Sodium Carbonate → 4-(4-Trifluoromethylphenyl)pyridine

HRID 730311Notes

Reaction equation

HRID 730311 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 6139654-(4-Trifluoromethylphenyl)pyridine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In a 250-mL, round-bottomed flask were added 4-bromopyridine hydrochloride (Aldrich) (4.7 g, 24 mmol), tetrakis (triphenylphosphine) palladium (0) (Aldrich) (1.4 g, 1.2 mmol) and 1,2-dimethoxyethane (120 mL). After stirring under nitrogen for 10 min, a solution of Na2CO3 (5.2 g in 30 mL of water) and 4-trifluoromethylbenzeneboronic acid (5.1 g, 27 mmol) were added sequentially to the mixture. The reaction was stirred in a 90° C. oil bath overnight. The 1,2-dimethoxyethane was evaporated in vacuo, and EtOAc was added to the residue. The aqueous layer was separated and extracted with EtOAc (2×50 mL). The combined EtOAc extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by silica gel flash chromatography using 1:5 EtOAc/hexanes as eluent gave the title compound as a light-tan solid. MS (ESI, pos. ion) m/z: 224 (M+1).

Workup

  1. stirringThe reaction was stirred in a 90° C. oil bath overnight
  2. customThe 1,2-dimethoxyethane was evaporated in vacuo, and EtOAc
  3. additionwas added to the residue
  4. customThe aqueous layer was separated
  5. extractionextracted with EtOAc (2×50 mL)
  6. washThe combined EtOAc extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-3de6c422208a4574a6c4c2ed7cf3bd9b
Source dataset
uspto-grants-2009_09
Patent number
US07582657B2

Reaction notes

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