Diiodomethane → 3-bromo-7-iodo-9H-carbazole-1-carboxamide

HRID 2410918Notes

Reaction equation

N[C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[C:8]([Br:18])[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]=3[NH:12]2)=[CH:4][CH:3]=1.C(I)[I:20].N(OCCC(C)C)=O>[Cu]I>[Br:18][C:8]1[CH:9]=[C:10]([C:15]([NH2:17])=[O:16])[C:11]2[NH:12][C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][CH:3]=[C:2]([I:20])[CH:14]=3

Participants

Conditions

Temperature: 55 °C

Procedure

To a mixture of 7-amino-3-bromo-9H-carbazole-1-carboxamide 470B (1 g, 2.79 mmol) and CH2I2 (15 mL) was slowly added isopentyl nitrite (1 mL, 7.48 mmol). The mixture was heated in microwave at 60° C. for 45 mins copper(I) iodide (0.266 g, 1.397 mmol) was added to the reaction mixture and heated in microwave at 55° C. for additional 30 mins The mixture was concentrated. EtOAc(50 ml) was added and stirred for 10 mins and filtered. The collected solid was washed with H2O 2×50 ml. The remaining solid was purified using preparative HPLC to give titled product. MS (ESI) m/z 412.82 (M−H)−.

Workup

additionwas added to the reaction mixture
concentrationwas concentrated
additionEtOAc(50 ml) was added
filtrationfiltered
washThe collected solid was washed with H2O 2×50 ml
customThe remaining solid was purified

Sources & evidence

ORD record: ord-edbd904c3a0840668fe1d17a5fa76b4a
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

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