HCID 178519991, compound → HCID 178519682, compound

HRID 352154Notes

Reaction equation

HRID 352154 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 75.4%

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, 4.51×10−5 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%). Rf 0.5 (ethyl acetate:methanol, 9:1); 1H NMR δ5.61 (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-22e7f79d04cf464abf46475c7f440861
Source dataset
uspto-grants-2004_06
Patent number
US06743919B2

Reaction notes

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