HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methanol → 6-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | tert-Butyl methyl ether | HCID 15413 | — |
| Reactant | 6-Bromo-pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester | HCID 59316820 | — |
| Reactant | HCID 178477796 | HCID 178477796 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 6-methyl-pyrrolo[2,1-b]thiazole-7-carboxylic Acid Ethyl Ester | HCID 59316837 | — |
Reaction Steps
Under nitrogen atmosphere a solution of dimethylzinc in toluene (1.2 M, 19.1 mL) is added to a mixture of 6-bromo-pyrrolo[2,1-b]thiazole-7-carboxylic acid ethyl ester (11.4 mmol) and [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.23 mmol, complex with CH2Cl2) in dioxane (35 mL). The mixture is heated to reflux for 2 h, stirred at RT for 12 h and diluted by addition of MeOH (2.3 mL) and TBME. The mixture is washed with hydrochloric acid (1.0 M) and water, dried over MgSO4, concentrated in vacuo and purified by flash chromatography (gradient: heptane to heptane/EtOAc 8/2) to give the desired product. LC-MS: tR=0.91 min; [M+H]+=210.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08288435B2 |
| Source dataset | uspto-grants-2012_10 |
| ORD ID | ord-f038649624e5430c83e6b71d7fa5dc83 |
| Source note | uspto-grants-2012_10 |