Water → N-(2-bromo-4-methylsulfonylphenyl)oxolan-3-amine

HRID 575670Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[O:13]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14]1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:18][CH:15]1[CH2:16][CH2:17][O:13][CH2:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-1-fluoro-4-methylsulfonylbenzene (0.8 g, 3.16 mmol), oxolan-3-amine (1.38 g, 15.8 mmol) and K2CO3 (0.87 g, 6.32 mmol) in DMSO (15 mL) was stirred at 100° C. for 5 hrs. It was cooled to r.t. and water (50 mL) was added. The mixture was extracted with EtOAc (50 mL×3) and the combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (PE:EA=50:13:1) to give the title compound (0.7 g, yield: 69.16%). 1H NMR (CDCl3, 400 MHz) δ 8.00 (d, J=1.2 Hz, 1H), 7.74 (d, J=8.8 Hz, 1H), 6.67 (d, J=8.8 Hz, 1H), 5.03 (d, J=6.4 Hz, 1H), 4.23-4.13 (m, 1H), 4.07-3.98 (m, 2H), 3.96-3.87 (m, 1H), 3.83-3.76 (m, 1H), 3.03 (s, 3H), 2.43-2.32 (m, 1H), 1.98-1.88 (m, 1H). LCMS (M+H)+=320.0 (M+H)+, 322.0

Workup

temperatureIt was cooled to r.t.
extractionThe mixture was extracted with EtOAc (50 mL×3)
washthe combined organic layers were washed with brine (50 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (PE:EA=50:13:1)

Sources & evidence

ORD record: ord-c8e1b7c2f3fd4906aee22fa6bf78b15b
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

Loading…