Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | (4-Cyano-3-fluorophenyl)boronic acid | HCID 2783130 | — |
| Reactant | 1-(3-Bromopyridin-4-yl)ethanol | HCID 66797853 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71104923 | HCID 71104923 | 52.3% |
Reaction Steps
To the solution of 4-cyano-3-fluoro phenylboronic acid (247 mg, 1.50 mmol), 1-(3-Bromo-pyridin-4-yl)-ethanol (303 mg, 1.50 mmol) and PdCl2(dppf). CH2Cl2 adduct (98 mg, 0.12 mmol) in DMF (6 mL) was added 2M Na2CO3aq (1.50 ml, 3.00 mmol) under Nitrogen atmosphere. The mixture was stirred and heated at 100° C. for 4 hrs. After letting cool to room temperature, solvent was removed in vacuo. The resulting residue was dissolved in DCM and saturated NH4Cl solution. After extraction with DCM and separation, the combined extracts were concentrated and purified by ISCO 12 g (10% MeOH/DCM=0-25%) to give 2-Fluoro-4-[4-(1-hydroxy-ethyl)-pyridin-3-yl]-benzonitrile (190 mg, 52%) as colorless solid; ESI-MS m/z: 243 [M+1]+, Retention time 1.05 min
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08519134B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-ec31edd613dd426cac6a14377ece56ed |
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| Source note | uspto-grants-2013_08 |
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