Pyridine → HCID 66693692, 화합물

HRID 2090947노트

반응식

HRID 2090947 반응식
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:5][CH:6]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1B(O)O.N1C=CC=CC=1>CN(C)C(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:5]1[CH:6]=[C:2]([CH3:1])[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4]1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 27339582-Methoxyphenylboronic acidHCID 178470484HCID 178470484, 화합물

생성물 1

HCID 66693692HCID 66693692, 화합물수율 25%

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 31374Dimethylacetamide용매

실험 절차

Ethyl 4-methyl-1H-pyrazole-3-carboxylate (4.0 g) was dissolved in N,N-dimethylacetamide (30 mL), 2-methoxyphenylboronic acid (7.9 g), copper acetate (9.5 g) and pyridine (8.4 mL) were added, and the mixture was stirred at room temperature overnight. The reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL) was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio) to give the title object compound (1.6 g, 25%) as a pale-yellow oil.

후처리

  1. filtrationThe reaction mixture was filtered through celite, 1N hydrochloric acid (50 mL)
  2. additionwas added to the filtrate
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2, volume ratio)

출처 및 근거

ORD 기록
ord-4d2c21dad3f341e89ee71291967cc651
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436043B2

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