Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Iodine | HCID 807 | — |
| Reactant | 1-Bromo-1-propene | HCID 11533 | — |
| Reactant | HCID 58760742 | HCID 58760742 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Zinc bromide | HCID 10421208 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 91379151 | HCID 91379151 | — |
Reaction Steps
To Mg (143 mg, 5.8 mmol) in THF (4 mL) with trace of I2 was added α-bromopropene (583 μL) in order to maintain a 60° C. exotherm. After 30 minutes, a solution of ZnBr2 (1.31 g, 5.8 mmol) in THF (4 mL) was added. The reaction mixture was heated at 55° C. for 1 hour, cooled to r.t. and (Pd (dppf) CH2Cl2 (50 mg) was added followed by CuI (18.5 mg). After 5 minutes a solution of methyl (8-bromo-6-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetate (Example 22, Step 5, 200 mg, 0.59 mmol) in THF (7 mL) was added and the mixture was refluxed for 1 hour, cooled, quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to give the title compound (50 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07144913B2 |
|---|
| Source dataset | uspto-grants-2006_12 |
|---|
| ORD ID | ord-0854fb48adbd470db0cf99307948342c |
|---|
| Source note | uspto-grants-2006_12 |
|---|
