Potassium Carbonate → 2-Methoxy-5-nitro-3-phenylpyridine

HRID 41982

反応式

HRID 41982 の反応式
Br[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1.C1(B2OC(C)(C)[C:22](C)(C)[O:21]2)CC1.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.CO>[CH3:22][O:21][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 866572532-Bromo-5-nitro-3-phenylpyridine

生成物 1

HCID 463150212-Methoxy-5-nitro-3-phenylpyridine収率 60.3%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21867641Toluene methanol溶媒

反応条件

温度
100 °C

実験手順

A mixture of 2-bromo-5-nitro-3-phenylpyridine (0.72 mmol, 0.2 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.86 mmol, 0.16 ml), Pd(PPh3)4 (0.04 mmol, 0.05 g), K2CO3 (2 mmol, 0.28 g) in a toluene/methanol 4:1 mixture (10 ml) was heated at 100° C. for 30 minutes in a microwave, 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 2-methoxy-5-nitro-3-phenylpyridine (0.1 g, yield 55%) of an unexpected 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-ebc150936cc34ef7a10e84ebc7820aa0
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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