Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | ||||||
{[ item.p_purity ]} | {[ item.pr_size ]} | Inquiry |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price) ]} |
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]} | {[ item.pr_usastock ]} | in stock Inquiry - | {[ item.pr_chinastock ]} | {[ item.pr_remark ]} in stock Inquiry - | Login | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
CAS No. : | 313735-62-5 | MDL No. : | MFCD09801021 |
Formula : | C6H9BrN2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | HYWPFIXULAMLRZ-UHFFFAOYSA-N |
M.W : | 189.05 | Pubchem ID : | 22329200 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 16h; | A sealable vessel was charged with potassium carbonate (3.76 g, 27.2 mmol), 4-bromo- lH-pyrazole (4.00 g, 27.2 mmol), and 10 mL DMF. To this mixture, 2-iodopropane (3.27 ml, 32.7 mmol) was added and the <n="115"/>vessel sealed. The mixture was heated at 80 C for 16 h and allowed to cool to rt . The mixture was diluted with EtOAc, extracted with water, water, sat NaHCO3, and the organic layer dried over Na2SO4, filtered and evaporated. The mixture was purified via flash chromatography using a EtOAc in CH2C12 gradient. The desired compound (as determined by TLC, 12 stain) was collected as a colorless liquid. | |
To a solution of 4-bromo-1H-pyrazole (20 g, 0.137 mol)in DMF (60 mL) was added NaH (60 wtin oil, 8.2 g, 0.203 mol) at 0 .The resulting mixture was stirred for 30 mins at 0 ,then a solution of 2-iodopropane (25.6 g, 0.15 mol) indioxane (10 mL) was added dropwise at 0 . Theresulting mixture was stirred at RT overnight, quenched with water (50 mL) ,and extracted with EtOAc (30 mL x 3) . The combined organic layers were washedwith brine, dried over Na2SO4, filtered, and concentratedin vacuo. The residue was purified by silica gel column chromatography (7EtOAc in petroleum ether) to give the title compound as a solid.LRMS m/z (M+H) 189.1, 191.1 found, 189.2, 191.2 required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | n--Butyllithium (2.5M in hexanes, 1.38 mL, 3.45 mmol) was added over 15 min to a solution of <strong>[313735-62-5]4-bromo-1-isopropyl-1H-pyrazole</strong> (500 mg, 2.65 mmol) in diethyl ether (10 mL) at -78 C. After 30 min, a solution of tri-n-butylstannane chloride (920 muL, 3.45 mmol) in diethyl ether (1 mL) was added and the resultant reaction mixture was left to stir at -78 C for 1 h, then allowed to warm to ambient temperature. The reaction mixture was diluted with diethyl ether (40 mL) and washed with water (20 mL), then brine (20 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title product as a colourless oil (98 mg, 94%) which was used without further purification. 1H-NMR (CDCl3, 400MHz): 7.46- 7.42 (m, 1 H); 7.28 (t, J = 4.2Hz, 1 H); 4.59-4.43 (m, 1 H); 1.58-1.42 (m, 12 H); 1.39-1.24 (m, 6 H); 1.02-0.77 (m, 15 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 12h;Inert atmosphere; Sealed tube; | b) l-Isopropyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole To a degassed (N2 bubbling) solution of the compound of Intermediate Example 12(a) 4-bromo-l-isopropyl-lH-pyrazole (1.5 g, 7.9 mmol) in 1,4-dioxane (30 ml) were added 4,4,4',4,,5,5,5',5'-octamethyl-2,2*-bi(l,3,2-dioxaborolane) (3 g, 1 1.84 mmol, 1.5 eq.), Pd(dppf)Cl2 (0.64 g, 0.79 mmol, 0.1 eq.) and potassium acetate (1.93 g, 19.74 mmol, 2.5 eq.) using the procedure of Intermediate Example 1(b). The solvent was distilled off to afford the product in 67 % yield (1.2 g). LC-MS (ESI): Calculated mass: 236.12; Observed mass: 237.1 [M+H]+ (rt: 1.41 min). |
