7-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 2-(7-fluoro-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-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole	HCID 68194891	—
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-1H-indol-4-yl)-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197983	—

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, 90 mg, 0.228 mmol), 7-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (119 mg, 0.456 mmol) and PdCl2(dppf) (8.34 mg, 0.011 mmol) in dioxane (2.5 mL) and aqueous saturated NaHCO3 (0.5 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.22 (m, 3 H), 3.24-3.36 (m, 2 H), 3.39-3.75 (m, 3 H), 3.88-4.06 (m, 2 H), 4.06-4.16 (m, 1 H), 4.62-4.77 (m, 2 H), 7.05-7.21 (m, 2 H), 7.45-7.53 (m, 1 H), 7.55-7.62 (m, 1 H), 7.62-7.72 (m, 3 H), 7.90-7.97 (m, 2 H), 11.85-12.09 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C25H24FN5O3S, 494.16; found 494.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-489aa83653fe43999de189ee3e2ccb17
Source note	uspto-grants-2015_06