1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)ethanone → 2-(1H-indazol-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	1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)ethanone	HCID 68753107	—
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-indazol-4-yl)-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197984	—

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, 75 mg, 0.190 mmol), 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-1-yl)ethanone (109 mg, 0.381 mmol) and PdCl2(dppf) (6.97 mg, 9.52 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.18-3.38 (m, 5 H), 3.88-4.05 (m, 3 H), 4.09-4.19 (m, 2 H), 4.73 (m, 4 H), 7.49 (s, 1 H), 7.56 (s, 1 H), 7.65 (d, J=8.34 Hz, 2 H), 7.72 (s, 1 H), 7.84 (d, J=7.33 Hz, 1 H), 7.94 (d, J=8.34 Hz, 2 H), 8.61 (s, 1 H), 13.00-13.68 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-70654d836e464f2cbb04b3449d38eb80
Source note	uspto-grants-2015_06