Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 16414272 | — |
| Reactant | 2-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole | HCID 66221540 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66717014 | HCID 66717014 | — |
Reaction Steps
A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (169 mg, 0.512 mmol, 1 eq), 2-picoline-5-boronic acid pinacol ester (137 mg, 0.614 mmol, 1.2 eq), PdCl2(PPh3)2 (73 mg, 0.102 mmol, 0.2 eq) and 2M aq Na2CO3 (1.5 mL) in dioxane (7 mL) was heated at 110° C. for 2 h. The solvent was removed under reduced pressure, redissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4 and concentrated. The residue (226. mg) was used in the next step of the synthesis without further purification. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mUrnin, 50° C.): tR=3.79 min, [M+H]+ m/z 342.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08815918B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-9aca8dac3b5c46e499edac28c0054835 |
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| Source note | uspto-grants-2014_08 |
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