2-(Pyridin-2-yl)ethyl methanesulfonate → 1-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-2-methyl-6-(2-pyridin-2-yl-ethoxy)-phenyl]-ethanone

HRID 219451Notes

Reaction equation

HRID 219451 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([C:23](=[O:25])[CH3:24])[C:5]([OH:22])=[C:6]([O:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])[C:7]=1[O:8][CH3:9].CS(O[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)(=O)=O>>[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([C:23](=[O:25])[CH3:24])[C:5]([O:22][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)=[C:6]([O:10][CH2:11][CH2:12][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH3:14])[C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 226370342-(Pyridin-2-yl)ethyl methanesulfonateHCID 595835101-{3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-6-hydroxy-4-methoxy-2-methyl-phenyl}-ethanone

Product 1

HCID 252526851-[3-Chloro-5-[3-(4-fluoro-phenyl)-butoxy]-4-methoxy-2-methyl-6-(2-pyridin-2-yl-ethoxy)-phenyl]-ethanoneYield 89%

Procedure

Example 7c (500 mg, 1.31 mmol) was reacted with 2-pyridin-2-ylethyl methanesulfonate (2.0 eq.) as described under General Procedure F to give the title compound as an oil (410 mg, 89%). 1H NMR (300 MHz, CDCl3) δ 8.52 (d, J=4.1 Hz, 1H), 7.58 (dt, J=7.7, 1.8 Hz, 1H), 7.17-7.10 (m, 4H), 6.97-6.90 (m, 2H), 4.37 (t, J=6.6 Hz, 2H), 3.85 (t, J=6.6 Hz, 2H), 3.81 (s, 3H), 3.10 (t, J=6.5 Hz, 2H), 2.98-2.91 (m, 1H), 2.26 (s, 3H), 2.14 (s, 3H), 1.96-1.88 (m, 2H), 1.25 (d, J=7.0 Hz, 3H). MS (ES+) m/z 485.9 (M+H+).

Sources & evidence

ORD record
ord-ffea8deb750f493b822213990e80712e
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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