7-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 2-(7-fluoro-3-methyl-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	7-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole	HCID 68195375	—
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-(7-fluoro-3-methyl-1H-indol-4-yl)-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197877	—

Reaction Steps

The title compound was prepared in a manner similar to EXAMPLE 2 using 2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x9, 66.0 mg, 0.167 mmol), 7-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (92 mg, 0.334 mmol) and PdCl2(dppf) (9.79 mg, 0.013 mmol) in dioxane (1 mL) and aqueous saturated NaHCO3 (0.2 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.93-2.07 (m, 3 H), 2.89-2.99 (m, 1 H), 3.21-3.34 (m, 6 H), 3.47-3.49 (m, 1 H), 3.67-3.72 (m, 1 H), 3.86-3.99 (m, 2 H), 4.35-4.44 (m, 1 H), 4.57-4.64 (m, 2 H), 6.83-6.91 (m, 1 H), 7.02-7.08 (m, 1 H), 7.11-7.17 (m, 1 H), 7.58-7.66 (m, 3 H), 7.87-7.96 (m, 2 H), 11.23-11.30 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C26H26FN5O3S, 508.17; found 508.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-9dfbab22c012407083d912953a5224cd
Source note	uspto-grants-2015_06