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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1432327Generated: October 26, 2026

Tri-o-tolylphosphine → 1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(phenylsulfonyl)-5-(2-thienyl)-

https://huagongshe.com/reaction/1432327

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTri-o-tolylphosphineHCID 80271—
Reactant2-(Tri-n-butylstannyl)thiopheneHCID 2779373—
Reactant5-Bromo-1-(phenylsulfonyl)-1h-pyrrolo[2,3-b]pyridine-3-carbonitrileHCID 68952447—
CatalystBis(acetonitrile)dichloropalladiumHCID 6093782—
SolventTolueneHCID 1140—
Product1H-Pyrrolo[2,3-b]pyridine-3-carbonitrile, 1-(phenylsulfonyl)-5-(2-thienyl)-HCID 6895678139.1%

Reaction Conditions

Temperature90 °C

Reaction Steps

A mixture of 8 (50.0 mg, 0.128 mmol), 2-(tributylstannyl)thiophene (88 μL, 0.276 mmol), dichlorobis(acetonitrile)palladium (II) (4.0 mg, 0.0138 mmol), tri-o-tolylphosphine (8.0 mg, 0.0276 mmol) and toluene (1.0 mL) were heated at 90° C. overnight. The mixture was separated by PTLC using ethyl acetate:hexane (3:7) as eluent to give 11 as a white solid (18.3 mg, 36%); 1H NMR (400 MHz, CDCl3) δ 8.80 (d, J=2.1 Hz, 1H), 8.28 (m, 3H), 8.16 (d, J=2.1 Hz, 1H), 7.68 (tt, J=7.5, 1.2 Hz, 1H), 7.57 (t, J=4.1 Hz, 2H), 7.37 (m, 2H), 7.13 (dd, J=5.1, 3.6 Hz, 1H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07612086B2
Source datasetuspto-grants-2009_11
ORD IDord-8bad412eb06445f5af18eb27604c9149
Source noteuspto-grants-2009_11