Sodium Carbonate → 2-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	5-Indolylboronic acid	HCID 2734361	—
Reactant	2-Bromo-7-iodo-5-tosyl-5H-pyrrolo[2,3-B]pyrazine	HCID 45789631	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Solvent	Acetonitrile	HCID 6342	—
Product	2-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine	HCID 86662678	—

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a stirred suspension of 2-bromo-7-iodo-5-tosyl-5H-pyrrolo[3,2-b]pyrazine [Intermediate AU] (0.25 g, 0.52 mmol) and 1H-indol-5-ylboronic acid (0.10 mg, 0.62 mmol) in CH3CN (20 mL) was added 1 M Na2CO3 (20 mL) followed by bis(triphenylphosphine)-palladium(II)dichloride (60 mg, 0.086 mmol). The resulting mixture was stirred for 2 h at 60° C. The title compound was isolated as a yellow solid via filtration from the CH3CN layer (0.23 g, 94%). HPLC retention time: 3.23 minutes. MS ESI (m/z): 467.2/469.2 (M+H)+, calc. 466.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08877772B2
Source dataset	uspto-grants-2014_11
ORD ID	ord-16de0752559c41fd92cd9de848fedc16
Source note	uspto-grants-2014_11