HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1177457Generated: October 26, 2026
Cesium carbonate → 3-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile
https://huagongshe.com/reaction/1177457
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-3-methylbenzonitrile | HCID 2737494 | — |
| Reactant | 5-(1-Phenylcyclopropyl)thiazolo[5,4-b]pyridine | HCID 59174874 | — |
| Catalyst | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-Methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile | HCID 67111682 | — |
Reaction Steps
A mixture of 5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (48.3 mg, 191 μmol), 4-bromo-3-methylbenzonitrile (45.0 mg, 230 μmol), PdCl2(AmPhos)2 (6.78 mg, 9.57 μmol), and cesium carbonate (187 mg, 574 μmol) in DMF (1.6 mL) was heated (microwave) under argon at 190° C. for 40 min. The reaction mixture was then partitioned between EtOAc (40 mL) and water (15 mL). The organic layer was separated, washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0-100% EtOAc/hexanes) furnished 3-methyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzonitrile as a light-yellow solid. MS (ESI) m/z: Calculated: 367.1; Observed: 368.1 (M++1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07842685B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-f186310df2a94c9bb646003c4693f727 |
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| Source note | uspto-grants-2010_11 |
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