Sodium Carbonate → (6-Phenylpyridin-3-yl)acetic acid

HRID 1907906Notes

Reaction equation

HRID 1907906 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC(O)C.O.[OH-].[Na+]>[C:12]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][N:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 140715712-(6-Chloropyridin-3-yl)acetic acid

Product 1

HCID 66718993(6-Phenylpyridin-3-yl)acetic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolventHCID 21889133Propan-2-ol--water (1/1)Solvent2×

Conditions

Temperature
67.5 °C

Procedure

2-chloropyridine-5-acetic acid (0.2 gm, 1.21 mmole), phenylboronic acid (0.16 gm, 1.3 mmole) and 50% water wet 10% Palladium carbon (0.08 gm, 0.036 mmole Pd) were added to 10 ml of 5:1 water isopropanol mixture, then Na2CO3 (0.15 gm, 1.4 mmole) dissolved in 3 ml of water was added to the above mixture, the reaction was heated at 65-70° C. overnight, the reaction was cooled to room temperature, diluted with 20 ml of 70:15:1 i-PrOH/H2O/10% NaOH, filtered, the catalyst was washed with 20 ml×3 using the above mixture, the filtrate was dried under vacuum and crude mixture was used without any purification in the next step.

Workup

  1. additionwas added to the above mixture
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationfiltered
  4. washthe catalyst was washed with 20 ml×3 using the above mixture
  5. customthe filtrate was dried under vacuum and crude mixture
  6. customwas used without any purification in the next step

Sources & evidence

ORD record
ord-06b3892fae0d4ed5808ce15b50a6cb5e
Source dataset
uspto-grants-2013_12
Patent number
US08598169B2

Reaction notes

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