N-Iodosuccinimide → 6-amino-5-bromo-2-iodo-N-methylbenzofuran-3-carboxamide

HRID 595639Notes

Reaction equation

[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12](=[O:15])[NH:13][CH3:14])=[C:7](B(O)O)[O:8][C:4]=2[CH:3]=1.C1C(=O)N([I:26])C(=O)C1>CC#N>[NH2:1][C:2]1[C:17]([Br:18])=[CH:16][C:5]2[C:6]([C:12]([NH:13][CH3:14])=[O:15])=[C:7]([I:26])[O:8][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of (6-amino-5-bromo-3-(methylcarbamoyl)benzofuran-2-yl)boronic acid (2 g, 6.4 mmol) in MeCN (20 mL) was added NIS (1.44 g, 6.4 mmol) at 0° C., and then the mixture was stirred at 25° C. overnight. After concentrated in vacuum, the residue was purified by column chromatography (DCM:EtOAc=10:1) to give to give pure 6-amino-5-bromo-2-iodo-N-methylbenzofuran-3-carboxamide (2 g, yield: 80%). 1H-NMR (CDCl3, 400 MHz) δ 7.84 (s, 1H), 6.80 (s, 1H), 6.45 (s, 1H), 2.92 (s, 3H). MS (M+H)+: 395/397.

Workup

concentrationAfter concentrated in vacuum
customthe residue was purified by column chromatography (DCM:EtOAc=10:1)
customto give

Sources & evidence

ORD record: ord-e33044d7d7784ed093cbd7b1d6b347d5
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09243002B2

Reaction notes

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