5-Fluoropyridine-2-carboxamide → 5-(4-Formyl-2-methylphenoxy)pyridine-2-carboxamide

HRID 130835

Reaction equation

HRID 130835 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]([CH3:23])[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]([CH3:23])[CH:17]=1)=[O:11]

Participants

3

Reactant 2

HCID 219047545-Fluoropyridine-2-carboxamideHCID 552555104-[1,3]Dioxolan-2-yl-2-methylphenol

Product 1

HCID 597302035-(4-Formyl-2-methylphenoxy)pyridine-2-carboxamideYield 35.5%

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-methylphenol (Example 388, Part C2) (0.514 g, 2.85 mmol) gives the title compound (0.259 g): TLC [silica gel 60 F254, 30% ethyl acetate in dichloromethane] Rf=0.20; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), 0.1% TFA/acetonitrile in 0.1% TFA/water at 1.0 mL/min, 5-95% over 19 min], tR=12.1 min, 73.1% purity.

Sources & evidence

ORD record
ord-1ab62a83a73c40508f7a97e39d07375e
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Linked notes

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