Sodium Acetate → 4-(thiazolo[5,4-b]pyridine-2-yl)-1-(2-chlorophenyl)-5-methyl-1H-[1,2,3]triazole

HRID 601673Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([CH3:13])=[C:11](I)[N:10]=[N:9]1.[N:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[S:17][CH:16]=1.C([O-])(=O)C.[Na+]>CN(C=O)C.O>[N:15]1[C:23]2[C:18](=[N:19][CH:20]=[CH:21][CH:22]=2)[S:17][C:16]=1[C:11]1[N:10]=[N:9][N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:12]=1[CH3:13]

Participants

Conditions

Temperature: 140 °C

Procedure

Under nitrogen atmosphere, 344 mg of 1-(2-chlorophenyl)-4-iodo-5-methyl-[1,2,3]-triazole and 276 mg of thiazolo(5,4-b)pyridine (B. Stanovnik, Synthesis, 1974, 120) were dissolved in 3 ml of DMF. Then, 100 mg of sodium acetate and 103 mg of Herrman catalyst were added, and the mixture was stirred at 140° C. for 8 hours. After diluting the reaction solution with water, the resultant was extracted with chloroform. Organic layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The residues obtained by distilling out the solvents were separated and purified by thin-layer silicagel column chromatography (ethyl acete/hexane=1/1) to obtain 30 mg of the above compound as a white solid.

Workup

extractionthe resultant was extracted with chloroform
washOrganic layer was washed with saturated saline solution
dry with materialdried with anhydrous sodium sulfate
customThe residues obtained
distillationby distilling out the solvents
customwere separated
custompurified by thin-layer silicagel column chromatography (ethyl acete/hexane=1/1)

Sources & evidence

ORD record: ord-5b3301b88e2c4c008ac9c0ca8bedb795
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902369B2

Reaction notes

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