Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Pyrrole | HCID 8027 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide | HCID 68775075 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58789394 | HCID 58789394 | — |
Reaction Steps
To a solution of 2-(4-bromophenyl)-N-isobutyl-2-methylpropanamide (example 1a) (100 mg, 0.33 mmol) in DMF (5 mL) was added 1-H-pyrrole (0.66 mmol, 44 mg), K2CO3 (2.4 eq., 115 mg) and catalytic CuI (3 mg). The reaction tube was sealed, and heated in a microwave at 195° C. for 3 hours. The solution was extracted with ethyl acetate and washed with cold water. The product was purified twice by reverse phase HPLC (10 to 95% acetonitrile/water). The compound was re-dissolved in ethanol and evaporated to dryness. 1H NMR (400 MHz, DMSO-d6): δ 0.75 (d, 6H)), 1.48 (s, 6H), 1.70 (m, 1H), 2.85 (t, 2H), 6.1 (d, 2H), 7.3 (m, 5H), 7.5 (d,2H). MS: M+H=285.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07842324B2 |
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| Source dataset | uspto-grants-2010_11 |
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| ORD ID | ord-28489442bc3844b28f283e6997064a7c |
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| Source note | uspto-grants-2010_11 |
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