Sodium Carbonate → 2-p-Tolyl-3-trifluoromethyl-pyridine

HRID 1791233Notes

Reaction equation

HRID 1791233 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.B(O)(O)[C:13]1[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>COC.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>[C:16]1([CH3:19])[CH:17]=[CH:18][C:13]([C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 5898332-Chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 220303732-p-Tolyl-3-trifluoromethyl-pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8254Dimethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a de-gassed mixture of 2-chloro-3-(trifluoromethyl)-pyridine (70.1 mmol), p-tolylboronic acid (70.6 mmol), and 2M Na2CO3 (175.0 mmol), in dimethyl ether (DME; 200 mL) under nitrogen, add Pd(PPh3)4 (2.8 mmol). Stir the mixture at 80° C. overnight, concentrate, and extract with EtOAc. Dry over Na2SO4, concentrate under vacuum, and pass through a silica gel pad to give 2-p-tolyl-3-trifluoromethyl-pyridine.

Workup

  1. concentrationconcentrate
  2. extractionextract with EtOAc
  3. dry with materialDry over Na2SO4
  4. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-eff5ad7dd6fd44f08cb701595aa21c78
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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