Dimethylformamide → 1-(6-Bromopyridin-3-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 71669노트

반응식

HRID 71669 반응식
[CH2:1]([C:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:6][N:5]=1)[CH2:2][CH3:3].[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.C([O-])(O)=O.[Na+]>C(OCC)C>[CH2:12]([O:11][C:9]([C:7]1[CH:8]=[C:4]([CH2:1][CH2:2][CH3:3])[N:5]([CH2:21][C:18]2[CH:17]=[N:16][C:15]([Br:14])=[CH:20][CH:19]=2)[N:6]=1)=[O:10])[CH3:13]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 64246602-Bromo-5-bromomethylpyridineHCID 178439317HCID 178439317, 화합물

생성물 1

HCID 581029001-(6-Bromopyridin-3-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Ethyl 3-n-propylpyrazole-5-carboxylate (1.7 g, 9.1 mmol), 2-bromo-5-bromomethylpyridine (4.6 g, 9.1 mmol) and potassium carbonate (1.8 g, 12.7 mmol) were dissolved in DMF (70.0 mL, 904 mmol). The resulting suspension was stirred at room temperature overnight. The material was diluted with aqueous. NaHCO3 and diethyl ether. The aqueous layer was further extracted with diethyl ether. The combined organics were dried over MgSO4, filtered and concentrated. The residue was purified using flash chromatography [1st 30:1 hexanes/EtOAc; 2nd 10:1 hexanes/EtOAc]. The two isomers were separated and analyzed by NMR and NOE: 1-(6-bromopyridin-3-ylmethyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (1.2 g) and 2-(6-bromopyridin-3-ylmethyl)-5-propyl-2H-pyrazole-3-carboxylic acid ethyl ester.

후처리

  1. additionThe material was diluted with aqueous
  2. extractionThe aqueous layer was further extracted with diethyl ether
  3. dry with materialThe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customThe two isomers were separated

출처 및 근거

ORD 기록
ord-89fafad7b60e47069de4377772e61fc5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822522B2

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