Potassium Carbonate → 2-Fluoro-4-(2-methoxyphenyl)pyridine

HRID 593279Notes

Reaction equation

HRID 593279 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][N: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.[K+].[K+]>COCCOC.O.C(Cl)Cl.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>[F:1][C:2]1[CH:7]=[C:6]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[O:10][CH3:9])[CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 682877232-Fluoro-4-(2-methoxyphenyl)pyridineYield 55%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolventHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-4-iodo-pyridine (0.5 g, 2.24 mmol) and (2-methoxyphenyl)boronic acid (0.34 g, 2.24 mmol) in DME/water 2:1 (15 mL) was added Pd(PPh3)2Cl2 (20 mg, 0.028 mmol) and K2CO3 (20 mg, 0.15 mmol). The mixture was heated at 80° C. for 6 hours. It was diluted with DCM, washed with water, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, DCM/MeOH 100:0 to 90:10) to give the title compound A3 (0.25 g, 55%). MS (ES) C12H10FNO requires: 203. found: 204 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (silica gel, DCM/MeOH 100:0 to 90:10)

Sources & evidence

ORD record
ord-985344b1ed27457ab992942432ee901d
Source dataset
uspto-grants-2016_01
Patent number
US09242937B2

Reaction notes

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