Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | HCID 22563214 | HCID 22563214 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22563227 | HCID 22563227 | 76.8% |
Reaction Steps
To a 0° C. mixture of ethyl 2-formyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 6, 0.628 g, 2.5 mmol) and acetic acid (0.71 mL, 12.5 mmol) in 1,2-dichloroethane (23 mL) was added sodium triacetoxyborohydride (1.06 g, 5.0 mmol). The mixture was stirred at 0° C. for 5 minutes and at room temperature for 24 hrs. A saturated solution of sodium bicarbonate (25 mL) and methylene chloride (25 mL) were added. After stirring vigorously for 5 minutes, the mixture was filtered. The collected solid was washed with water and methylene chloride, then dried in vacuo, leaving the title compound as a pale yellow solid (0.486 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06861438B2 |
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| Source dataset | uspto-grants-2005_03 |
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| ORD ID | ord-cef5cf4fc3d2498db4f4249f85bc922f |
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| Source note | uspto-grants-2005_03 |
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