(1-Acetyl-1H-pyrrolo[2,3-c]pyridin-4-yl)boronic acid → 5-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[2,3-c]pyridin-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Participants

Role	Name	HCID	Charge
Reactant	(1-Acetyl-1H-pyrrolo[2,3-c]pyridin-4-yl)boronic acid	HCID 68195100	—
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-(1H-pyrrolo[2,3-c]pyridin-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine	HCID 60197987	—

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-acetyl-1H-pyrrolo[2,3-c]pyridin-4-ylboronic acid (77 mg, 0.380 mmol) and PdCl2(dppf) (6.95 mg, 9.50 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.08-3.19 (m, 1 H), 3.21 (m, 2 H), 3.23-3.34 (m, 2 H), 3.47-3.56 (m, 1 H), 3.57-3.67 (m, 1 H), 3.70-3.81 (m, 1 H), 3.93-4.01 (m, 2 H), 4.06-4.15 (m, 1 H), 4.49-4.58 (m, 1 H), 4.64-4.80 (m, 2 H), 7.55-7.68 (m, 3 H), 7.69-7.75 (m, 1 H), 7.88-7.98 (m, 2 H), 8.28-8.37 (m, 1 H), 8.86-8.96 (m, 1 H), 9.05-9.15 (m, 1 H), 12.85-12.97 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.5.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09045496B2
Source dataset	uspto-grants-2015_06
ORD ID	ord-5269046704f24898a723746cfb6eaeb8
Source note	uspto-grants-2015_06