HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1191085Generated: October 31, 2026
Dimethylformamide → 5-(2-Cyclopropylmethylamino-thiazol-4-yl)-pyridine-2-carbonitrile
https://huagongshe.com/reaction/1191085
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 59822270 | HCID 59822270 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 5-(2-Cyclopropylmethylamino-thiazol-4-yl)-pyridine-2-carbonitrile | HCID 59828899 | 38% |
Reaction Steps
Slurry 6-bromo-3-(2-cyclopropylmethylamino-thiazol-4-yl)-pyridine (1.1 g, 3.6 mmol), 1,1′-bis-(diphenylphosphino)ferrocene (320 mg, 0.6 mmol), zinc cyanide (337 mg, 2.9 mmol) and tris(dibenzylideneacetone)dipalladium(0) (231 mg, 0.25 mmol) in wet DMF (6 mL). Stir the mixture in a sealed tube at 115° C. for 6 h. Cool the mixture to room temperature, dilute with EtOAc (50 mL) and wash with 5% aqueous sodium chloride (3×30 mL). Collect the organic layer and concentrate in vacuo. Purify the residue by chromatography on silica gel (40 g) eluting with hexane/(THF with 1% methanol) (4:1) to obtain the desired intermediate (350 mg, 38%). MS (ES+) m/z: 257.3 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680091B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-d31dcfd8b2e440fb89eaabd5ea49520c |
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| Source note | uspto-grants-2014_03 |
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