methyl 7-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate → HCID 178497039, compound

HRID 2410766Notes

Reaction equation

HRID 2410766 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]=[C:20]([Br:22])[CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:14]=3[NH:15][C:16]=2[CH:17]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O.CCOC(C)=O.CCCCCC>[Br:22][C:20]1[CH:19]=[C:18]([C:23]([O:25][CH3:26])=[O:24])[C:14]2[NH:15][C:16]3[CH:17]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=3[C:13]=2[N:21]=1

Participants

5

Reactant 1

HCID 86663026methyl 7-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate

Product 1

HCID 178497039HCID 178497039, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 6422Trifluoroacetic acidSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 7-(benzyloxy)-2-bromo-5H-pyrido[3,2-b]indole-4-carboxylate (25 mg, 0.061 mmol) in TFA (0.5 mL) was heated at 80° C. for 20 min. The solvent was removed to leave a solid. This was suspended in a mixture of EtOAc and hexane and the solid was collected by filtration to give methyl 2-bromo-7-hydroxy-5H-pyrido[3,2-b]indole-4-carboxylate (10 mg, 0.031 mmol, 51% yield). MS (ESI) m/z 320.9 (M+H). 1H NMR (400 MHz, MeOD) δ ppm 8.03 (1H, d, J=8.56 Hz), 7.79 (1H, s), 6.99 (1H, d, J=1.76 Hz), 6.79 (1H, dd, J=8.56, 2.27 Hz), 4.00-4.07 (3H, m).

Workup

  1. customThe solvent was removed
  2. customto leave a solid
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-556d69a1265346c7b1dffb84599c14f0
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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