Sodium Carbonate → 4-(3-Chloropyridin-2-yl)benzoic acid

HRID 1822930Notes

Reaction equation

HRID 1822930 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)([OH:11])=[O:10].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>[Cl:8][C:7]1[C:2]([C:15]2[CH:16]=[CH:17][C:12]([C:9]([OH:11])=[O:10])=[CH:13][CH:14]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 169882,3-DichloropyridineHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

2,3-Dichloropyridine (2.66 g, 18.0 mmol), 4-carboxyphenylboronic acid (2.70 g, 16.3 mmol), and Pd(PPh3)4 (0.965 g, 0.835 mmol) were combined in a degassed solution of 1:1 0.5M aq Na2CO3:MeCN (120 mL), heated to 85° C. for 5 hours, filtered, and the filtrate concentrated under reduced pressure to remove most of the MeCN. The concentrate was extracted with CH2Cl2 (10 mL) and acidified with 1N HCl. The acidified solution was filtered and the filter cake dried under reduced pressure to provide the title compound as a solid.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customto remove most of the MeCN
  4. extractionThe concentrate was extracted with CH2Cl2 (10 mL)
  5. filtrationThe acidified solution was filtered
  6. customthe filter cake dried under reduced pressure

Sources & evidence

ORD record
ord-e7b8ae9612584c6f990bf780ca589c68
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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