Dichloromethane → 3-Methyl-5-nitro-2-phenylpyridine

HRID 41978

Reaction equation

HRID 41978 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[CH3:8][C:7]1[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:3][CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 52004662-Bromo-3-methyl-5-nitropyridine

Product 1

HCID 463150573-Methyl-5-nitro-2-phenylpyridineYield 97%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In a schlenck tube, a mixture of 2-bromo-3-methyl-5-nitropyridine (4.6 mmol, 1.0 g), phenylboronic acid (4.6 mmol, 0.560 g), PdCl2dppf.DCM (0.47 mmol, 0.4 g), Cs2CO3 (13.8 mmol, 4.5 g) in a dioxane/water 4:1 mixture (18 ml) was heated at 100° C. for 14 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 3-methyl-5-nitro-2-phenylpyridine (0.95 g, yield 97%) as major product.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-6712a36184ac4dfaa445b8e584cf2b21
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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