HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 66690597, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine | HCID 59557920 | — |
| Reactant | 2-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole | HCID 66221540 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 66690597 | HCID 66690597 | 66.3% |
Reaction Steps
Dioxane (5 mL) and 2M aq Na2CO3 (1.5 mL) were added to 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (200 mg) and (5-amino-6-methoxypyridin-3-yl)boronic acid pinacol ester (200 mg), and the suspension was degassed under vacuum and filled with argon (3×). PdCl2(PPh3)2 (90 mg) was quickly added, and the reaction mixture was stirred at reflux for 2 h. Water was added, and a precipitate formed that was filtered off and washed with water followed by ether and ether/MeOH 10:1 and dried to give the desired product (150 mg) that was used without further purification in the subsequent step. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.12 min, [M+H]+ m/z 373.9.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08815918B2 |
| Source dataset | uspto-grants-2014_08 |
| ORD ID | ord-d5f8c5308a704338832ad2f29ca7d967 |
| Source note | uspto-grants-2014_08 |