HCID 86591895, compound → methyl 6-(tert-butoxycarbonylamino)-1H-indole-2-carboxylate

HRID 1883117Notes

Reaction equation

[N:1](/[C:4](=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:12][CH:11]=1)/[C:5]([O:7][CH3:8])=[O:6])=[N+]=[N-]>C1(C)C=CC=CC=1>[C:20]([O:19][C:17]([NH:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[NH:1]2)=[CH:11][CH:12]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 80 °C

Procedure

851 mg (2.67 mmol) of methyl (2E)-2-azido-3-{4-[(tert-butoxycarbonyl)amino]phenyl}prop-2-enoate was dissolved in 40 mL toluene. The mixture was heated to 80° C. for 2 h, cooled, and concentrated. Purification by column chromatography, eluting with 25% ethyl acetate/hexane provided 551 mg of methyl 6-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate as a yellow solid.

Workup

temperaturecooled
concentrationconcentrated
customPurification by column chromatography
washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record: ord-b98e54655be64c1baec08e58365c567f
Source dataset: uspto-grants-2004_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06759428B2

Reaction notes

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