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

HRID 562014

Reaction equation

HRID 562014 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 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.

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 was washed with ethyl acetate (2×50 mL)
  4. dry with materialthe combined organic phases were dried with MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81de9dc539a348ed9ee8b40082110f29
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Linked notes

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