tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate → 5-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide

HRID 1806202

反応式

HRID 1806202 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([Br:26])[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]1)=[O:3]>CO.Cl.O1CCOCC1>[Br:26][C:6]1[CH:7]=[C:8]2[C:12](=[C:4]([C:2]([NH2:1])=[O:3])[CH:5]=1)[NH:11][CH:10]=[C:9]2[CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

参加物

5

反応物 1

HCID 59600660tert-butyl 4-(5-bromo-7-carbamoyl-1H-indol-3-yl)piperidine-1-carboxylate

生成物 1

HCID 113247225-bromo-3-(4-piperidinyl)-1H-indole-7-carboxamide収率 58%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of 1,1-dimethylethyl 4-[7-(aminocarbonyl)-5-bromo-1H-indol-3-yl]-1-piperidinecarboxylate (1.56 g, 3.7 mmol) in methanol (10 mL), HCl in dioxane (4M, 35.5 mL) was added. The reaction mixture was stirred at room temperature for 2 hours. The solvent was evaporated under reduced pressure and the resulting residue was partitioned between ethyl acetate (50 mL) and 5% of aqueous NaOH (50 mL). The aqueous layer was washed with ethyl acetate (2×50 mL) and the combined organic phases were dried with MgSO4 and concentrated under reduced pressure to give the desired product (685 mg, 58%), which was used in the next step without further purification.

後処理

  1. customThe solvent was evaporated under reduced pressure
  2. customthe resulting residue was partitioned between ethyl acetate (50 mL) and 5% of aqueous NaOH (50 mL)
  3. washThe aqueous layer was washed with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic phases were dried with MgSO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-63be934521964d489fc04777936cd90a
出典データセット
uspto-grants-2013_01
特許番号
US08354406B2

関連ノート

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