CH:19]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 122039042-chloro-N,N-dimethyl-3-pyridinesulfonamide

Product 1

HCID 688226564-{3-[(Dimethylamino)sulfonyl]-2-pyridinyl}benzoic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

The product from Example 44A (1.29 g, 5.85 mmol), 4-carboxyphenylboronic acid (0.967 g, 5.82 mmol) and Pd(PPh3)4 (0.337 g, 0.292 mmol) were combined in 1:1 0.5 M Na2CO3:MeCN (46 mL) and heated at 85° C. overnight. The mixture was allowed to cool to room temperature, filtered through celite, and the filtrate was concentrated to 50% volume. The aqueous layer was acidified with concentrated HCl and extracted with CH2Cl2. The organics were dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound as a solid.

Workup

  1. filtrationfiltered through celite
  2. concentrationthe filtrate was concentrated to 50% volume
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-99103ce833b8473fb974a98742616e65
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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