HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,3-Thiazol-2-ylmethanol → Ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,3-Thiazol-2-ylmethanol | HCID 2795213 | — |
| Reactant | Cyanomethylenetributylphosphorane | HCID 4622928 | — |
| Reactant | ethyl 5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate | HCID 60146028 | — |
| Product | Ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate | HCID 66845785 | 83.1% |
Reaction Steps
This compound was prepared according to a process similar to that described in step 5.1. by reacting 390 mg (1.51 mmol) of ethyl 5-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine-2-carboxylate (WO2008/107543) with 348 mg (3.02 mmol) of thiazol-2-ylmethanol in the presence of 0.92 g (3.826 mmol) of (cyanomethylene)-tributylphosphorane (CMBP). The reaction mixture is then purified by flash chromatography on a column of silica gel in a mixture of heptane and ethyl acetate to give 446 mg of the expected product in the form of an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08354425B2 |
| Source dataset | uspto-grants-2013_01 |
| ORD ID | ord-04bccdf9afdc474a9d9ff083ab0e6c6c |
| Source note | uspto-grants-2013_01 |