Sodium Carbonate → 2-Chloro-4-(2-methoxyphenyl)pyridine

HRID 593277Notes

Reaction equation

HRID 593277 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:4]1[CH:3]=[C:2]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[CH:7]=[CH:6][N:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 38477704-Bromo-2-chloropyridine

Product 1

HCID 584326112-Chloro-4-(2-methoxyphenyl)pyridineYield 62.4%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 4-bromo-2-chloro-pyridine (1.5 g, 7.8 mmol) in DME/water/EtOH 5:1:1 (20 mL) was added (2-methoxyphenyl)boronic acid (1.49 g, 9.8 mmol), Pd(PPh3)2Cl2 (112 mg, 0.16 mmol), and Na2CO3 (1.65 g, 15.6 mmol). The mixture was heated at 125° C. for 90 minutes in a microwave oven. It was concentrated under reduced pressure, and the residue was purified by flash chromatography (silica gel, cHex/EtOAc 100:0 to 80:20) to give the title compound A1 (1.07 g, 62%). MS (ES) C12H10ClNO requires: 219. found: 220 (M+H)+.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, cHex/EtOAc 100:0 to 80:20)

Sources & evidence

ORD record
ord-70dd4265c19847c58a7bdafc0b21f239
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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