Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 2-Chloromethyl 2-(trimethylsilyl)ethyl ether | HCID 2724271 | — |
| Reactant | 4-Chloro-5-fluoro-3-iodo-1H-pyrrolo[2,3-b]pyridine | HCID 49761627 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 90413560 | HCID 90413560 | — |
Reaction Steps
A solution of Example 263A (2.8 g, 9.44 mmol) in tetrahydrofuran (200 mL) was cooled to 0° C. and sodium hydride (0.34 g, 14.17 mmol) was added. The mixture was stirred at 0° C. for 30 minutes and (2-(chloromethoxy)ethyl)trimethylsilane (2.5 mL, 14.17 mmol) was added. The mixture was warmed to room temperature, stirred for 2 hours, quenched with brine and extracted with ethyl acetate (twice). The organic phase was concentrated and purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. MS (ESI+) m/z 427 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09073922B2 |
|---|
| Source dataset | uspto-grants-2015_07 |
|---|
| ORD ID | ord-085c445966b64965a11a1f0267fd5b05 |
|---|
| Source note | uspto-grants-2015_07 |
|---|
