Dimethylformamide → 3-Cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine

HRID 1294224

Reaction equation

HRID 1294224 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[CH:15][C:14]=2[O:21][CH3:22])[N:10]=1.Cl[C:25]1[C:30]([C:31]#[N:32])=[CH:29][CH:28]=[CH:27][N:26]=1.CN(C)C=O.[H-].[Na+]>O>[C:31]([C:30]1[C:25]([O:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:9]3[N:10]=[C:6]([C:2]4[O:1][CH:5]=[CH:4][CH:3]=4)[O:7][C:8]=3[CH3:23])=[C:14]([O:21][CH3:22])[CH:15]=2)=[N:26][CH:27]=[CH:28][CH:29]=1)#[N:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 810792-ChloronicotinonitrileHCID 537700494-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]-3-methoxybenzyl alcohol

Product 1

HCID 688834623-Cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridineYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxyphenyl]methanol (5.00 g), 2-chloro-3-cyanopyridine (2.65 g) and N,N-dimethylformamide (150 mL) was added sodium hydride (60%, oil, 0.70 g) at room temperature and the mixture was stirred for 15 hrs. Water was added to the reaction mixture and the precipitated crystals were collected by filtration to give crystals (6.60 g, yield 99%) of 3-cyano-2-[4-[[2-(2-furyl)-5-methyl-4-oxazolyl]methoxy]-3-methoxybenzyloxy]pyridine. Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 137-138° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-46f348360ef547e3962363edd062eefb
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Linked notes

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