Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | HCID 46926618 | HCID 46926618 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 51003629 | HCID 51003629 | 41.8% |
Reaction Steps
Bromide intermediate (1-(3-(4-bromophenoxy)propyl)piperidin-4-yl)diphenylmethanol (A1) (75 mg, 0.15 mmol), Pd(dppf)Cl2 (15 mg), CsCO3 (150 mg), and pyridin-4-ylboronic acid (30 mg) was placed under an argon atmosphere in a microwave vial. Degassed THF (3 mL) and 0.1 mL of water was added via syringe and the mixture heated for 30 min. at 90° C. in a Biotage microwave reactor. The reaction was partitioned between EtOAc (10 mL) and water (3 mL) and the organic phase isolated. The organic phase was subsequently washed with brine, dried over Na2SO4, and concentrated to dryness. Purification by RP-HPLC afforded the title compound (30 mg, 41%): LC-MS (>98%) m/z=479.1 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09212180B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-67e90d5eb00744ca93c9cf7c9ba05f59 |
|---|
| Source note | uspto-grants-2015_12 |
|---|
