Potassium Phosphate, Tribasic → HCID 86728224, compound

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	1-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)	HCID 2773302	—
Reactant	2,6-Dichloro-3-methoxypyridine	HCID 71743336	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 86728224	HCID 86728224	69.8%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a degassed solution of compound 2,6-dichloro-3-methoxypyridine (8.9 g, 0.05 mol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (13 g, 0.05 mol) and K3PO4 (31.8 g, 3.0 mol) in DMF (100 mL) was added Pd(dppf)Cl2 (3.65 g, 5 mmol) under N2. The mixture was heated at 60° C. for about 15 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc and filtered. The filtrate was washed with H2O, brine, dried over Na2SO4. After being concentrated in vacuo, the resulting resulting residue was purified using prep-HPLC to provide the desired product of 2-(6-chloro-3-methoxypyridin-2-yl)-1H-indole (9.0 g, yield: 69.8%). 1H-NMR (CDCl3, 400 MHz) δ 9.52 (s, 1H), 7.65 (d, J=7.6 Hz, 1H), 7.38˜7.43 (m, 2H), 7.07˜7.26 (m, 4H), 4.03 (s, 3H). MS (M+H)+: 259/261.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09265773B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-3f9a02eb11a747078ca15bfd777101a4
Source note	uspto-grants-2016_02