N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamide → N-{6-[2-(3-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide
Reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:29]C1C=C(C2CCC3C(=CC=C(OC4N=CC(N)=CC=4)C=3)O2)C=CC=1>>[F:29][C:3]1[CH:2]=[C:1]([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]4[N:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=4)[CH:13]=3)[O:8]2)[CH:6]=[CH:5][CH:4]=1Participants
3
Procedure
N-{6-[2-(3-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methane sulfonamide was prepared as described for N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamide in Example 46 starting from 300 mg of 6-[2-(3-fluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine (Example 54). The product was purified by passing through silica gel using ethyl acetate-heptane (5:1) as an eluant. 1H NMR (400 MHz, d6-DMSO) δ: 9.67 (s, 1H), 7.99 (dd, 1H, J 2.8, 0.6 Hz), 7.67 (dd, 1H, J 8.8, 2.8 Hz), 7.46 (m, 1H), 7.31-7.27 (m, 2H), 7.17 (m, 1H), 6.98 (dd, 1H, J 8.8, 0.6 Hz), 6.90-6.88 (m, 3H), 5.16 (dd, 1H, J 10.0, 2.2 Hz), 2.99 (s, 3H), 2.96 (m, 1H), 2.72 (m, 1H), 2.20 (m, 1H), 1.99 (m, 1H).
Workup
- customThe product was purified
Sources & evidence
- ORD record
- ord-3d6089bccec3409fa3ff78f8cf29ad53
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425568B2
Reaction notes
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