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

HRID 41978

反応式

HRID 41978 の反応式
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

参加物

6

反応物 4

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

生成物 1

HCID 463150573-Methyl-5-nitro-2-phenylpyridine収率 97%

試薬・触媒・溶媒 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6712a36184ac4dfaa445b8e584cf2b21
出典データセット
uspto-grants-2013_09
特許番号
US08536165B2

関連ノート

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