HCID 15326267, compound → 5-bromo-3-(N-methylpyrrolidin-3-yl)1H-indole

HRID 964757Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[C:16](=O)[N:15]([CH3:18])[C:13](=O)[CH2:12]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:12][CH2:13][N:15]([CH3:18])[CH2:16]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 3-(5-bromo-1H-indol-3-yl)-N-methylsuccinimide (1.3 g, 4.23 mmol) in anhydrous tetrahydrofuran (12 mL) at 0° C., was added lithium aluminum hydride (1M solution in tetrahydrofuran, 9.3 mL, 9.3 mmol). The resulting mixture was heated to reflux under argon for 2 hours, then cooled to 0° C. and quenched with cold water (2 mL) and ammonium hydroxide (15 mL). The resulting solution was stirred at room temperature for 1 hour and then filtered through celite. The filtrate was evaporated to dryness and the crude product extracted into ethyl acetate (250 mL). The solvent was once again evaporated and the product purified by silica gel chromatography using chloroform/ammonia(2M in methanol) (9:1) as the eluent to provide the title compound as a white solid (0.700 g, 64%). m.p. 152°-154° C.; HRMS (FAB): MH+ for C13H1579BrN2, calculated 279.0496, found 279.0478.

Workup

temperatureThe resulting mixture was heated
temperatureto reflux under argon for 2 hours
customquenched with cold water (2 mL) and ammonium hydroxide (15 mL)
filtrationfiltered through celite
customThe filtrate was evaporated to dryness
extractionthe crude product extracted into ethyl acetate (250 mL)
customThe solvent was once again evaporated
customthe product purified by silica gel chromatography

Sources & evidence

ORD record: ord-516adb17e09f46cb925ade311432ea86
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770742

Reaction notes

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