Hydrogen Peroxide → HCID 59177837, compound

HRID 423677Notes

Reaction equation

HRID 423677 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[O:28][N:27]=[C:26]([CH:29]([CH3:31])[CH3:30])[N:25]=3)[CH2:20][CH2:19]2)=[CH:12][N:11]=1.[OH:32]O>FC(F)(F)C(O)C(F)(F)F>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:9])=[O:32])[CH:5]=[CH:4][C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[O:28][N:27]=[C:26]([CH:29]([CH3:31])[CH3:30])[N:25]=3)[CH2:20][CH2:19]2)=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 66673097HCID 66673097, compound

Product 1

HCID 59177837HCID 59177837, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

The title compound (109 g, 76%) was prepared as a white solid from 2-[2-fluoro-4-(methylthio)phenyl]-5-[({1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl)oxy]pyridine (prepared as in Step 2, 138 g, 312 mmol), 30% H2O2 (aq) (41 mL, 410 mmol) and 1,1,1,3,3,3-hexafluoro-2-propanol (400 mL) in a manner similar to Example 171, Step 3. 1H NMR (400 MHz, CDCl3): δ 8.39 (d, 1H, J=2.8 Hz), 8.13 (t, 1H, J=7.8 Hz), 7.77 (dd, 1H, Ja=8.7 Hz, Jb=1.9 Hz), 7.50 (dd, 1H, Ja=10.4 Hz, Jb=1.6 Hz), 7.43 (dd, 1H, Ja=8.1 Hz, Jb=1.7 Hz), 7.26 (d, 1H, J=3.0 Hz), 4.27-4.16 (m, 2H), 3.92 (d, 2H, J=6.2 Hz), 3.20-3.00 (m, 2H), 2.87 (septet, 1H, J=7.0 Hz), 2.74 (s, 3H), 2.15-2.03 (m, 1H), 2.00-1.90 (m, 2H), 1.52-1.40 (m, 2H), 1.27 (d, 6H, J=7.0 Hz); LRMS (ESI), m/z 459 (M+H).

Sources & evidence

ORD record
ord-2eb2efadd54d4700be6bff932a1ee150
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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