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

HRID 41982

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HRID 41982 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 463150212-Methoxy-5-nitro-3-phenylpyridine수율 60.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 21867641Toluene methanol용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebc150936cc34ef7a10e84ebc7820aa0
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536165B2

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