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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2203770Generated: November 1, 2026

Lithium Hydroxide → N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

https://huagongshe.com/reaction/2203770

Reaction equation

Participants

RoleNameHCIDCharge
ReactantLithium HydroxideHCID 3939—
ReactantBis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 152842—
ReactantN(1)-methyl-2-pyridone-5-carboxylic acidHCID 592704—
Reactant5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amineHCID 60205276—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
ProductN-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamideHCID 6020534369.3%

Reaction Steps

TEA (0.61 mL, 4.35 mmol) was added to 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-amine (0.20 g, 0.87 mmol, Example 1, Step H), 1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid (0.17 g, 1.13 mmol) and BOP-Cl (0.33 g, 1.30 mmol) in DCM (10 mL). The reaction was stirred at room temperature for 1 hour, and then a LiOH solution (3 mL, 2N) was added. The mixture was stirred for 30 minutes, and water (10 mL) was added. The solid formed was collected by filtration, washed with DCM (10 mL) and dried to give N-(5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide (0.22 g, 69% yield) as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365568B2
Source datasetuspto-grants-2016_06
ORD IDord-e2acd038b99048f598cbbe2656ff2c12
Source noteuspto-grants-2016_06