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

HRID 53222

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 (3x). 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 (3x)
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-bfb4f366bccc4afb8e8ffb785b490cc5
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618821

Linked notes

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