Potassium Carbonate → HCID 86758047, compound

HRID 1934375Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:32].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH+:9]([O-:32])[C:10]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH3:26])[CH2:21][CH2:20]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of Compound B (700 mg, 2.0 mmol) in anhydrous dichloromethane (50 ml) under nitrogen at 0° C., was added 3-chloroperoxybenzoic acid (666 mg, 2.2 mmol) slowly. The resulting solution was allowed to stir for 2 hours at 0° C. and for 0.5 hour at room temperature. To the resulting clear solution potassium carbonate (415 mg, 3.0 mmol) was added, and the reaction mixture was stirred for 0.75 hour. The white precipitate was removed by filtration. The crude product was purified by flash silica gel chromatography (MeOH-CH2Cl2, 10:90 v/v containing 1% NH4OH). After drying, 505 mg of 2-(4-fluorophenyl)-5-(N-ethylpiperidin-4-yl)-3-(4-pyridyl)pyrrole N-oxide was obtained. NMR (CD3OD)σ8.26(d, J=6.27 Hz, 2H), 7.35(m, 2H), 7.26(d, J=6.13 Hz, 2H), 7.11(m, 2H), 6.28(s, 1H), 3.35(m, 6H), 2.85(m, 1H), 2.46(m, 2H), 2.00(m, 2H), 1.39(t, J=7.10 Hz, 3H); MS(ESI)=366.3

Workup

stirringthe reaction mixture was stirred for 0.75 hour
customThe white precipitate was removed by filtration
customThe crude product was purified by flash silica gel chromatography (MeOH-CH2Cl2, 10:90 v/v containing 1% NH4OH)
customAfter drying

Sources & evidence

ORD record: ord-adc403f77d60415192e6336ae7c4bc67
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384052B1

Reaction notes

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