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

HRID 41989노트

반응식

HRID 41989 반응식
Cl[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.[CH:17]1(B2OC(C)(C)C(C)(C)O2)[CH2:19][CH2:18]1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[CH:17]1([C:2]2[C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][C:5]([N+:14]([O-:16])=[O:15])=[CH:4][N:3]=2)[CH2:19][CH2:18]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 27580152-Cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 463146982-Chloro-5-nitro-3-phenylpyridine2회

생성물 1

HCID 673947372-Cyclopropyl-5-nitro-3-phenylpyridine수율 17.5%

시약·촉매·용매 1

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

실험 절차

In a schlenck tube, a mixture of 2-chloro-5-nitro-3-phenylpyridine (described in Intermediate 3 (step B)) (1.43 mmol, 0.4 g), 2-cyclopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.59 mmol, 0.29 ml), PdCl2dppf.DCM (0.14 mmol, 0.12 g), Cs2CO3 (4.3 mmol, 1.4 g) in a dioxane/water 4:1 mixture (6.5 ml) was heated at 100° C. for 16 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 2-cyclopropyl-5-nitro-3-phenylpyridine (0.06 g, 17% of yield) of the expected 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-362a057819524af3a914f50bf55d8af3
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536165B2

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