3-Fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenol → 4-(4-Fluorophenyl)-2-[[3-fluoro-5-(3,4,5,6-tetrahydro-4-methoxy-2H-pyran-4-yl)phenoxy)methyl]-5-(4-(methylsulfonyl)phenyl)oxazole

HRID 890868Notes

Reaction equation

HRID 890868 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]4([O:37][CH3:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:26]=3)[O:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[F:39]C1C=C(C2(OC)CCOCC2)C=C(O)C=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH2:23][O:24][C:25]3[CH:26]=[C:27]([C:31]4([O:37][CH3:38])[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:28]=[C:29]([F:39])[CH:30]=3)[O:11][C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 117362763-Fluoro-5-(4-methoxytetrahydro-2H-pyran-4-yl)phenolHCID 129861254-(4-Fluorophenyl)-5-(4-(methylsulfonyl)phenyl)-2-[[3-(3,4,5,6-tetrahydro-4-methoxy-2H-pyran-4-yl)phenoxy)methyl]oxazole

Product 1

HCID 99375694-(4-Fluorophenyl)-2-[[3-fluoro-5-(3,4,5,6-tetrahydro-4-methoxy-2H-pyran-4-yl)phenoxy)methyl]-5-(4-(methylsulfonyl)phenyl)oxazole

Procedure

4-(4-Fluorophenyl)-2-[[3-fluoro-5-(3,4,5,6-tetrahydro-4-methoxy-2H-pyran-4-yl)phenoxy)methyl]-5-(4-(methylsulfonyl)phenyl)oxazole was prepared in a similar fashion from the reaction of the mesylate (Example 2, Step 4) and 4-(3-fluoro-5-hydroxyphenyl)-4-methoxy-3,4,5,6-tetrahydro-2H-pyran: 1H-NMR (CDCl3, 300 MHz) δ 1.84–2.02 (m, 4H), 2.98 (s, 3H), 3.08 (s, 3H), 3.81 (m, 4H), 5.23 (s, 2H), 6.76 (m, 2H), 6.92 (s, 1H), 7.13 (m, 2H), 7.60 (m, 2H), 7.79 (d, 2H, J=8.5 Hz) and 7.93 (d, 2H, J=8.5 Hz). 19F-NMR (CDCl3, 280 MHz) δ −110.8 and −111.7. Anal. Calc'd. for C29H27NO6F2: C, 62.69; H, 4.90; N, 2.52. Found: C, 62.53; H, 4.96; N, 2.51.

Sources & evidence

ORD record
ord-55f74fec5027420e93deda0709b49d1f
Source dataset
uspto-grants-2006_02
Patent number
US06998415B2

Reaction notes

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