Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzo[b]furan-2-boronic acid | HCID 2776266 | — |
| Reactant | HCID 59424803 | HCID 59424803 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Product | HCID 59424800 | HCID 59424800 | — |
Reaction Steps
To a degassed solution of (5-bromo-3-fluoro-pyridin-2-yl)-methyl-carbamic acid tert-butyl ester (310 mg, 1.01 mmol) in EtOH (10 mL) were added Pd(PPh3)2Cl2 (142 mg, 0.20 mmol), bezofuran boronic acid (291 mg, 1.52 mmol) and Et3N (283 μL, 2.03 mmol). The reaction was stirred in a microwave reactor for 30 minutes at 100° C. The volatiles were removed under reduced pressure and the residue was purified by flash column chromatography using 10% EtOAc in hexane to obtain title compound (130 mg) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.68 (br. s, 1 H) 7.80 (d, J=11.71 Hz, 1 H) 7.42 (d, J=8.98 Hz, 1 H) 7.04 (s, 2 H) 6.93 (dd, J=8.98, 2.34 Hz, 1 H) 3.85 (s, 3H) 3.35 (s, 3 H) 1.46 (s, 9 H). ESMS: m/z 359.41 (M+1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07772256B2 |
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| Source dataset | uspto-grants-2010_08 |
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| ORD ID | ord-c2f676beba9147ecb725ed8ce504e8e1 |
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| Source note | uspto-grants-2010_08 |
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