Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dipropylamine | HCID 8902 | — |
| Reactant | 6-Bromopyridine-2-carbaldehyde | HCID 2757009 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | 1,2-Dichloroethane | HCID 11 | — |
| Product | HCID 86613887 | HCID 86613887 | 73% |
Reaction Steps
Dipropylamine (7.4 mL, 54 mmol) and 6-bromopyridine-2-carbaldehyde (5.0 g, 27 mmol) were dissolved in 1,2-dichloroethane (50 mL). 2 drops of glacial acetic acid was added followed by sodium triacetoxyborohydride (11.4 g, 54 mmol). The reaction was stirred at 50° C. for 1 h. The reaction was cooled and quenched with water. The solution was diluted with saturated sodium bicarbonate and extracted with ethyl acetate (3 times). The organic layers were dried over magnesium sulfate, filtered and concentrated. Flash chromatography gave 5.34 g (73% yield) of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07897607B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-69cd6ed1cc584df3a98171dd07898104 |
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| Source note | uspto-grants-2011_03 |
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