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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List 5-bromo-1-methyl-1,2,4-triazole
16681-72-4

5-bromo-1-methyl-1,2,4-triazole synthesis

1synthesis methods
1-METHYL-1,2,4-TRIAZOLE

6086-21-1

5-bromo-1-methyl-1,2,4-triazole

16681-72-4

General procedure for the synthesis of 5-bromo-1-methyl-1H-1,2,4-triazole from 1-methyl-1H-1,2,4-triazole: 1.6 M n-BuLi (8.70 mL, 13.86 mmol) was slowly added to a mixed solution of 1-methyl-1H-1,2,4-triazole (1.0 mL, 13.20 mmol) and THF (100 mL) at -78 °C. 13.86 mmol). After 45 min of reaction, 1,2-dibromo-1,1,2,2-tetrafluoroethane (1.76 mL, 14.52 mmol) was added, and then the reaction mixture was slowly warmed to room temperature and stirring was continued for 2 hours. After completion of the reaction, the reaction solution was diluted with EtOAc (200 mL), washed sequentially with water (150 mL) and brine (150 mL), the organic phase was dried with MgSO4, filtered and concentrated to afford 5-bromo-1-methyl-1H-1,2,4-triazole (1.37 g, 8.46 mmol, 64% yield). The product was confirmed by 1H NMR (CDCl3): δ 3.82 (s, 3H), 7.78 (s, 1H). LC/MS analysis showed that the m/z calculated value [C3H4BrN3(M+H)+] was 162.0 and the measured value was 161.9.

6086-21-1 Synthesis
1-METHYL-1,2,4-TRIAZOLE

6086-21-1
195 suppliers
$6.00/1g

5-bromo-1-methyl-1,2,4-triazole

16681-72-4
85 suppliers
$17.00/250mg

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Yield: 64%

Reaction Conditions:

Stage #1:1-methyl-1H-1,2,4-triazole with n-butyllithium in tetrahydrofuran at -78; for 0.75 h;
Stage #2: with 1,2-dibromo-1,1,2,2-tetrafluoroethane in tetrahydrofuran at 20; for 2 h;
Stage #3: with water;ethyl acetatemore than 3 stages;

Steps:

133.A; 133.C
Example 133.; Preparation of 8-(1-ethyl-propyl)-3-[3-methoxy-5-(2-methyl-2H-[1,2,4]triazol-3-yl)- thiophen-2-yl]-2,6-dimethyl-imidazo[1,2-b]pyridazine.; A. 5-Bromo-1-methyl-1H-[1,2,4]triazole.; EPO To a -78 °C solution of l-methyl-1H-[1,2,4]triazole (1.0 mL, 13.20 mmol) and TΗF (100 mL) is added 1.6 M n-BuLi (8.70 mL, 13.86 mmol). After 45 minutes 1,2- dibromo-l,1,2,2-tetrafluoro-ethane (1.76 mL, 14.52 mmol) is added, the solution is warmed to ambient temperature and stirred for 2 hours. The solution is diluted with EtOAc (200 mL), washed with water (150 mL), brine (150 mL), dried over MgSO4, filtered and concentrated to furnish the title compound (1.37 g, 8.46 mmol, 64%). 1H NMR (CDCl3) δ 3.82 (s, 3H), 7.78 (s, 1H). LC/MS (m/z): calcd. for C3H4BrN3 (M+H)+: 162.0; found: 161.9.

References:

ELI LILLY AND COMPANY WO2006/102194, 2006, A1 Location in patent:Page/Page column 117-118

5-bromo-1-methyl-1,2,4-triazole Related Search:

Sulfathiazole 3,5-DIBROMO-1-METHYL-1H-1,2,4-TRIAZOLE