Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Reactant | 2-(2-Methyl-5-phenylpyridine-3-carbonyl)benzaldehyde | HCID 57722810 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57722772 | HCID 57722772 | — |
Reaction Steps
A flask was charged with 2-[(2-methyl-5-phenylpyridin-3-yl)carbonyl]benzaldehyde (6.2 mg, 0.02 mmol) and MeOH (1 mL). LiHMDS (25 μl, 1.0 M in THF) was added and the vessel was heated in the Biotage Initiator series microwave for 30 min. at 100° C. The mixture was then diluted with EtOAc, washed with water and brine, then dried over Na2SO4. The solution was concentrated in vacuo and purified by reverse phase HPLC (0-100% CH3CN/water with a 0.1% TFA modifier) to afford the title compound. 1H NMR (600 MHz, CD3OD) δ 9.15 (d, 1H), 8.76 (d, 1H), 8.25 (d, 1H), 7.77 (m, 4H), 7.66 (t, 1H), 7.54 (t, 2H), 7.45 (m, 2H0, 7.36 (d, 1H). LRMS (APCI) calculated for C20H14NO [M+H]+, 284.1; found 283.8
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07550478B2 |
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| Source dataset | uspto-grants-2009_06 |
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| ORD ID | ord-80f273e5929d465dafb9bc3ee2db5d85 |
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| Source note | uspto-grants-2009_06 |
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