Water → 2-[4-[4-(2-Methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole

HRID 963326

Reaction equation

C([SiH](CC)CC)C.[CH3:8][N:9]1[N:13]=[N:12][C:11]([C:14]2[CH:34]=[C:33]([CH3:35])[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH:22]([C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[CH:28][N:27]=4)O)=[C:16]([CH3:36])[CH:15]=2)=[N:10]1.O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[CH3:8][N:9]1[N:13]=[N:12][C:11]([C:14]2[CH:34]=[C:33]([CH3:35])[C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:24]3[NH:25][C:26]4[C:31]([CH:32]=3)=[CH:30][CH:29]=[CH:28][N:27]=4)=[C:16]([CH3:36])[CH:15]=2)=[N:10]1

Participants

Conditions

Temperature: 20 °C

Procedure

Triethylsilane (5 ml) was added to a stirred solution of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-1-hydroxy-butyl]-7-azaindole (520 mg, 1.33 mmol) in 20 ml of trifluoroacetic acid at 20° C. under nitrogen. The mixture was stirred at 20° C. for 10 min and then stirred at 70°-75° C. for 16 h. To the mixture was added water, and basified with an aqueous sodium bicarbonate solution (to pH=8) followed by extraction with methylene chloride (3×). The combined organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (7.5 cm column, ethyl acetate/hexane, 1/5-8/1). The mixture was recrystallized to afford 349 mg (74%) of 2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole, as a white solid, m.p.147°-150° C.

Workup

stirringstirred at 70°-75° C. for 16 h
extractionfollowed by extraction with methylene chloride (3×)
dry with materialThe combined organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica column chromatography (7.5 cm column, ethyl acetate/hexane, 1/5-8/1)
customThe mixture was recrystallized

Sources & evidence

ORD record: ord-a3305867bc0c49a19a70d575456d0ae2
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05763461

Linked notes

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