Water → t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrole-1-carboxylate

HRID 13353

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1B(O)O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].O.Br[C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:25]=1[F:31]>C(COC)OC>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:9]2[N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:12]=[CH:11][CH:10]=2)=[C:25]([F:31])[CH:26]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1.6 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid, 200 mg of tetrakistriphenylphosphine palladium, 5 ml of aqueous saturated sodium carbonate solution and 5 ml of water were added in order to a dimethoxyethane (10 ml) solution of 1 g of 4-bromo-3-fluoro-phenylamine, and the reaction liquid was stirred in a nitrogen atmosphere at 70° C. for 3 hours. After cooled, the reaction liquid was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1) to obtain the entitled compound as a pale brown solid.

Workup

customthe reaction liquid
temperatureAfter cooled
customthe reaction liquid
filtrationwas filtered through Celite
additionthe filtrate was diluted with ethyl acetate
washwashed with water and saturated saline in order
dry with materialdried with anhydrous magnesium sulfate
customThe solvent was evaporated away under reduced pressure
customthe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-c32cc0a9d4634d88a4893cadde34f050
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728025B2

Linked notes

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