Potassium Carbonate → 2-Chloro-5-(4-methoxyphenyl)pyridine

HRID 1497575Notes

Reaction equation

HRID 1497575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.Br[C:13]1[CH:14]=[CH:15][C:16]([Cl:19])=[N:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[Cl:19][C:16]1[CH:15]=[CH:14][C:13]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:18][N:17]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 201262(4-Methoxyphenyl)boronic acidHCID 27344145-Bromo-2-chloropyridine

Product 1

HCID 121945632-Chloro-5-(4-methoxyphenyl)pyridineYield 88%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A flask was charged with 4-methoxyphenylboronic acid (1.0 g, 6.8 mmol), 5-bromo-2-chloropyridine (1.0 g, 5.2 mmol), Pd(PPh3)4 (50 mg, 0.043 mmol), potassium carbonate (1.08 g, 7.8 mmol), 1,4-dioxane (40 mL) and water (4 mL). The mixture was stirred at 100° C. under Argon for 20 h, and evaporated to afford a crude product. The crude product was purified by chromatography on silica gel (petroleum ether:ethyl acetate=40:1) to give the title compound (1.0 g, 88% yield) as white solids. MS: m/z 220.0 [M+H+].

Workup

  1. customevaporated
  2. customto afford a crude product
  3. customThe crude product was purified by chromatography on silica gel (petroleum ether:ethyl acetate=40:1)

Sources & evidence

ORD record
ord-1b6f23eaff8c40538a241108da7dc49d
Source dataset
uspto-grants-2015_12
Patent number
US09199983B2

Reaction notes

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