[4-Formyl-5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic acid tert-butyl ester synthesis

4synthesis methods

Product Name:[4-Formyl-5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic acid tert-butyl ester
CAS Number:552331-77-8
Molecular formula:C19H22N2O5
Molecular Weight:358.39

Carbamic acid, [5-[(4-methoxyphenyl)methoxy]-3-pyridinyl]-, 1,1-dimethylethyl ester (9CI)

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[4-Formyl-5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic acid tert-butyl ester

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Yield:552331-77-8 63%

Reaction Conditions:

Stage #1: [5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic acid tert-butyl esterwith n-butyllithium in tetrahydrofuran;hexane at -78 - -10; for 0.75 h;
Stage #2: Methyl formate in tetrahydrofuran;hexane at -78; for 0.166667 h;

Steps:

234.D [4-Formyl-5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic Acid Tert-Butyl Ester

Example 234D [4-Formyl-5-(4-methoxy-benzyloxy)-pyridin-3-yl]-carbamic Acid Tert-Butyl Ester To Example 234C (2.50 g, 7.54 mmol) in THF (125 mL) at -78° C. was added dropwise via syringe n-BuLi (6.64 mL of a 2.5 M solution in hexanes, 16.6 mmol). The resulting dark orange reaction mixture was slowly warmed to -10° C. over 45 min and then recooled to -78° C. Methyl formate (1.40 mL, 22.6 mmol) was added dropwise via syringe and the reaction was stirred an additional 10 min at -78° C. Saturated aqueous NH₄Cl was added and the quenched reaction mixture warmed to room temperature. H₂O and Et₂O were added and the layers separated. The organics were washed with brine and dried over MgSO₄. Flash chromatography (20-40-60-80% EtOAc/hexanes gave 0.3 g (12%) of recovered starting material, and 1.7 g (63%) of as a yellow solid. (¹H NMR (400 MHz, DMSO-D6) δ ppm 1.47 (s, 9H) 3.75 (s, 3H) 5.28 (s, 2H) 6.95 (d, J=8.59 Hz, 2H) 7.43 (d, J=8.59 Hz, 2H) 8.38 (s, 1H) 9.07 (s, 1H) 10.17 (s, 1H) 10.35 (s, 1H), ¹³C NMR (100 MHz, DMSO-D6) δ ppm 27.7, 55.0, 70.8, 81.1, 113.9, 114.6, 127.7, 129.6, 130.0, 133.3, 134.6, 151.7, 154.7, 159.2, 192.8, Anal Calcd for C₁₉H₂₂N₂O₅: C, 63.67; H, 6.19; N, 7.82. Found: C: 63.59, H: 6.21, N: 7.64.

References:

US2003/199511,2003,A1 Location in patent:Page/Page column 70

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References

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