1H-Indole-4-boronic acid, pinacol ester → 2-(1H-indol-4-yl)-5-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Participants

Role	Name	HCID	Charge
Reactant	1H-Indole-4-boronic acid, pinacol ester	HCID 11322471	—
Reactant	2-Chloro-5-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 86670094	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Solvent	Sodium Bicarbonate	HCID 516892	—
Product	2-(1H-indol-4-yl)-5-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197766	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 3 using 2-chloro-5-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x11, 68 mg, 0.179 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (87 mg, 0.357 mmol) and PdCl2(dppf) (6.53 mg, 8.93 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.35-2.41 (m, 3 H), 2.55-2.66 (m, 1 H), 2.68-2.76 (m, 1 H), 2.97-3.09 (m, 1 H), 3.17-3.27 (m, 1 H), 3.82-3.98 (m, 2 H), 4.16-4.27 (m, 1 H), 4.53-4.63 (m, 1 H), 4.57-4.57 (m, 1 H), 7.14-7.24 (m, 1 H), 7.23-7.31 (m, 1 H), 7.38-7.50 (m, 3 H), 7.51-7.63 (m, 3 H), 8.00-8.10 (m, 1 H), 8.48-8.58 (m, 1 H), 11.19-11.35 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H23N5O3S, 462.15; found 462.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-e6fd46a3141045128cb492970637514e
Source note	uspto-grants-2015_06