Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Carboxyphenylboronic acid | HCID 2733957 | — |
| Reactant | N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamide | HCID 59165796 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Lumacaftor | HCID 16678941 | — |
Reaction Steps
N-(6-Chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (37 mg, 0.10 mmol) was dissolved in 1 mL of DMF in a reaction tube. 3-Boronobenzoic acid (25 mg, 0.15 mmol), 0.2 mL of an aqueous 2 M potassium carbonate solution, and Pd(dppf)Cl2 (8 mg) were added and the reaction mixture was heated for 10 min at 150° C. in the microwave. The reaction mixture was filtered and purified by reverse-phase preparative liquid chromatography to yield 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamido)-3-methylpyridin-2-yl)benzoic acid. ESI-MS m/z calc. 452.4. found 453.3 (M+1)+. Retention time 1.93 minutes.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08324207B2 |
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| Source dataset | uspto-grants-2012_12 |
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| ORD ID | ord-aef2c3dc61304faeaac6231ad1990835 |
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| Source note | uspto-grants-2012_12 |
|---|
