Hydrochloric Acid → 5-Bromo-6-fluoro-indole-1-carboxylic acid tert-butyl ester

HRID 49512Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[F:11])[NH:7][CH:6]=[CH:5]2.CC([O-])(C)C.[K+].[C:18]([O:22][C:23](=O)[O:24]C(C)(C)C)([CH3:21])([CH3:20])[CH3:19].Cl>CN(C=O)C.O>[C:18]([O:22][C:23]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[C:10]([F:11])[CH:9]=2)[CH:5]=[CH:6]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2.1 g (9.81 mmol) 5-Bromo-6-fluoro-indole in 35 ml of DMF were added 1.54 g (13.76 mmol) KOtBu and 3.0 g (13.76 mmol) Di-tert.butylcarbonate, and the solution was stirred for 1 hr at room temperature and 30 min at 60° C. The mixture was poured into water, acidified with 2M aqueous HCl and extracted with Et2O. Drying of the organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with hexane/EtOAc 49:1 gave 2.6 g (84%) 5-Bromo-6-fluoro-indole-1-carboxylic acid tert-butyl ester as a colorless liquid, MS: 313 (M, 1Br).

Workup

extractionextracted with Et2O
dry with materialDrying of the organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with hexane/EtOAc 49:1

Sources & evidence

ORD record: ord-1df8e36785a24267ad3d14e98b8a8277
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706751B2

Reaction notes

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