Dichloromethane → HCID 22032933, compound

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-Benzyl-5-Bromo-1H-Indole	HCID 285756	—
Reactant	3-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)	HCID 2734660	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	HCID 22032933	HCID 22032933	41.2%

Reaction Steps

1-Benzyl-5-(3-chloro-4-fluorophenyl)-1H-indole was prepared by coupling 1-benzyl-5-bromo-1H-indole (1.46 g, 5.10 mmol), and 3-chloro-4-fluorophenylboronic acid (1.08 g, 6.19 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.209 g, 0.256 mmol), potassium carbonate (1.44 g, 10.4 mmol) in dioxane (51 mL) and water (5 mL), following the procedure described in Step 1 of Example 11. Purification by flash chromatography (Biotage apparatus) using hexane as an eluant and drying 60° C. furnished the title compound as a light brown gum (0.706 g, 41%). 1HNMR (200 MHz, DMSO-d6) δ 7.8-7.9 (m, 2H), 7.6-7.7 (m, 1H), 7.4-7.6 (m, 3H), 7.15-7.4 (m, 6H), 6.55 (d, 1H, J=2.5 Hz), and 5.45 ppm (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07368471B2
Source dataset	uspto-grants-2008_05
ORD ID	ord-f6140383dab14d7e96a14136495ba2ea
Source note	uspto-grants-2008_05