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

HRID 71669ノート

反応式

HRID 71669 の反応式
[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]

参加物

7

反応物 5

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 64246602-Bromo-5-bromomethylpyridineHCID 178439317HCID 178439317、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-89fafad7b60e47069de4377772e61fc5
出典データセット
uspto-grants-2014_09
特許番号
US08822522B2

反応ノート

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