tert-Butanol → tert-butyl 6-bromo-8-carbamoyl-9H-carbazol-2-ylcarbamate

HRID 2410907Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8](C(O)=O)[CH:7]=[CH:6][C:5]2=1.CC[N:23]([CH2:26]C)CC.P(N=[N+]=[N-])(=O)(OC1C=CC=CC=1)[O:29]C1C=CC=CC=1.[CH3:47][C:48]([OH:51])([CH3:50])[CH3:49]>O1CCOCC1.CO.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15](=[O:17])[NH2:16])[CH:14]=1)[NH:11][C:10]1[CH:9]=[C:8]([NH:23][C:26](=[O:29])[O:51][C:48]([CH3:50])([CH3:49])[CH3:47])[CH:7]=[CH:6][C:5]2=1

Participants

Conditions

Temperature: 55 °C

Procedure

6-Bromo-8-carbamoyl-9H-carbazole-2-carboxylic acid 58D (20 g, 60.0 mmol) was mixed with molecular sieve 4A (20 g, 60.0 mmol) in dioxane (500 mL). To the mixture was added Et3N (20.67 mL, 148 mmol) and diphenyl phosphorazidate (32.1 mL, 148 mmol). The mixture was stirred at 55° C. for 2 hrs. tBuOH (57.4 mL, 600 mmol) was added to the mixture and stirred at 80° C. for 16 hrs. The mixture was diluted with 500 ml MeOH, 500 ml CH2Cl2, and filtered through CELITE®. The filtrate was concentrated to dryness. 100 ml MeOH was added, light brown solid was formed and collected by filtration to give 11.2 g titled product. MS (ESI) m/z 402.1 (M−H)−.

Workup

stirringstirred at 80° C. for 16 hrs
filtrationfiltered through CELITE®
concentrationThe filtrate was concentrated to dryness
addition100 ml MeOH was added
customlight brown solid was formed
filtrationcollected by filtration

Sources & evidence

ORD record: ord-ded164d5ac5846bca291f9b16014571a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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