Methyl 3-azido-6-bromo-2-(4-(morpholine-4-carbonyl)phenyl)isonicotinate → methyl 2-bromo-7-(morpholine-4-carbonyl)-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]([C:20]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[CH:16][CH:15]=2)=[N:12][C:11]([Br:28])=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7])=[N+]=[N-]>ClC1C=CC=CC=1Cl>[Br:28][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]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])[CH:18]=[CH:19][C:14]=3[C:13]=2[N:12]=1Participants
Procedure
A solution of methyl 3-azido-6-bromo-2-(4-(morpholine-4-carbonyl)phenyl)-isonicotinate (7.2 g, 16.1 mmol) in 1,2-dichlorobenzene (115 mL) was placed in a 180° C. oil bath and stirred for 10 minutes. The solvent was removed, the residue suspended in methylene chloride, and the solid collected by filtration. This was resuspended in methylene chloride and filtered to afford methyl 2-bromo-7-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxylate (3.02 gm, 45% yield). Removal of the solvent from filtrate followed by flash silica gel chromatography (step gradient elution with methylene chloride containing 0 to 3% MeOH) afforded another 1.02 gm (15% yield) of product. MS (ESI) m/z 416 and 418 (M+H). 1H NMR (MeOD) δ ppm 8.39 (1H, d, J=7.94 Hz), 8.08 (1H, s), 7.78 (1H, s), 7.41 (1H, d, J=7.93 Hz), 4.12 (3H, s), 3.61-3.95 (6H, m), 3.46-3.61 (2H, m).
Workup
- customwas placed in a 180° C.
- customThe solvent was removed
- filtrationthe solid collected by filtration
- filtrationfiltered
Sources & evidence
- ORD record
- ord-9cf1854b8b7b4f52bce923ad3072bfbc
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08815840B2
Reaction notes
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