4-(1,3-Dioxolan-2-yl)-2-methoxyphenol → 5-(4-Formyl-2-methoxyphenoxy)pyridine-2-carboxamide

HRID 228286Notes

Reaction equation

HRID 228286 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=1.[O:11]1CCO[CH:12]1[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=1>>[CH:12]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:2]2[CH:3]=[CH:4][C:5]([C:8]([NH2:10])=[O:9])=[N:6][CH:7]=2)=[C:18]([O:23][CH3:24])[CH:17]=1)=[O:11]

Participants

3

Reactant 2

HCID 3463544-(1,3-Dioxolan-2-yl)-2-methoxyphenolHCID 219047545-Fluoropyridine-2-carboxamide

Product 1

HCID 597302085-(4-Formyl-2-methoxyphenoxy)pyridine-2-carboxamideYield 16.2%

Procedure

Using a method similar to Example 388 Part D, using 5-fluoropyridine-2-carboxamide (Example 388 Part C) (0.400 g, 2.85 mmol) and 4-[1,3]dioxolan-2-yl-2-methoxyphenol (Example 386, Part C2) (0.560 g, 2.85 mmol) gives the title compound (0.126 g, 16%): MS ES+ 272.9 (M+H)+: HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.01% TFA/water at 1.0 mL/min. 5-95% over 19 min], tR=11.1 min. 97.2% purity.

Sources & evidence

ORD record
ord-5890c7d03ea7424dbeccef653eca1d23
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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