Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Prop-1-en-2-yl)boronic acid | HCID 10855372 | — |
| Reactant | HCID 59559933 | HCID 59559933 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 59560104 | HCID 59560104 | 43% |
Reaction Steps
A solution of 2-bromo-6-isopropoxy-N-(5-methylpyridin-2-yl)benzofuran-4-carboxamide (263 mg, 0.68 mmol), isopropenyl boronic acid (58.4 mg, 0.68 mmol), Pd(PPh3)2Cl2 (23.9 mg, 0.034 mmol) and aqueous Na2CO3 (1.0 M in H2O, 1.36 mL) in 1.4 mL of CH3CN was heated in a microwave reactor at 150° C. for 5 min. The solvent was removed in vacuo. The residue was purified with Biotage column chromatography to give a light yellow solid (102 mg, 43% yield). 1H NMR (400 MHz, CDCl3) δ 9.07 (s, 1 H) 8.30 (d, J=8.56 Hz, 1 H) 7.96 (d, J=2.01 Hz, 1 H) 7.56 (dd, J=8.56, 2.27 Hz, 1 H) 7.26 (d, J=2.27 Hz, 1 H) 7.14 (d, J=1.51 Hz, 1 H) 7.09 (s, 1 H) 5.76 (s, 1 H) 5.17 (s, 1 H) 4.53-4.59 (m, 1 H) 2.27 (s, 3H) 2.11 (s, 3 H) 1.36 (d, J=6.04 Hz, 6 H); LCMS for C21H22N2O3 m/z 351.10 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07842713B2 |
|---|
| Source dataset | uspto-grants-2010_11 |
|---|
| ORD ID | ord-2340a91fe9c04af98d412e37740e060d |
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| Source note | uspto-grants-2010_11 |
|---|
