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Chemical Structure| 1262035-61-9 Chemical Structure| 1262035-61-9

Structure of 1262035-61-9

Chemical Structure| 1262035-61-9

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Product Details of [ 1262035-61-9 ]

CAS No. :1262035-61-9
Formula : C6H7BrN2
M.W : 187.04
SMILES Code : BrC1=CN=CN1C2CC2
MDL No. :MFCD16250307
InChI Key :YIXZAZVJTMUAKO-UHFFFAOYSA-N
Pubchem ID :58102920

Safety of [ 1262035-61-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 1262035-61-9 ]

* 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.

  • Downstream synthetic route of [ 1262035-61-9 ]

[ 1262035-61-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 135207-17-9 ]
  • [ 1262035-61-9 ]
YieldReaction ConditionsOperation in experiment
37% With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In dichloromethane; at 5 - 10℃; for 2h; Step 2 Cyclopropyl-1H-imidazole (1.18 g, 10.9 mmol) was dissolved in methylene chloride (0.1 M), cooled to 5-10 C., and 1,3-dibromo-5,5-dimethylhydantoin (1.59 g, 5.57 mmol) was added. The temperature was maintained between 5-10 C. and the reaction was stirred for 2 hours. Solvent was removed from the reaction mixture under reduced pressure, and the residue was purified by column chromatography (eluding with 1%-7% methanol in methylene chloride, 5% methanol/methylene chloride) to afford 620 mg (37% yield) of 5-bromo-1-cyclopropyl-1H-imidazole.
1.21 g With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In dichloromethane; at 5℃; Intermediate lc' 5-Bromo- 1-cyclopropyl- lH-imidazole In a 350 mL four-necked flask, 1-cyclopropyl- lH-imidazole (2.58 g, 23.9 mmol, Eq: 1.00) was combined with DCM (100 ml) to give a colorless solution. l,3-Dibromo-5,5- dimethylimidazolidine-2,4-dione (3.48 g, 12.2 mmol, Eq: 0.51), dissolved in dichloromethane (100 ml) was added drop wise at 5C and the reaction mixture stirred at 5C for 2.5hr. Work up: The reaction mixture was quenched with 100ml Na2S03 sol. and extracted with DCM (2X200ml). The organic layers were washed with H20/NaCl sol, dried over Na2S04 and concentrated i. V. The crude product was purified by flash chromatography (silica gel, 120g, 25% to 100% EtOAc in heptane) to give 1.21g of the title compound as colorless oil. MS (ESI): 187.9/189.1 [M+H]+.
1.21 g With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In dichloromethane; at 5℃; for 2.5h;Inert atmosphere; In a 350 mL four-necked flask, 1-cyclopropyl-1H-imidazole (2.58 g, 23.9 mmol, Eq: 1.00) was combined with DCM (100 ml) to give a colorless solution. 1,3-Dibromo-5,5-dimethylimidazolidine-2,4-dione (3.48 g, 12.2 mmol, Eq: 0.51), dissolved in dichloromethane (100 ml) was added dropwise at 5 C. and the reaction mixture stirred at 5 C. for 2.5 hr. Work up: The reaction mixture was quenched with 100 ml Na2SO3 sol. and extracted with DCM (2*200 ml). The organic layers were washed with H2O/NaCl sol, dried over Na2SO4 and concentrated i. V. The crude product was purified by flash chromatography (silica gel, 120 g, 25% to 100% EtOAc in heptane) to give 1.21 g of the title compound as colorless oil. MS (ESI): 187.9/189.1 [M+H]+.
  • 2
  • [ 870703-61-0 ]
  • [ 1262035-61-9 ]
  • [ 1262044-15-4 ]
  • [ 1262044-16-5 ]
YieldReaction ConditionsOperation in experiment
A. Preparation of N-6-(1-cyclopropyl-1H-imidazol-5-yl)pyridin-2-yl)-4-(quinolin-3-yl)picolinamide Steps 1 and 2: To a stirred solution of <strong>[1262035-61-9]5-bromo-1-cyclopropyl-1H-imidazole</strong> (780 mg, 1.90 mmol), in tetrahydrofuran (3 mL) at -78 C. was added n-butyllithium (911 muL 2.5 M solution, 2.28 mmol) and the reaction mixture was stirred for 30 minutes at -78 C. A solution of zinc bromide (ZnBr2, (641 mg, 2.85 mmol, dried under vacuum at 100 C. for 3 hours) in tetrahydrofuran (3 mL) was added, the mixture warmed to room temperature and stirred an additional 2.5 hours. A solution of 6-(di-Boc-amino)-2-bromopyridine and Pd(PPh3)4 in 3 mL tetrahydrofuran was added to the reaction via cannula and the mixture was stirred overnight. The reaction was concentrated under reduced pressure and the residue was purified by flash chromatography (5% methanol in methylene chloride, gradient flash: 4%?10% methanol in methylene chloride). The product was isolated as mixture of the mono- and bis-Boc protected 6-(1-cyclopropyl-1H-imidazol-5-yl)pyridin-2-amine. This mixture was used directly in the next step
