Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methanesulfonyl)phenylboronic acid | HCID 2734364 | — |
| Reactant | HCID 86674888 | HCID 86674888 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67973481 | HCID 67973481 | — |
Reaction Steps
To a mixture of 4-(5-chloro-furo[3,2-b]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (50 mg) and 4-(methanesulfonyl)phenyl boronic acid (45 mg) in [1,4]dioxane (1.5 mL) in a microwave oven suited vessel charged with a stir bar a 2 M aqueous Na2CO3 solution (1904) is added. The mixture is sparged with argon for 10 min and Pd(PPh3)4 (21 mg) is added. The vessel is capped and the mixture is stirred under microwave irradiation at 140° C. for 35 min. After cooling the mixture to room temperature, dichloromethane and water are added. The organic phase is washed with brine, dried (MgSO4) and the solvent is evaporated. The crude product is purified by HPLC on reversed phase (MeOH/H2O/TFA). Yield: 25 mg (37% of theory); LC (method 2): tR=1.36 min; Mass spectrum (ESI+): m/z=457 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08669271B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-e5bbde75b6d24790ab2604b205752bd0 |
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| Source note | uspto-grants-2014_03 |
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