Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Aminobenzonitrile | HCID 13396 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | (1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine | HCID 57799674 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 57799866 | HCID 57799866 | — |
Reaction Steps
(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg), 4-amino-benzonitrile (85 mg), Cs2CO3 (376 mg), 2,2′-Bis(diphenylphosphino)-1′1-binaphthyl (BINAP) (44 mg), Pd(OAc)2 (8 mg), 1,4-dioxane (2 ml), N-methyl-pyrrolidone (NMP) (0.2 ml), were placed in a microwave bottle. The mixture was heated at 150° C. for 30 minutes under microwave irradiation and purified by preparative LC-MS to give 4-[6-methoxy-3-(5-methyl-1H-pyrazol-3-ylamino)-isoquinolin-1-ylamino]-benzonitrile. LC-MS m/e 371 (MH+). 1H NMR(DMSO): δ 2.26(s, 3H), δ 3.86(s, 3H), δ 5.75(s, 1H), δ 6.52(m, 1H), δ 6.79(d, 1H), δ 7.12(s, 1H), δ 7.65(d, 2H), δ 8.20(m, 3H), δ 8.65(s,1H), δ 9.30(s, 1H), δ 11.75(s,1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07572809B2 |
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| Source dataset | uspto-grants-2009_08 |
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| ORD ID | ord-0ed15bd9328b4c12b559f75601ac8e96 |
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| Source note | uspto-grants-2009_08 |
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