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

Participants

Role	Name	HCID	Charge
Reactant	4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-1H-indole	HCID 59151337	—
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	5-(4-(methylsulfonyl)benzyl)-2-(2-(trifluoromethyl)-1H-indol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197657	—

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, 63.5 mg, 0.161 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-1H-indole (100 mg, 0.321 mmol) and PdCl2(dppf) (5.88 mg, 8.04 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.21 (m, 3 H), 3.23-3.34 (m, 3 H), 3.56-3.66 (m, 2 H), 3.88-4.03 (m, 2 H), 4.05-4.16 (m, 1 H), 4.59-4.68 (m, 1 H), 4.71 (s, 2 H), 7.41-7.48 (m, 1 H), 7.56 (s, 2 H), 7.65 (d, J=8.34 Hz, 3 H), 7.79-7.86 (m, 1 H), 7.94 (d, J=8.34 Hz, 2 H), 12.56-12.65 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C26H24F3N5O3S, 544.16; found 544.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-6dea955ad7ab49afabedefecc2cb5c8b
Source note	uspto-grants-2015_06