Triethylamine → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-fluoro-4-methoxybenzamide

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	Bis(2-oxo-3-oxazolidinyl)phosphinic chloride	HCID 152842	—
Reactant	3-Fluoro-4-methoxybenzoic acid	HCID 2733401	—
Reactant	5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine	HCID 60205276	—
Solvent	Dichloromethane	HCID 6344	—
Product	N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-fluoro-4-methoxybenzamide	HCID 60205472	90.2%

Reaction Steps

A mixture of 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (200 mg, 0.87 mmol, Example 1, Step H), 3-fluoro-4-methoxybenzoic acid (311 mg, 1.83 mmol), BOP-Cl (0.465 g, 1.83 mmol), and triethylamine (0.606 mL, 4.35 mmol) in DCM (5 mL) was processed as described in Example 62, Step A, to provide N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-fluoro-4-methoxybenzamide (300 mg, 90% yield) as a solid. LCMS (APCI+) m/z 381.9, 383.9 (M+H)+, Retention time=3.23 minutes (Method 2).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08981085B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-4d2d0c5449e148eb825b54f709627a2e
Source note	uspto-grants-2015_03