N-bromobutanimide → methyl 3-bromo-6-(methyloxy)-1H-indole-2-carboxylate

HRID 1826223Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([O:14][CH3:15])[CH:8]=2)=[O:4].[Br:16]N1C(=O)CCC1=O>CN(C=O)C>[Br:16][C:13]1[C:12]2[C:7](=[CH:8][C:9]([O:14][CH3:15])=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

2-Methoxycarbonyl-6-methoxy-1H-indole (1.00 g; mfd. by Aldrich) was dissolved in DMF (51.2 mL) under an argon atmosphere, followed by stirring at 0° C. A solution of N-bromosuccinimide (1.02 g) in DMF (21.7 mL) was added dropwise over 30 minutes. The reaction mixture was maintained at 0° C. and stirred for 2.5 hours. The reaction mixture was poured into an ice water. After stirring, the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine, and then dried. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (4:1-3:1 hexane/ethyl acetate) to yield the title compound (760 mg).

Workup

temperatureThe reaction mixture was maintained at 0° C.
stirringstirred for 2.5 hours
stirringAfter stirring
extractionthe resulting mixture was extracted with ethyl acetate
washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and saturated brine
customdried
distillationThe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel column chromatography (4:1-3:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-641a0390e5f04724aac9bb7f90e7d7d7
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07049445B2

Reaction notes

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