Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanolamine | HCID 700 | — |
| Reactant | 1,10-Phenanthroline | HCID 1318 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide | HCID 67974626 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | HCID 67976356 | HCID 67976356 | 17% |
Reaction Steps
N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (150 mg, 0.51 mmol), copper(I) iodide (96 mg, 0.51 mmol), 1,10-phenanthroline (100 mg, 0.51 mmol) and cesium carbonate (216 mg, 0.66 mmol) were combined in a stainless steel container with 2-aminoethanol (3.0 mL). The resulting mixture was stirred at 120-140° C. for 12 hours under nitrogen. The reaction mixture was concentrated and purified via TLC to afford the desired product (23.4 mg, 17%). LCMS (ESI): RT (min)=0.959, M+H+=271.8, method=A; 1H NMR (400 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.75 (s, 1H), 8.19 (s, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 6.77 (s, 1H), 6.00 (s, 1H), 4.74 (s, 1H), 3.61 (d, J=5.6 Hz, 2H), 3.17 (d, J=4.8 Hz, 2H), 1.99-1.95 (m, 1H), 0.79-0.75 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08623889B2 |
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| Source dataset | uspto-grants-2014_01 |
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| ORD ID | ord-77000a0aadb844caabe9550c2d290bd6 |
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| Source note | uspto-grants-2014_01 |
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