N-bromobutanimide → 1-BOC-5-bromomethyl-7-nitro-indole-2-carboxylic acid methyl ester

HRID 336457Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH3:14])=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])=[O:4].[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([CH2:14][Br:25])=[CH:9][C:8]=2[N+:15]([O-:17])=[O:16])=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

1-BOC-5-methyl-7-nitro-indole-2-carboxylic acid methyl ester (34 g, 101.7 mmol) prepared in Step A was dissolved in carbon tetrachloride (100 mL). N-bromosuccinimide (27.2 g, 152.6 mmol) and AIBN (1.7 g, 10.2 mmol) were added thereto, and the mixture was stirred for 5 h at 80° C. After completion of the reaction, the reaction mixture was distilled under reduced pressure, and purified by column chromatography to give the title compound (48.0 g, Yield 100%).

Workup

customAfter completion of the reaction
distillationthe reaction mixture was distilled under reduced pressure
custompurified by column chromatography

Sources & evidence

ORD record: ord-7f1cf2ab05e04e028e781f655f9dee92
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889691B2

Reaction notes

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