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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2222584Generated: October 31, 2026

Dimethylformamide → HCID 69311233, compound

https://huagongshe.com/reaction/2222584

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant1-HydroxybenzotriazoleHCID 75771—
ReactantDiisopropylethylamineHCID 81531—
Reactant1H-Indazol-5-amineHCID 88012—
SolventAcetic AcidHCID 176—
ProductHCID 69311233HCID 6931123395%

Reaction Steps

Into a solution of 5-aminoazaindole (0.6 g, 4.5 mmol) in dry DMF (11 mL) N-[(1H-1,2,3-benzotriazol-1-yloxy)(dimethylamino)methylene]-N-methylmethanaminium tetrafluoroborate (TBTU, 1.45 g, 9 mmol), 1-hydroxybenzotriazole (HOBt, 0.69 g, 9 mmol) and glacial AcOH (260 micro), diisopropylethylamine (DIPEA, 3.12 mL, 18 mmol) was slowly dropped in ca. 30′ under stirring. The reaction mixture was stirred at room temperature for 18 h, concentrated and the residue was purified by flash chromatography eluting with dichloromethane/MeOH 10:1. The desired 1H-pyrrolo[2,3-b]pyridin-5-ylacetamide (title compound) was obtained in 95% yield (0.78 g, 4.2 mmol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07371862B2
Source datasetuspto-grants-2008_05
ORD IDord-96ec231f5a0d46fbb706c2b18e5e006e
Source noteuspto-grants-2008_05