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

HRID 2267487Notes

Reaction equation

HRID 2267487 reaction equation
[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

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

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 washed with ethyl acetate (2×50 mL) and the combined organic phases were dried and concentrated under reduced pressure to give desired product (685 mg, 58%), which was used in the next step without further purification.

Workup

  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 washed with ethyl acetate (2×50 mL)
  4. customthe combined organic phases were dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1ba85f5ea654462786d697f1bb480105
Source dataset
uspto-grants-2010_12
Patent number
US07858796B2

Reaction notes

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