Potassium Carbonate → 6-bromo-4-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-quinoline

HRID 1890923Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:13][N:14]1[CH:18]=[N:17][N:16]=[C:15]1[SH:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][CH:3]=[C:2]2[S:19][C:15]1[N:14]([CH3:13])[CH:18]=[N:17][N:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A capped vial was charged with 4-chloro-6-bromoquinoline (500 mg, 2.06 mmol), 4-methyl-4H-[1,2,4]triazole-3-thiol (238 mg, 2.06 mmol), potassium carbonate (427 mg, 3.09 mmol), and DMF (5 mL). The reaction mixture was stirred at 60° C. for 18 h then at 90° C. for another 24 h, and cooled to room temperature. The reaction mixture was poured onto water (50 mL), and the resulting precipitate was filtered, washed with water and dried in a vacuum oven at 70° C. overnight to provide 600 mg of 6-bromo-4-(4-methyl-4H-[1,2,4]triazol-3-ylsulfanyl)-quinoline as a white solid (91% yield): 1H NMR (DMSO-d6) δ 3.63 (s, 3H), 6.90 (d, 1H), 8.02 (m, 2H), 8.40 (d, 1H), 8.74 (d, 1H), 8.92 (s, 1H); MS (m/z) 321, 323 [M+H]+.

Workup

waitat 90° C. for another 24 h
temperaturecooled to room temperature
additionThe reaction mixture was poured onto water (50 mL)
filtrationthe resulting precipitate was filtered
washwashed with water
customdried in a vacuum oven at 70° C. overnight

Sources & evidence

ORD record: ord-7df65c81922349318523fbe866a56914
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507489B2

Reaction notes

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