Sodium Bicarbonate → 3-bromo-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole

HRID 1787575ノート

反応式

HRID 1787575 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:8](C(O)=O)=[C:9]2[CH2:14][CH2:13][CH2:12][N:10]2[N:11]=1.C(=O)(O)[O-].[Na+].[Br:23]NC(=O)CCC(N)=O>CN(C=O)C.O.C(OCC)(=O)C>[Br:23][C:8]1[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:11][N:10]2[CH2:12][CH2:13][CH2:14][C:9]=12

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 9834204N-BromosuccinamideHCID 597100292-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic Acid

生成物 1

HCID 597100253-bromo-2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole収率 70.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Stir a mixture of 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (Preparation 2C; 2 g, 8.7 mmol), sodium bicarbonate (3.3 g, 38.4 mmol), and N-bromosuccinamide (1.7 g, 9.6 mmol) in DMF (50 mL) at room temperature for 2 h. Dilute the crude mixture with water (50 mL) and ethyl acetate (100 mL). Separate the ethyl acetate layer, extract with saturated sodium chloride solution, dry over anhydrous sodium sulfate, filter, and evaporate to a solid mass. Purify by MPLC (SiO2, 1:1 ethyl acetate/hexane) to obtain 1.62 g (70%) of the title compound as a cream solid. MS (ES) m/z 264 (M+H).

後処理

  1. customSeparate the ethyl acetate layer
  2. extractionextract with saturated sodium chloride solution
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. customevaporate to a solid mass
  6. customPurify by MPLC (SiO2, 1:1 ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-3e9fe18969784c3d98b1483d8da8d936
出典データセット
uspto-grants-2009_03
特許番号
US07511056B2

反応ノート

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