Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethyl Ether | HCID 3283 | — |
| Reactant | 5-Bromo-2,3-dichloropyridine | HCID 12747760 | — |
| Reactant | HCID 178451183 | HCID 178451183 | — |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | HCID 6505921 | — |
| Catalyst | Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzene | HCID 129828017 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 58447890 | HCID 58447890 | — |
Reaction Steps
To a sealed tube were added 5-bromo-2,3-dichloropyridine 184-1 (113 mg, 0.50 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride 86-5 in ether (1.2 mL, 0.60 mmol), Pd(dba)2 (14 mg, 0.025 mmol), Q-phos (36 mg, 0.05 mmol) and THF (1.5 mL). The reaction mixture was bubbled with nitrogen for 1 minute and stirred at 70° C. overnight. After cooling to room temperature, all the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography and eluted with 20% ethyl acetate in hexane to give tert-butyl 2-(5,6-dichloropyridin-3-yl)acetate 184-3. MS m/z 262.1 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08546396B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-2641e5e6c10745a585a72e13b3f1361d |
|---|
| Source note | uspto-grants-2013_10 |
|---|
