Hydrogen Peroxide → (3R)-3-[5-(1H-Indol-4-yl)-pyrimidin-2-yloxy]-1-aza-bicyclo[2.2.2]octane 1-oxide

HRID 1441436Notes

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]1[N:15]=[CH:14][C:13]([C:16]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:17]=3[CH:18]=[CH:19][NH:20]4)=[CH:12][N:11]=1)[CH2:2]2.[OH:25]O>>[NH:20]1[C:21]2[C:17](=[C:16]([C:13]3[CH:12]=[N:11][C:10]([O:9][C@@H:3]4[CH:4]5[CH2:5][CH2:6][N+:1]([O-:25])([CH2:8][CH2:7]5)[CH2:2]4)=[N:15][CH:14]=3)[CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19]1

Participants

Reactant 2

HCID 784Hydrogen Peroxide

HCID 112901724-{2-[(3R)-1-azabicyclo[2.2.2]oct-3-yloxy]pyrimidin-5-yl}-1H-indole

Product 1

HCID 11151848(3R)-3-[5-(1H-Indol-4-yl)-pyrimidin-2-yloxy]-1-aza-bicyclo[2.2.2]octane 1-oxide

Procedure

The product of Example 12A (10 mg, 0.03 mol) was oxidized with H2O2 (Aldrich, aq., 30%) according to the procedure of Example 23. The title compound was purified by chromatography [SiO2, CH2Cl2:MeOH (v. 5% NH3.H2O), 90:10]. 1H NMR (300 MHz, CD3OD) δ 2.01-2.32 (m, 3H), 2.42-2.64 (m, 2H), 3.41-3.70 (m, 5H), 3.91-4.24 (m, 1H), 5.39-5.59 (m, 1H), 6.55 (d, J=4.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.23 (t, J=8.0 Hz, 1H), 7.36 (d, J=3.0 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 8.96 (s, 2H) ppm.

Workup

customThe title compound was purified by chromatography [SiO2, CH2Cl2:MeOH (v. 5% NH3.H2O), 90:10]

Sources & evidence

ORD record: ord-27fda662e1014a83b33be42d7e5b8a5f
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655657B2

Reaction notes

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