Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,3-Dichloroisoquinoline | HCID 298625 | — |
| Reactant | (1,1'-Binaphthalen)-2-yldi-tert-butylphosphine | HCID 2734941 | — |
| Reactant | HCID 7009454 | HCID 7009454 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 59756932 | HCID 59756932 | — |
Reaction Steps
A toluene (3 mL) solution containing 1,3-dichloroisoquinoline (50 mg, 0.25 mmol), 4-(hydroxymethyl)benzoate (105 mg, 0.63 mmol), cesium carbonate (206 mg, 0.63 mmol), palladium acetate (5 mg, 0.02 mmol) and racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (14 mg, 0.035 mmol) was heated at 75° C. for 1.5 hours. The solution was partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4. The solution was filtered, concentrated and the residue purified by silica gel chromatography using hexanes/ethyl acetate gradient. 1H NMR (500 MHz, CDCl3): δ 8.30 (d, J=8.3 Hz, 1H); 8.13 (d, J=8.3 Hz, 2H); 7.72-7.70 (m, 2H); 7.65 (d, J=8.2 Hz, 2H); 7.59-7.55 (m, 1H); 7.34 (s, 1H); 5.68 (s, 2H); 3.98 (s, 3H). LCMS2 2.73 min. (M+H)=328
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08318760B2 |
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| Source dataset | uspto-grants-2012_11 |
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| ORD ID | ord-b057d5aad7ce454c86d78b68931e1a80 |
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| Source note | uspto-grants-2012_11 |
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