HCID 86663045, compound → HCID 86663046, compound

HRID 2410799Notes

Reaction equation

HRID 2410799 reaction equation
[N:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:16][CH:15]=2)=[N:12][C:11]([Br:26])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[Br:26][C:11]1[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]2[NH:1][C:15]3[CH:16]=[C:17]([C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])[CH:18]=[CH:19][C:14]=3[C:13]=2[N:12]=1

Participants

3

Reactant 1

HCID 86663045HCID 86663045, compound

Product 1

HCID 86663046HCID 86663046, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of methyl 3-azido-6-bromo-2-(4-(isopropoxycarbonyl)phenyl)-isonicotinate (1.0 g, 2 4 mmol) in 1,2-dichlorobenzene (30 mL) was heated under reflux for 5min. After removal of the solvent under reduced pressure the residue was purified by silica gel chromatography (elution with hexane containing 30% EtOAc) to afford 7-isopropyl 4-methyl 2-bromo-5H-pyrido[3,2-b]indole-4,7-dicarboxylate (0.48 g, 1.20 mmol, 50% yield). MS (ESI) m/z 391.1 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.05 (1H, br. s.), 8.42 (1H, s), 8.33 (1H, d, J=8.24 Hz), 8.01 (1H, d, J=1.22 Hz), 7.91 (1H, d, J=8.24 Hz), 5.22 (1H, quin, J=6.03 Hz), 4.06 (3H, s), 1.39 (6H, d, J=6.10 Hz).

Workup

  1. temperatureunder reflux for 5min
  2. customAfter removal of the solvent under reduced pressure the residue
  3. customwas purified by silica gel chromatography (elution with hexane containing 30% EtOAc)

Sources & evidence

ORD record
ord-bcf2d6c0b6d949ce864c7849b6ec6fcb
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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