Methyl 3-azido-2-(4-(2-methoxyethoxy)phenyl)-6-(4-methoxyphenyl)isonicotinate → methyl 7-(2-methoxyethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate
Reaction equation
[N:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:16][CH:15]=2)=[N:12][C:11]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[CH3:24][O:23][CH2:22][CH2:21][O:20][C:17]1[CH:16]=[CH:15][C:14]2[C:13]3[N:12]=[C:11]([C:25]4[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=4)[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=3[NH:1][C:19]=2[CH:18]=1Participants
3
Procedure
A solution of methyl 3-azido-2-(4-(2-methoxyethoxy)phenyl)-6-(4-methoxyphenyl)-isonicotinate (42 mg, 0.097 mmol) in 1,2-dichlorobenzene (2 mL) was heated at 160° C. for 10 min. The solvent was removed under a stream of nitrogen and the residue was purified by radial chromatography (step gradient elution with hexane containing 10 to 50% EtOAc) to give methyl 7-(2-methoxyethoxy)-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (28 mg) as a solid. MS (ESI) m/z 407.2 (M+H). 1H NMR (CDCl3) δ ppm 9.38 (1H, s), 8.29 (1H, d, J=8.24 Hz), 8.13 (1H, s), 8.10 (2H, d, J=8.55 Hz), 7.03 (2H, d, J=8.55 Hz), 6.94-7.02 (2H, m), 4.19-4.28 (2H, m), 4.07 (3H, s), 3.88 (3H, s), 3.79-3.84 (2H, m), 3.49 (3H, s).
Workup
- customThe solvent was removed under a stream of nitrogen
- customthe residue was purified by radial chromatography (step gradient elution with hexane containing 10 to 50% EtOAc)
Sources & evidence
- ORD record
- ord-f54b15bbb47b41d4af220d3446d945df
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815840B2
Reaction notes
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