1H-Indole-4-boronic acid, pinacol ester → 2-(1H-indol-4-yl)-5-(4-(methylsulfonyl)benzyl)-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-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 86670092	—
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-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197986	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 3 using 2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x9, 50 mg, 0.127 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (61.6 mg, 0.253 mmol) and PdCl2(dppf) (4.63 mg, 6.33 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.22 (m, 4 H), 3.48-3.55 (m, 1 H), 3.57-3.68 (m, 1 H), 3.93-4.05 (m, 2 H), 4.07-4.17 (m, 1 H), 4.68-4.79 (m, 3 H), 7.00-7.09 (m, 1 H), 7.21-7.30 (m, 1 H), 7.44-7.50 (m, 1 H), 7.52-7.58 (m, 1 H), 7.60-7.71 (m, 4 H), 7.90-7.98 (m, 2 H), 11.44-11.51 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C25H23N5O3S, 476.17; found 476.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-6b5e0ca84a494aeb90286caa5433655d
Source note	uspto-grants-2015_06