Methyl 3-azido-2,6-bis(4-methoxyphenyl)isonicotinate → methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate

HRID 2410680Notes

Reaction equation

HRID 2410680 reaction equation
[N:1]([C:4]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[N:12][C:11]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]2[C:13]3[N:12]=[C:11]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH:10]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[C:4]=3[NH:1][C:19]=2[CH:18]=1

Participants

3

Reactant 1

HCID 86663006Methyl 3-azido-2,6-bis(4-methoxyphenyl)isonicotinate

Product 1

HCID 66604714methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of methyl 3-azido-2,6-bis(4-methoxyphenyl)isonicotinate (230 mg, 0.589 mmol) in 1,2-dichlorobenzene (5 mL) was heated at 170° C. with gas evolution. After 0.5 hr, the solvent was removed under vacuum and silica gel radial chromatography of the residue (step gradient elution with hexane containing 5 to 20% ethyl acetate) afforded methyl 7-methoxy-2-(4-methoxyphenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (153 mg, 72%) as a yellow solid. MS (ESI) m/z 363.1 (M+H). 1H NMR (CDCl3) δ ppm 9.39 (1H, s), 8.29 (1H, d, J=8.55 Hz), 8.13 (1H, s), 8.10 (2H, d, J=8.85 Hz), 7.03 (2H, d, J=8.85 Hz), 6.93-6.99 (2H, m), 4.07 (3H, s), 3.93 (3H, s), 3.88 (3H, s).

Workup

  1. customthe solvent was removed under vacuum and silica gel radial chromatography of the residue (step gradient elution with hexane containing 5 to 20% ethyl acetate)

Sources & evidence

ORD record
ord-f4fb0eb88d9b439bb51c3f19aad4420d
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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