Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 19007564 | HCID 19007564 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 22721628 | HCID 22721628 | 67% |
Reaction Steps
A suspension of 7-bromo-4-methoxy-benzo[b]thiophene-2-carboxylic acid methyl ester (5 g, 16.6 mmol) with bis(triphenylphosphine)palladium (II) chloride (350 mg, 0.496 mmol, 0.03 eq.) and K2CO3 (4.88 g, 49.8 mmol, 3 eq.) under argon in dioxane (40 ml) at 20° C. was stirred for 60 minutes. Phenylboronic acid (2.16 g, 17.4 mmol, 1.05 eq.) and 2N Na2CO3 (80 ml) was then added and the mixture heated to 100° C. overnight. After cooling, filtration and acidification to pH 1 with aq. HCl the product precipitated and was filtered off and dried under vacuum at 50° C. to afford the title compound (3.16 g, 67% yield) as a light brown solid. MS m/z=282.9 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06730670B2 |
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| Source dataset | uspto-grants-2004_05 |
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| ORD ID | ord-6241b40a182d4d24ba8982e30fc2da75 |
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| Source note | uspto-grants-2004_05 |
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