Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 4-Chloro-5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidine | HCID 118022445 | — |
| Reactant | 2-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinolin-1(2H)-one | HCID 123809499 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | US10023592, Example 311 | HCID 118021982 | 68.1% |
Reaction Steps
The title compound of step 4 (5.00 g, 19.08 mmol), the title compound of Example 89, step 1 (5.98 g, 20.99 mmol), K3PO4 (12.13 g, 57.24 mmol), and Pd(dppf)Cl2 (1.40 g, 1.91 mmol) in dioxane/H2O (50 mL/5 mL) were N2 purged and heated at 80° C. for 8 h. Silica gel chromatography (PE:EA=10/1˜1/1) to gave the title compound (5.01 g, yield: 68%) as a yellow solid. 1H NMR (CDCl3, 400 MHz) δ8.53 (s, 2H), 7.67-7.63 (m, 2H), 7.57-7.52 (m, 2H), 4.06 (d, J=6.8 Hz, 2H), 3.71 (s, 3H), 3.37 (s, 3H), 1.17 (m, 1H), 0.61 (m, 2H), 0.30 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09034900B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-41d7149d7d2541628c4f64a6616c4382 |
|---|
| Source note | uspto-grants-2015_05 |
|---|
