HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → tert-Butyl 2-(4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(2-methoxyethyl)carbamate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | tert-Butyl 2-methoxyethyl(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)carbamate | HCID 57919493 | — |
| Reactant | 7-(2-Fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine | HCID 59457661 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | tert-Butyl 2-(4-(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1H-pyrazol-1-yl)ethyl(2-methoxyethyl)carbamate | HCID 57919561 | — |
Reaction Steps
A mixture of 78 (369.3 mg, 0.93 mmol), 7-(2-fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine (24) [US 2006/0287343 A1](466.6 mg, 1.12 mmol), Pd(PPh3)4 (54 mg, 0.05 mmol) and Na2CO3 (305 mg, 2.8 mmol) in DME (1.9 mL) was heated to reflux overnight under nitrogen. It was then diluted with DCM, washed with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue was purified by flash chromatography, eluents EOAc/Hex 1:1, EtOAc, 5% MeOH in DCM affording title compound 79 (203 mg, 39%) as brown syrup. MS (m/z): 558.2 (100%) (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08846927B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-192e17c00a464e8598b0cb90638d773e |
| Source note | uspto-grants-2014_09 |