Methyl 3-azido-6-(3-fluoro-4-methoxyphenyl)-2-(4-(methoxycarbonyl)phenyl)isonicotinate → dimethyl 2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4,7-dicarboxylate

HRID 2410741Notes

Reaction equation

HRID 2410741 reaction equation
[N:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:15]=2)=[N:12][C:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([F:32])[CH:25]=2)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[F:32][C:26]1[CH:25]=[C:24]([C:11]2[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]3[NH:1][C:15]4[CH:16]=[C:17]([C:20]([O:22][CH3:23])=[O:21])[CH:18]=[CH:19][C:14]=4[C:13]=3[N:12]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH3:31]

Participants

3

Reactant 1

HCID 86663018Methyl 3-azido-6-(3-fluoro-4-methoxyphenyl)-2-(4-(methoxycarbonyl)phenyl)isonicotinate

Product 1

HCID 66605908dimethyl 2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4,7-dicarboxylateYield 77.6%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of methyl 3-azido-6-(3-fluoro-4-methoxyphenyl)-2-(4-(methoxycarbonyl)phenyl)isonicotinate (1.06 g, 2.43 mmol) in 1,2-dichlorobenzene (30 mL) was heated under reflux for 5 minutes. Removal of the solvent followed by flash silica gel chromatography (elution with hexane containing 15% EtOAc) afforded dimethyl 2-(3-fluoro-4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4,7-dicarboxylate (0.77 gm). MS (ESI) m/z 409.1 (M+H). 1H NMR (DMSO-d6) δ ppm 11.86 (1H, br. s.), 8.29-8.47 (3H, m), 8.11 (1H, dd, J=13.12, 2.14 Hz), 7.97-8.06 (1H, m), 7.92(1H, d, J=8.24 Hz), 7.32 (1H, t, J=8.85 Hz), 4.09 (3H, s), 3.95 (3H, s), 3.94 (3H, s).

Workup

  1. temperatureunder reflux for 5 minutes
  2. customRemoval of the solvent
  3. washfollowed by flash silica gel chromatography (elution with hexane containing 15% EtOAc)

Sources & evidence

ORD record
ord-5fef230ce2504accb9f8d8df02d11e92
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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