Diiodomethane → HCID 90332612, compound

HRID 595584Notes

Reaction equation

[Br:1][C:2]1[C:3]([N:20]([CH3:25])[S:21]([CH3:24])(=[O:23])=[O:22])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH2:14][CH2:13][CH2:12][CH:11]=3)=[C:7]([C:15]([NH:17][CH3:18])=[O:16])[C:6]=2[CH:19]=1.[Zn](CC)[CH2:27]C.C(I)I.[NH4+].[Cl-]>C(Cl)Cl>[C:10]12([C:8]3[O:9][C:5]4[CH:4]=[C:3]([N:20]([CH3:25])[S:21]([CH3:24])(=[O:22])=[O:23])[C:2]([Br:1])=[CH:19][C:6]=4[C:7]=3[C:15]([NH:17][CH3:18])=[O:16])[CH2:27][CH:14]1[CH2:13][CH2:12][CH2:11]2

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-bromo-2-(cyclopent-1-en-1-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (600 mg, 1.40 mmol) and ZnEt2 (15 mL, 14.04 mmol) in DCM (10 mL) was added dropwise CH2I2 (1.2 mL, 14.04 mmol) at 0° C., and then the mixture was stirred at 25° C. After 3 hours, 10 mL NH4Cl (a.q.) was added, and the mixture was extracted with DCM (30 mL*3), and dried over Na2SO4. After concentration, the residue was purified by column chromatography (DCM:EtOAc=3:1) to give the product of 2-(bicyclo[3.1.0]hexan-1-yl)-5-bromo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (300 mg, yield: 48%). 1H-NMR (CDCl3, 400 MHz) δ 8.30 (s, 1H), 7.60 (s, 1H), 6.16 (d, J=2.0 Hz, 1H), 3.34 (s, 3H), 3.12 (d, J=4.8 Hz, 3H), 3.07 (s, 3H), 2.10˜2.21 (m, 2H), 2.01˜2.09 (m, 2H), 1.86˜1.99 (m, 2H), 1.38˜1.46 (m, 1H), 1.37 (d, J=4.0 Hz, 2H). MS (M+H)+: 441/443.

Workup

extractionthe mixture was extracted with DCM (30 mL*3)
dry with materialdried over Na2SO4
concentrationAfter concentration
customthe residue was purified by column chromatography (DCM:EtOAc=3:1)

Sources & evidence

ORD record: ord-2ea5c3d12bd54f7cbf1863186f921534
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242998B2

Reaction notes

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