Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Citric Acid | HCID 311 | — |
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide | HCID 67974626 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| 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 | — |
| Product | HCID 67974867 | HCID 67974867 | 5.2% |
Reaction Steps
A mixture of N-(7-bromoisoquinolin-3-yl)cyclopropanecarboxamide (70.6 mg, 0.242 mmol), sodium tert-butoxide (36.0 mg, 0.374 mmol), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (13.0 mg, 0.0126 mmol), and Q-Phos (19.3 mg, 0.0272 mmol) in toluene (1.0 mL, 9.4 mmol) was subjected to microwave irradiation at 120° C. for 30 minutes. The reaction mixture was neutralized with 10% aqueous citric acid and extracted with dichloromethane. The organic extract was dried over MgSO4, filtered, and evaporated in vacuo. The crude product was purified via reverse phase HPLC and lyophilized to yield 3.6 mg (5.2%) of N-(7-tert-butoxyisoquinolin-3-yl)cyclopropanecarboxamide. LCMS (ESI): RT (min)=4.371, M+H=285.1, method=E; 1H NMR (400 MHz, DMSO-d6) δ 10.78 (s, 1H), 9.06 (s, 1H), 8.40 (s, 1H), 7.78 (d, J=8.9 Hz, 1H), 7.60 (d, J=2.2 Hz, 1H), 7.35 (dd, J=8.9, 2.4 Hz, 1H), 2.12-1.97 (m, 1H), 1.39 (s, 9H), 0.91-0.75 (m, 4H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09206175B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-c04fa385b24c4c7ca10b3968ca6f0754 |
|---|
| Source note | uspto-grants-2015_12 |
|---|
