2-(Pyridin-2-yl)ethyl methanesulfonate → 1-[3-[3-(4-Fluoro-phenyl)-butoxy]-4-methoxy-5,6-dimethyl-2-(2-pyridin-2-yl-ethoxy)-phenyl]-ethanone

HRID 219450Notes

Reaction equation

HRID 219450 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:26])[CH2:9][CH2:10][O:11][C:12]2[C:13]([OH:25])=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([CH3:21])=[C:16]([CH3:20])[C:17]=2[O:18][CH3:19])=[CH:4][CH:3]=1.CS(O[CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=1)(=O)=O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:26])[CH2:9][CH2:10][O:11][C:12]2[C:13]([O:25][CH2:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[C:14]([C:22](=[O:24])[CH3:23])[C:15]([CH3:21])=[C:16]([CH3:20])[C:17]=2[O:18][CH3:19])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 226370342-(Pyridin-2-yl)ethyl methanesulfonateHCID 595834961-{3-[3-(4-Fluoro-phenyl)-butoxy]-2-hydroxy-4-methoxy-5,6-dimethyl-phenyl}-ethanone

Product 1

HCID 252542221-[3-[3-(4-Fluoro-phenyl)-butoxy]-4-methoxy-5,6-dimethyl-2-(2-pyridin-2-yl-ethoxy)-phenyl]-ethanoneYield 43%

Procedure

Example 4e (100 mg, 0.28 mmol) was reacted with 2-pyridin-2-ylethyl methanesulfonate (1.6 eq.) as described under General Procedure F to give the title compound (56 mg, 43%). 1H NMR (300 MHz, CDCl3) δ 8.51 (d, J=4.2 Hz, 1H), 7.57 (dt, J=7.7, 1.8 Hz, 1H), 7.19-7.09 (m, 4H), 6.96-6.91 (m, 2H), 4.34 (t, J=6.6 Hz, 2H), 3.83 (t, J=6.6 Hz, 2H), 3.73 (s, 3H), 3.11 (6.6 Hz, 2H), 2.99-2.92 (m, 1H), 2.26 (s, 3H), 2.07 (s, 3H), 2.00 (s, 3H), 1.95-1.88 (m, 2H), 1.25 (d, J=7.0 Hz, 3H).

Sources & evidence

ORD record
ord-290cac3268ed40958321f673dcf0486a
Source dataset
uspto-grants-2012_06
Patent number
US08202513B2

Reaction notes

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