Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | HCID 118021566 | HCID 118021566 | — |
| Reactant | 2-[2-(Cyclopropylmethoxy)-5-(methylsulfonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | HCID 123434859 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Solvent | Dichloromethane methanol | HCID 21226129 | — |
| Product | HCID 118021752 | HCID 118021752 | 48.4% |
Reaction Steps
To a solution of the title compound of step 7 (60 mg, 0.26 mmol), the title compound of Example 90, step 1 (111.2 mg, 0.32 mmol) and K2CO3 (107 mg, 0.78 mmol) in dioxane (4 mL) and water (1 mL) was added Pd(dppf)Cl2 (6 mg) under N2. The mixture was heated at 85° C. overnight. EA extractive work up followed by prep-TLC (DCM/MeOH=25:1) gave the title compound (47 mg, 48%) as a yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ 7.83 (dd, J=8.7, 2.7 Hz, 1H), 7.66 (d, J=2.9 Hz, 1H), 7.58 (s, 1H), 7.25 (d, J=8.7 Hz, 1H), 3.95 (d, J=6.9 Hz, 2H), 3.46 (s, 3H), 3.17 (s, 3H), 2.65-2.70 (m, 4H), 1.91-1.97 (m, 2H), 1.13-1.18 (m, 1H), 0.50-0.54 (m, 2H), 0.26-0.30 (m, 2H). LCMS: 374 (M+1)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09034900B2 |
|---|
| Source dataset | uspto-grants-2015_05 |
|---|
| ORD ID | ord-07141ac9ebda470bb713baa159d17ffb |
|---|
| Source note | uspto-grants-2015_05 |
|---|
