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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 453201Generated: October 25, 2026

4-Bromobutyryl chloride → 5-{6-[(4-Bromo-butyrylamino)-methyl]-pyrimidin-4-yloxy}-indole-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

https://huagongshe.com/reaction/453201

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Bromobutyryl chlorideHCID 70225—
ReactantDiisopropylethylamineHCID 81531—
Reactant5-(6-Aminomethyl-pyrimidin-4-yloxy)-indole-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amideHCID 59394236—
SolventDichloromethaneHCID 6344—
SolventEthyl AcetateHCID 8857—
Product5-{6-[(4-Bromo-butyrylamino)-methyl]-pyrimidin-4-yloxy}-indole-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amideHCID 59394487—

Reaction Steps

5-(6-Aminomethyl-pyrimidin-4-yloxy)-indole-1-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide (52.5 mg, 0.117 mmol) is dissolved in DCM (5 mL) at 0° C. DIEA (0.025 mL, 0.143 mmol) is added followed by 4-bromo-butyryl chloride (0.020 mL, 0.172 mmol). The reaction is stirred for 30 min before being diluted with ethyl acetate and washed with water. The organic layer is removed, dried, and concentrated to provide the title compound. MS (ESI) m/z 595.6 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08492393B2
Source datasetuspto-grants-2013_07
ORD IDord-fe7475cc3fac43028a383b89710058b1
Source noteuspto-grants-2013_07