67% | With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 12h;Sealed tube; Inert atmosphere; | To a degassed (N2 bubbling) solution of the compound of Intermediate Example 12(a) <strong>[313735-62-5]4-bromo-1-isopropyl-1H-pyrazole</strong> (1.5 g, 7.9 mmol) in 1,4-dioxane (30 ml) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (3 g, 11.84 mmol, 1.5 eq.), Pd(dppf)Cl2 (0.64 g, 0.79 mmol, 0.1 eq.) and potassium acetate (1.93 g, 19.74 mmol, 2.5 eq.) using the procedure of Intermediate Example 1(b). The solvent was distilled off to afford the product in 67% yield (1.2 g). LC-MS (ESI): Calculated mass: 236.12; Observed mass: 237.1 [M+H]+ (rt: 1.41 min). |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,2-dimethoxyethane; water; at 95℃;Inert atmosphere; | To a solution of the product from Step 1 (4.2 g, 0.02 mol) , 4, 4, 4', 4',5, 5, 5', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolane) (11.3 g, 0.04 mol) ,and KOAc (4.38 g, 0.04 mol) in DME/H2O (3: 1, 15 mL) was added Pd(dppf) Cl2 (0.8 g, 1.0 mmol) . The resulting mixture was heated at95 under N2overnight. After cooling to RT, the mixture was filtered and the filtrate wasconcentrated in vacuo. The residue was purified by silica gel columnchromatography (5EtOAc in petroleum ether) to give thetitle compound as an oil. LRMS m/z (M+H) 237.2 found, 237.2 required. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h; | a) 4-Bromo- 1 -isopropyl- 1 H-pyrazoleTo a solution of 4-bromo-l H-pyrazole (5 g, 34 mmol) in DMF (70 ml) were added 2C03 (11.83 g, 85.6 mmol, 2.5 eq.) and 2-bromopropane (6.3 g, 51.36 mmol, 1.5 eq.) and the mixture was stirred at RT for 12 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off and the crude residue was purified by column chromatography (60-120 silica gel, 20 % ethyl acetate in hexane) to afford the product in 89 % yield (5.8 g). 1H NMR (300 MHz, DMSO-i?): delta 8.01 (s, 1H), 7.50 (s, 1H), 4.49-4.43 (m, 1H), 1.38 (d, 6H). |
89% | With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h; | To a solution of 4-bromo-1H-pyrazole (5 g, 34 mmol) in DMF (70 ml) were added K2CO3 (11.83 g, 85.6 mmol, 2.5 eq.) and 2-bromopropane (6.3 g, 51.36 mmol, 1.5 eq.) and the mixture was stirred at RT for 12 h. The mixture was quenched and extracted as in Intermediate Example 5(a). The solvent was distilled off and the crude residue was purified by column chromatography (60-120 silica gel, 20% ethyl acetate in hexane) to afford the product in 89% yield (5.8 g). 1H NMR (300 MHz, DMSO-d6): delta 8.01 (s, 1H), 7.50 (s, 1H), 4.49-4.43 (m, 1H), 1.38 (d, 6H). |
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 10h; | [0001187] To a solution of 4-bromo-lH-pyrazole (2.92 g, 20.0 mmol) in anhydrous DMF (50 mL) was added 2-bromopropane (3.69 g, 30.0 mmol) and potassium carbonate (6.90 g, 50 mmol) at room temperature. The reaction mixture was stirred for 10 h. The mixture was diluted with water (100 mL) and extracted with ethyl acetate (150 mL x 3). The combined organic extracts were washed with brine (150 mL x 2) and dried over anhydrous sodium sulfate. After filtration, the solvent was removed in vacuo and the residue was purified with flash column chromatography on silica gel to give Compound 330A. |
[ 70951-85-8 ]
4-Bromo-1-(tert-butyl)-1H-pyrazole
Similarity: 0.96
[ 1151802-23-1 ]
4-Bromo-1-cyclopropyl-1H-pyrazole
Similarity: 0.93
[ 925224-08-4 ]
2-(4-Bromo-1H-pyrazol-1-yl)acetonitrile
Similarity: 0.84
[ 214614-81-0 ]
4-Bromo-1-(2-hydroxyethyl)pyrazole
Similarity: 0.82
[ 70951-85-8 ]
4-Bromo-1-(tert-butyl)-1H-pyrazole
Similarity: 0.96
[ 1151802-23-1 ]
4-Bromo-1-cyclopropyl-1H-pyrazole
Similarity: 0.93
[ 925224-08-4 ]
2-(4-Bromo-1H-pyrazol-1-yl)acetonitrile
Similarity: 0.84
[ 214614-81-0 ]
4-Bromo-1-(2-hydroxyethyl)pyrazole
Similarity: 0.82