N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methanesulfonamide → N-{6-[2-(2-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methanesulfonamide
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=CC=CC=1C1CCC2C(=CC=C(OC3N=CC(N)=CC=3)C=2)O1>>[F:29][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:17][C:18]3[N:23]=[CH:22][C:21]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:20][CH:19]=3)[CH:13]=2)[O:8]1Participants
3
Procedure
N-{6-[2-(2-Fluorophenyl)chroman-6-yloxy]pyridin-3-yl}methanesulfonamide was prepared as described for N-[6-(2-phenylchroman-6-yloxy)pyridin-3-yl]methane sulfonamide in Example 46 starting from 400 mg of 6-[2-(2-fluorophenyl)chroman-6-yloxy]-pyridin-3-ylamine (Example 51). The product was crystallised from a mixture of methanol and diethyl ether. 1H NMR (400 MHz, d6-DMSO) δ: 9.67 (s, 1H), 7.99 (d, 1H, J 2.8 Hz), 7.67 (dd, 1H, J 8.8, 2.8 Hz), 7.55 (m, 1H), 7.42 (m, 1H), 7.29-7.23 (m, 2H), 6.98 (dd, 1H, J 8.8 Hz), 6.92-6.84 (m, 3H), 5.35 (dd, 1H, J 10.4, 2.3 Hz), 3.01 (m, 1H), 2.99 (s, 3H), 2.76 (m, 1H), 2.16 (m, 1H), 2.04 (m, 1H).
Workup
- customThe product was crystallised from a mixture of methanol and diethyl ether
Sources & evidence
- ORD record
- ord-b38b082407d645569d3f69111fe8d6d5
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425568B2
Reaction notes
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