(2-Methylpyridin-4-yl)methanol → 2,6-Difluoro-3-[(2-methyl-4-pyridinyl)methoxy]benzenecarboxamide

HRID 415608Notes

Reaction equation

HRID 415608 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([NH2:12])=[O:11].O[CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=1>>[F:1][C:2]1[C:7]([O:8][CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([NH2:12])=[O:11]

Participants

3

Reactant 2

HCID 9942144(2-Methylpyridin-4-yl)methanolHCID 451201362,6-Difluoro-3-hydroxybenzamide

Product 1

HCID 594029902,6-Difluoro-3-[(2-methyl-4-pyridinyl)methoxy]benzenecarboxamideYield 34%

Procedure

Synthesised from 2,6-difluoro-3-hydroxybenzenecarboxamide according to Method C, scheme 3. The required building block, 4-hydroxymethyl-2-methylpyridine, was synthesised according to the literature method, shown in Scheme 23 (Ragan, J. A., Jones, B. P., Meltz, C. N., Teixeira J. J. Jr.; Synthesis 2002, 483-486. Yield 34%, mp 185-186° C., HPLC-MS (method 1): m/z 279 [M+H]+, Rt=2.50 min.

Workup

  1. customSynthesis 2002, 483-486

Sources & evidence

ORD record
ord-5ee878e59a1c44468ad7e53d661af8aa
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

Loading…