Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Bromoisoquinoline | HCID 736487 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 82582561 | HCID 82582561 | 99.3% |
Reaction Steps
A mixture of 5-bromoisoquinoline (4.07 g, 19.6 mmol), morpholine (3.41 mL, 39.1 mmol), Cs2CO3 (12.75 g, 39.1 mmol), Pd(OAc)2 (220 mg, 0.98 mmol) and BINAP (609 mg, 0.98 mmol) in toluene (160 mL) was heated at 110° C. for 6 h under N2. The mixture was then concentrated in vacuo and the black residue obtained was taken up in DCM and filtered over Celite. The filtrate was concentrated in vacuo and the brown oil obtained was purified by flash chromatography (SiO2, cHex to AcOEt) to give the title compound (4.17 g) as a brown oil. UPLC-MS: MS 215.1 (M+H+); UPLC rt 0.57 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853203B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-e8044fbe8ec6475a92a1dda7ec97041f |
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| Source note | uspto-grants-2014_10 |
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