Sodium Carbonate → 1-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2,3,4-Trifluorobenzeneboronic acid	HCID 2783280	—
Reactant	5-Bromo-1-(1-methylethyl)-1H-indole-3-carboxaldehyde	HCID 5050377	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	1-(propan-2-yl)-5-(2,3,4-trifluorophenyl)-1H-indole-3-carbaldehyde	HCID 86685273	83.8%

Reaction Conditions

Temperature	80 °C

Reaction Steps

Sodium carbonate (0.188 mL, 2M, 0.376 mmol) was added to a stirred room temperature solution of 5-bromo-1-(propan-2-yl)-1H-indole-3-carbaldehyde (50 mg, 0.188 mmol), 2,3,4-trifluorophenylboronic acid (66 mg, 0.376 mmol) and PdCl2(dppf) (13.7 mg, 0.019 mmol) in DMF (1.0 mL) and the reaction mixture was stirred at 80° C. for 12 hours. The reaction mixture was cooled to room temperature, partitioned between ethyl acetate (2×15 mL) and water (10 mL), washed with saturated sodium bicarbonate (10 mL), brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (50 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08742110B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-910940917b6342969e7c05a6841a63c2
Source note	uspto-grants-2014_06