Pyridine → 6-Methoxy-3-(6-methoxy-2-naphthyl)-1-methyl-1H-indazole

HRID 1061853Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=2)[CH:13]=1)=O.[CH3:24][NH:25][NH2:26].N1C=CC=CC=1>CN(C)C1C=CN=CC=1.O>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3]([C:10]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[CH:15][CH:16]=[C:17]([O:22][CH3:23])[CH:18]=4)[CH:13]=3)=[N:26][N:25]2[CH3:24])=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2-fluoro-4-methoxyphenyl)(6-methoxy-2-naphthyl)methanone (1.0 g, 3.22 mmol), 1-methylhydrazine (0.74 g, 16.1 mmol), pyridine (10 mL), and 4-dimethylaminopyridine (0.39 g, 3.22 mmol) was stirred at 100° C. for 12 h. The mixture poured in the water, extracted with ethyl ether, washed with HCl (2N), and dried over MgSO4. Evaporation and crystallization from ethyl ether/hexanes gave an off-white solid (0.82 g, 80% yield, m.p. 166-168° C.); MS m/e 319 (M+H)+.

Workup

extractionextracted with ethyl ether
washwashed with HCl (2N)
dry with materialdried over MgSO4
customEvaporation and crystallization from ethyl ether/hexanes

Sources & evidence

ORD record: ord-033fd77463074b29a77bb36cc6fae111
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06960607B2

Reaction notes

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