5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 60198095, compound

Participants

Role	Name	HCID	Charge
Reactant	5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine	HCID 24208789	—
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	HCID 60198095	HCID 60198095	—

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), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (61.8 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 3.14-3.26 (m, 2 H), 3.31-3.45 (m, 6 H), 3.54-3.65 (m, 2 H), 3.93-4.03 (m, 1 H), 4.03-4.13 (m, 1 H), 4.62-4.72 (m, 2 H), 6.51-6.61 (m, 1 H), 7.44-7.53 (m, 1 H), 7.53-7.60 (m, 1 H), 7.60-7.68 (m, 2 H), 7.89-7.96 (m, 2 H), 8.67-8.73 (m, 1 H), 8.99-9.07 (m, 1 H), 11.76-12.07 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-947b371b2a1b43e7bf12f82bdc295576
Source note	uspto-grants-2015_06