Hydrogen Bromide → 1H-Pyrazole-5-carboxylic acid, 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl ester

HRID 646644ノート

反応式

HRID 646644 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][C:10](OS(C3C=CC=CC=3)(=O)=O)=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[BrH:28].C(=O)([O-])O.[Na+]>C(O)(=O)C>[Br:28][C:10]1[CH2:11][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 86600833ethyl 1-(3-chloro-2-pyridinyl)-4,5-dihydro-3-[(phenylsulfonyl)oxy]-1H-pyrazole-5-carboxylate

生成物 1

HCID 100653831H-Pyrazole-5-carboxylic acid, 3-bromo-1-(3-chloro-2-pyridinyl)-4,5-dihydro-, ethyl ester収率 85%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of ethyl 1-(3-chloro-2-pyridinyl)-4,5-dihydro-3-[(phenylsulfonyl)oxy]-1H-pyrazole-5-carboxylate (i.e. the product of Step A) (1.0 g, 2.44 mmol) in acetic acid (4 mL) was added to a solution of hydrogen bromide in acetic acid (33%, 1.2 g, 4.89 mmol). After about 1 h the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution (100 mL). The mixture was then extracted with ethyl acetate (2×50 mL), and the combined extracts were dried (MgSO4) and evaporated to provide the title product as an oil (0.69 g, 85% yield), which slowly crystallized. The 1H NMR spectrum was the same as reported for the product of Example 1, Step C.

後処理

  1. extractionThe mixture was then extracted with ethyl acetate (2×50 mL)
  2. dry with materialthe combined extracts were dried (MgSO4)
  3. customevaporated

出典と根拠

ORDレコード
ord-1995a83dc79a44ad8bb587a12e964764
出典データセット
uspto-grants-2010_04
特許番号
US07705160B2

反応ノート

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