Dichloromethane → 5-Bromo-2-(3-methoxyphenyl)pyridine

HRID 42013

反応式

HRID 42013 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([O:10][CH3:9])[CH:16]=2)=[N:3][CH:4]=1.[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([O:10][CH3:9])[CH:16]=2)=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 693532,5-DibromopyridineHCID 2734370(3-Methoxyphenyl)boronic acid

生成物 2

HCID 153261552-Bromo-5-(3-methoxyphenyl)pyridineHCID 497585195-Bromo-2-(3-methoxyphenyl)pyridine収率 43%

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 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-methoxyphenylboronic acid (2.11 mmol, 0.321 g), PdCl2dppf.DCM (0.21 mmol, 0.172 g), Cs2CO3 (6.33 mmol, 2.063 g) in a dioxane/water 4:1 mixture (14.5 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 5-bromo-2-(3-methoxyphenyl)pyridine (0.242 g, yield 43%) as major product and 2-bromo-5-(3-methoxyphenyl)pyridine (0.039 g) as minor 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-3d31eae132414104885a110c6a7d5294
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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