N-bromobutanimide → ethyl 6-bromo-9H-pyrido[3,4-b]indole-3-carboxylate

HRID 1752219Notes

Reaction equation

HRID 1752219 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1[C:14]2[NH:15][C:16]3[C:21]([C:13]=2[CH:12]=[C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:10]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3>C(O)(=O)C>[Br:1][C:19]1[CH:20]=[C:21]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]1[CH:9]=[N:10][C:11]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][C:13]2=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 105078Ethyl Beta-Carboline-3-Carboxylate

Product 1

HCID 13037312ethyl 6-bromo-9H-pyrido[3,4-b]indole-3-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Following a procedure in Chem.Bio.Chem, 2009, 10, 889-895, N-bromosuccinimide (37 mg, 0.208 mmol) was added to a solution of ethyl 9H-pyrido[3,4-b]indole-3-carboxylate (50 mg, 0.208 mmol) in acetic acid (1.5 ml) and stirred at room temperature. After 45 minutes the acetic acid was removed and the solid material was partitioned between EtOAc and NaHCO3. The organic layer was washed with water, brine, and dried over Na2SO4 to afford the desired compound in 98% yield.

Workup

  1. customAfter 45 minutes the acetic acid was removed
  2. customthe solid material was partitioned between EtOAc and NaHCO3
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-9655a9695fd84352900284b4ff82b249
Source dataset
uspto-grants-2015_10
Patent number
US09162980B2

Reaction notes

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