HCID 178519991, compound → HCID 178519682, compound

HRID 1793615Notes

Reaction equation

HRID 1793615 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:19][CH:20]=[C:21]([CH:23]([OH:30])[C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)[N:22]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:19][CH:20]=[C:21]([C:23]([C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[O:30])[N:22]=3)=[O:17])=[CH:8]2)=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 178519991HCID 178519991, compound

Product 1

HCID 178519682HCID 178519682, compoundYield 75.6%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(4-chlorobenzyl)-1H-indol-3-yl-[4-(hydroxypyridin-3-yl-methyl)-1H-imidazol-2-yl]methanone (20 mg, 4.5×10−5 mol) in CH2Cl2 (5 mL) was added MnO2 (50 mg). The reaction was stirred for 1 hour at room temperature and filtered through celite to produce the desired product as a white solid (yield 15 mg, 75%). Rf0.5 (ethyl acetate:methanol, 9:1);1H NMR δ 5.61 (s, 2H), 7.36 (m, 6H), 7.61 (m, 1H), 7.68 (m, 1H), 8.28 (s, 1H), 8.39 (m, 1H), 8.60 (d, 1H), 8.86 (d, 1H), 9.16 (s, 1H), 9.40 (s, 1H); ESMS Calcd (C25H17ClN4O2): 440.10, found 441.2 (M+H)+.

Workup

  1. filtrationfiltered through celite

Sources & evidence

ORD record
ord-2308b8a30d7d463382b10ef392265f9a
Source dataset
uspto-grants-2006_07
Patent number
US07081466B2

Reaction notes

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