Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 5-hydroxybenzofuran-2-carboxylate | HCID 12208973 | — |
| Reactant | 2-Chloro-(1,3)thiazolo(4,5-b)pyridine | HCID 51358428 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 68769046 | HCID 68769046 | 102.1% |
Reaction Steps
To a solution of 5-hydroxy-benzofuran-2-carboxylic acid methyl ester (1.5 g, 7.8 mmol) in DMF (78 mL) was added Cs2CO3 (7.6 g, 26 mmol) and 2-chloro-thiazolo[4,5-b]pyridine (1.6 g, 7.8 mmol). The reaction mixture was heated (50° C., 10 h), cooled (rt) and water was added (50 mL). The resulting solid was filtered to provide the title compound as a colorless solid (2.6 g, 100%). MS (ESI): mass calcd. for C16H10N2O4S, 326.0; m/z found, 327.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.03 (dd, J=7.9, 1.6, 1H), 7.84 (d, J=2.4, 1H), 7.64 (d, J=9.0, 1H), 7.54 (d, J=0.9, 1H), 7.47 (dd, J=9.0, 2.5, 1H), 7.22 (dd, J=7.9, 4.8, 1H), 4.04-3.86 (m, 3H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399465B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-fdcac38d8e504bcb879abe32535d6d64 |
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| Source note | uspto-grants-2013_03 |
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