Ethylene glycol dioxane → 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide

HRID 2174282Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[N:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][N:17]=3)[N:10]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[N:9]=2)[CH:3]=1.[Cu][C:27]#[N:28].C(O)C[OH:31].O1CCOCC1>[Cl-].[Na+].O>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[C:11]([C:13]2[S:14][CH:15]=[CH:16][N:17]=2)=[N:12][C:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][N:5]=2)[C:27]([NH2:28])=[O:31])=[N:9]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirring suspension of 2-(3-(4-bromopyridin-2-yl)-1-(2-fluorobenzyl)-1H-1,2,4-triazol-5-yl)thiazole (I-36, 1 equiv) in ethylene glycol-dioxane (approx. 4:1) in a sealed tube was added copper(I) cyanide (3 equiv). The resultant reaction mixture was heated at 100° C. for 24 hr and then cooled to room temperature, treated with brine and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified using SiO2 chromatography (ethyl acetate/hexanes) to afford 2-(1-(2-fluorobenzyl)-5-(thiazol-2-yl)-1H-1,2,4-triazol-3-yl)isonicotinamide as a solid in 11% yield.

Workup

customThe resultant reaction mixture
temperaturecooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated
custompurified

Sources & evidence

ORD record: ord-462b5e32433448ea8a0ccb44da82d892
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061030B2

Reaction notes

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