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Methyl 4-((tert-butoxycarbonyl)aMino)nicotinate synthesis

3synthesis methods
-

Yield:280115-84-6 96%

Reaction Conditions:

with N-iodo-succinimide;potassium carbonate at 20; for 1 h;

Steps:

8.8B 8B. Formula 504 where R1, R3 and R4 are H; W, Y and Z are -C=: and X is-N=:

To a solution of methanol (100 mL) and N-Boc-4-amino-3-pyridine carboxyaldehyde (8.3 g, 37.3 [MMOL),] were added N-iodosuccinimide (21.0 g, 93.4 [MMOL)] and potassium carbonate (12.9 g, 93.4 [MMOL)] at room temperature. The mixture was stirred for 1 hour and then poured into a saturated Na2S203 solution (100 mL). After further dilution with water (100 mL) the mixture was extracted with dichloromethane (3 X 100 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to give the pure desired methyl ester product, 4-tert- butoxycarbonylamino-nicotinic acid methyl ester (9.0 g, 96%). MS (CI) m/e: 253.

References:

WO2003/103575,2003,A2 Location in patent:Page 74