Water → HCID 19082065, compound

HRID 53223Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[C:3]1[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]2[N:24]=[N:25][N:26]([CH3:28])[N:27]=2)=[CH:18][C:17]=1[CH3:29].[BH4-].[Na+].O.[OH-].[Na+]>FC(F)(F)C(O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH2:4][CH:3]1[CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[C:17]([CH3:29])=[CH:18][C:19]([C:23]2[N:24]=[N:25][N:26]([CH3:28])[N:27]=2)=[CH:20][C:21]=1[CH3:22]

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 1-methyl-2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-7-azaindole (580 mg, 1.49 mmol) in 16.5 ml of trifluoroacetic acid was added in portions at 0° C. 1.88 g (29.7 mmol) of sodium borohydride. The mixture was stirred at 20° C. for 30 min and then heated at 55°-60° C. for 72 h. To the above mixture was added water, 2N NaOH solution (to pH=8), and the resulting mixture was extracted with methylene chloride. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica column chromatography (10 cm column, methylene chloride/acetone, 30/1-6/1) to yield 193 mg (33%) of 1-methyl-2-[4-[4-(2-methyl-tetrazol-5-yl)-2,6-dimethylphenoxy]-butyl]-2,3-dihydro-7-azaindole, as a solid, m.p. 54°-57° C.

Workup

temperatureheated at 55°-60° C. for 72 h
extractionthe resulting mixture was extracted with methylene chloride
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica column chromatography (10 cm column, methylene chloride/acetone, 30/1-6/1)

Sources & evidence

ORD record: ord-58e716f890514a7398acb9744502eb0d
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618821

Reaction notes

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