Hydrochloric Acid → Ethyl 5-bromo-2-(cyclopent-1-en-1-yl)-6-(methylsulfonamido)benzofuran-3-carboxylate

HRID 595581Notes

Reaction equation

[NH2:1][C:2]1[C:20]([Br:21])=[CH:19][C:5]2[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:7]([C:9]3[CH2:13][CH2:12][CH2:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[Br:21][C:20]1[C:2]([NH:1][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:3][C:4]2[O:8][C:7]([C:9]3[CH2:13][CH2:12][CH2:11][CH:10]=3)=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[CH:19]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of ethyl 6-amino-5-bromo-2-(cyclopent-1-en-1-yl)benzofuran-3-carboxylate (3.63 g, 10.37 mmol) and pyridine (2.46 g, 31.1 mmol) in DCM (30 mL) was added dropwise methanesulfonyl chloride (2.37 g, 20.7 mmol) at 0° C., then the mixture was stirred at 25° C. overnight. 10% HCl(a.q.) was added, then the mixture was extracted with DCM (50 mL*3), dried over Na2SO4, and concentrated to give the product of ethyl 5-bromo-2-(cyclopent-1-en-1-yl)-6-(methylsulfonamido)benzofuran-3-carboxylate (4.3 g, yield: 96%). 1H-NMR (CDCl3, 400 MHz) δ 8.19 (s, 1H), 7.80 (s, 1H), 7.22 (t, J=2.0 Hz, 1H), 6.84 (s, 1H), 4.45 (q, J=7.2 Hz, 2H), 2.99 (s, 3H), 2.89˜2.94 (m, 2H), 2.62˜2.67 (m, 2H), 2.06 (t, J=7.6 Hz, 2H), 1.47 (t, J=7.2 Hz, 3H). MS (M+H)+: 428/430.

Workup

extractionthe mixture was extracted with DCM (50 mL*3)
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-05195766ce534f80a381c64d1234f5ca
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242998B2

Reaction notes

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