  • 3
  • [ 1262035-61-9 ]
  • [ 1450738-74-5 ]
  • 4
  • [ 1262035-61-9 ]
  • [ 105-07-7 ]
  • [ 1450739-60-2 ]
YieldReaction ConditionsOperation in experiment
81 mg Step 1 4-[(3-Cyclopropyl-3H-imidazol-4-yl)-hydroxy-methyl]-benzonitrile In a 10 mL two-necked flask, 5-bromo-l-cyclopropyl-lH-imidazole (intermediate lc', 107 mg, 572 muiotaetaomicron, Eq: 1.00) was combined with DCM (3 ml) to give a colorless solution. Isopropyl magnesium chloride, lithium chloride complex (484 mu, 629 muiotaetaomicron, Eq: 1.1) was added within 2min (white precipitate). After stirring for 80min., the reaction flask was cooled to 0C, and a solution of 4-formylbenzonitrile (90.0 mg, 686 muiotaetaomicron, Eq: 1.2) in DCM (2 ml) was added dropwise. The reaction was allowed to proceed at rt for 2 h when TLC showed that the reaction was complete. Work up: The reaction mixture was quenched with 3ml sat. NH4C1, then poured into 6ml sat. NaHC03 and extracted with DCM (2X 25ml). The organic layers were washed with brine, combined, dried over Na2S04, and concentrated i. V. The crude material was purified by flash chromatography (silica gel, 20g, 2% to 10% MeOH in DCM) to yield 81 mg of the title compound as white foam. MS (ESI): 240.1 [M+H]+.
81 mg In a 10 mL two-necked flask, <strong>[1262035-61-9]5-bromo-1-cyclopropyl-1H-imidazole</strong> (intermediate 1c', 107 mg, 572 mumol, Eq: 1.00) was combined with DCM (3 ml) to give a colorless solution. Isopropyl magnesium chloride, lithium chloride complex (484 mul, 629 mumol, Eq: 1.1) was added within 2 min (white precipitate). After stirring for 80 min., the reaction flask was cooled to 0 C., and a solution of 4-formylbenzonitrile (90.0 mg, 686 mumol, Eq: 1.2) in DCM (2 ml) was added dropwise. The reaction was allowed to proceed at rt for 2 h when TLC showed that the reaction was complete. Work up: The reaction mixture was quenched with 3 ml sat. NH4Cl, then poured into 6 ml sat. NaHCO3 and extracted with DCM (2*25 ml). The organic layers were washed with brine, combined, dried over Na2SO4, and concentrated i. V. The crude material was purified by flash chromatography (silica gel, 20 g, 2% to 10% MeOH in DCM) to yield 81 mg of the title compound as white foam. MS (ESI): 240.1 [M+H]+.
  • 5
  • [ 1262035-61-9 ]
  • 3-methoxy-1-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole-4-carboxamide [ No CAS ]
  • N-(3-(1-cyclopropyl-1H-imidazol-5-yl)phenyl)-3-methoxy-1-methyl-1H-pyrazole-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With DPPF Pd G3; caesium carbonate; In 1,4-dioxane; water; at 120℃; for 1h;Inert atmosphere; Microwave irradiation; Sealed tube; A microwave vial was charged with <strong>[1262035-61-9]5-bromo-1-cyclopropyl-1H-imidazole</strong> (40 mg, 0.21 mmol), 3-methoxy-1-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)- 1H-pyrazole-4-carboxamide (75 mg, 0.21 mmol), cesium carbonate (137 mg, 0.42 mmol) and Pd(dppf) G3 (20 mg, 0.02 mmol). Dioxane (1.5 mL) and water (75 muL) were added. The vial was purged with N2, sealed and irradiated in a biotage microwave at 120 C for 1 h. After this time he volatiles were removed under reduced pressure and the resulting black residue was taken up in DMSO and subjected to prep-HPLC (using a Sunfire Prep C18 OBD, 5mum 30x50mm column and using 95% water/5% MeCN (initial conditions) to 50% water/50% MeCN over 20 minutes in 0.1% TFA as the mobile phase at a flow rate of 50 mL/min). The fractions containing product were combined, evaporated to dryness and the resulting residue was dissolved in DCM (20 mL) and washed with satd. NaHCO3 (10 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated to give the title compound (28 mg, 40%) as a white solid. 1H NMR (400 MHz, CDCl3) d ppm 8.53 (s, 1H), 8.01 (t, J=1.8 Hz, 1H), 7.79 (s, 1H), 7.57 (d, J=0.8 Hz, 1H), 7.46 - 7.41 (m, 1H), 7.36 (t, J=7.8 Hz, 1H), 7.25 (td, J=1.4, 7.8 Hz, 1H), 7.11 (d, J=1.3 Hz, 1H), 4.09 (s, 3H), 3.78 (s, 3H), 3.42 (tt, J=3.7, 7.2 Hz, 1H), 1.06 - 0.98 (m, 2H), 0.90 - 0.82 (m, 2H). MS (ESI): 338.1 [M + H]+.v
 

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