Hydrogen Peroxide → 6-(2-Chlorophenyl)-5-(4-chlorophenyl)-2-[(3,4-difluorobenzyl)oxy]nicotinamide

HRID 916979Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[CH:14][C:11]([C:12]#[N:13])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1.C(O)(C(F)(F)F)=[O:34].[OH-].[K+].OO>O.C(O)C.O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:15]([C:16]2[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[CH:14][C:11]([C:12]([NH2:13])=[O:34])=[C:10]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[C:27]([F:32])[CH:26]=2)[N:9]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To the product of Step D Example 129 (30.0 mg, 0.0516 mmol, material in the TFA salt form) was added 1,4-dioxane (4 mL), ethanol (0.5 mL), KOH (0.272 mg, 4.92 mmol), H2O (0.6 mL) and H2O2 (0.21 g). The reaction was heated to 95° C. for 22 hours. The solution was concentrated and the residue was dissolved in ethyl acetate before washing with water, drying (Na2SO4) and concentrating. The residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel) eluting with 10.5% ethyl acetate/dichloromethane affording the product. MS (electrospray) m/e 485.2 MH+ (Rt=4.2 min LC/MS).

Workup

concentrationThe solution was concentrated
dissolutionthe residue was dissolved in ethyl acetate
washbefore washing with water
dry with materialdrying (Na2SO4)
concentrationconcentrating
customThe residue was purified by preparative thin layer chromatography (20 cm×20 cm, 1000 μm, silica gel)
washeluting with 10.5% ethyl acetate/dichloromethane affording the product

Sources & evidence

ORD record: ord-94f8fbdd9ca34b1fa4f5ea28b171dd76
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07271266B2

Reaction notes

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