Dichloromethane → 3-Bromo-5-(3-methoxyphenyl)pyridine

HRID 1970960Notes

Reaction equation

HRID 1970960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](Br)[CH:18]=1.C(Cl)Cl>COCCOC.C(=O)([O-])[O-].[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:18]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 693693,5-DibromopyridineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 529371443-Bromo-5-(3-methoxyphenyl)pyridine

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 3-methoxy-phenylboronic acid (1.0 eq, 300 mg, 1.27 mmol) in DME (3 ml) and 2M sodium carbonate solution (1.2 ml) under an inert atmosphere of argon is treated with 3,5-dibromopyridine (300 mg, 1.27 mmol) followed by PdCl2(dppf).DCM (0.1 eq, 93 mg) and then is heated using microwave radiation at 90° C. for 30 minutes. The mixture is extracted with DCM and the organic extracts are washed with water. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with 0-30% EtOAc in iso-hexane to afford the title compound [M+H]+=265.

Workup

  1. customat 90° C.
  2. customfor 30 minutes
  3. extractionThe mixture is extracted with DCM
  4. washthe organic extracts are washed with water
  5. customThe solvent is removed in vacuo
  6. customthe crude product is purified by chromatography on silica eluting with 0-30% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-39bc28ca1f7d4ad38c1a7c71ce2165dd
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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