cis-N-{4-[(6-bromopyridin-3-yl)oxy]tetrahydrofuran-3-yl}propane-2-sulfonamide → cis-N-[4-(4-bromophenoxy)tetrahydrofuran-3-yl]propane-2-sulfonamide
Reaction equation
[Br:1][C:2]1N=[CH:6][C:5]([O:8][C@H:9]2[CH2:13][O:12][CH2:11][C@H:10]2[NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[CH:4][CH:3]=1.[CH3:21]S(O[C@H]1[C@H](OC2C=CC(Br)=CC=2)COC1)(=O)=O>>[Br:1][C:2]1[CH:21]=[CH:6][C:5]([O:8][C@H:9]2[CH2:13][O:12][CH2:11][C@H:10]2[NH:14][S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[CH:4][CH:3]=1Participants
Procedure
The title compound was prepared according to the general procedure for the synthesis of cis-N-{4-[(6-bromopyridin-3-yl)oxy]tetrahydrofuran-3-yl}propane-2-sulfonamide in Preparation 1, except that trans-4-(4-bromophenoxy)tetrahydrofuran-3-yl methanesulfonate was used in place of trans-4-[(6-bromopyridin-3-yl)oxy]tetrahydrofuran-3-yl methanesulfonate, and the chromatographic purification was carried out with a gradient of 15% to 35% acetone in heptane. Yield: 238 mg, 0.65 mmol, 31%. 1H NMR (400 MHz, CDCl3) δ 1.30 (d, J=6.8 Hz, 3H), 1.33 (d, J=6.8 Hz, 3H), 3.11 (septet, J=6.8 Hz, 1H), 3.66 (dd, J=9.1, 8.4 Hz, 1H), 3.89 (dd, J=10.7, 1.7 Hz, 1H), 4.07-4.13 (m, 2H), 4.19 (m, 1H), 4.71 (m, 1H), 5.12 (d, J=9.6 Hz, 1H), 6.75 (d, J=9.0 Hz, 2H), 7.36 (d, J=9.0 Hz, 2H).
Workup
- customthe chromatographic purification
Sources & evidence
- ORD record
- ord-7ed5a809e160466dae2201e9a0d64508
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08278457B2
Reaction notes
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