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Product Details of [ 1357095-18-1 ]

CAS No. :1357095-18-1 MDL No. :MFCD22205821
Formula : C9H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :HDASBCPGRAIAKQ-UHFFFAOYSA-N
M.W : 228.09 Pubchem ID :66716059
Synonyms :

Safety of [ 1357095-18-1 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1357095-18-1 ]

* 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 [ 1357095-18-1 ]

[ 1357095-18-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 36953-42-1 ]
  • [ 2516-33-8 ]
  • [ 1357095-18-1 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydride; In N,N-dimethyl-formamide; at 20 - 100℃; for 3h;Inert atmosphere; Example 42 5-Cyclopropyl-4-cyclopropylmethoxy-pyridine-2-carboxylic acid (3-thiazol-2-yl- oxetan-3-yl)-amide a) 3-Bromo-4-cyclopropylmethoxy-pyridine To a solution of <strong>[36953-42-1]3-bromo-4-chloropyridine</strong> (CAN 36953-42-1, 5 g, 26.0 mmol) in dry DMF (60 ml) under an argon atmosphere at room temperature was added cyclopropylmethanol (CAN 2516-33-8, 1.97 g, 27.3 mmol) and sodium hydride 60% (1.09 g, 27.3 mmol) by portions. The resulting reaction was stirred at room temperature until gas evolution stopped. The reaction mixture was then stirred at 100C for 3h.The reaction was cooled down to room temperature, quenched by addition of water and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethylacetate, extracted with 1.0M aqueous solution sodium bicarbonate, organic phase dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the titled compound (5.8 gr, 98%) as a light yellow oil. MS (ESI, m/z) 228.1 (M+H+).
87% With sodium hydride; In N,N-dimethyl-formamide; at 100℃; for 3h;Inert atmosphere; To a solution of <strong>[36953-42-1]3-bromo-4-chloropyridine</strong> (CAS 36953-42-1) (8 g, 41.6 mmol, Eq: 1.00) in dry DMF (100 mL) under argon atmosphere at RT was added cyclopropylmethanol (CAS 2516-33-8) (3.15 g, 3.45 mL, 43.6 mmol, Eq: 1.05) and by portions NaH (1.75 g, 43.6 mmol, Eq: 1.05). The resulting reaction was stirred at RT until gas evolution stopped. The reaction mixture was then stirred at 100C for 3 h and controlled by TLC. The reaction was cooled down to RT, quenched by addition of water and the mixture concentrated in vacuo. The residue was redissolved in ethyl acetate, extracted with aqueous NaHC03 1M, the organic phase dried over Na2S04, filtered and evaporated down to dryness. Flash chromatography with a 120 g Si02 column, with an eluent mixture of heptane and ethyl acetate to give 8.25 g of light yellow oil (Yield: 87%). MS (ESI, m/z): 228.2 (M).
To an ice-cold solution of cyclopropylmethanol (0.562 g, 7.79 mmol) in THF (Volume: 15.06 ml) was added NaH (0.270 g, 6.76 mmol). The reaction was stirred at room temperature for 30 min, and then cooled to 0 C. To this mixture was added 3- bromo-4-chloropyridine (1 g, 5.20 mmol). The resulting mixture was refluxed for 16 hours, cooled to room temperature, and quenched with water. The mixture was evaporated to remove the THF and then extracted with DCM (2X). The combined organic layers were washed with water and brine, dried, and concentrated to give an oil. The oil was purified by silica gel chromatography (hexane: ethyl acetate 50:50) to afforded the title compound as a colorless oil. MS (ES): m/z = 229 [M+H]+. Intermediate 66 was used in the synthesis of Example 255.
  • 2
  • [ 1065010-87-8 ]
  • [ 1357095-18-1 ]
  • [ 1613238-49-5 ]
YieldReaction ConditionsOperation in experiment
78.5% With palladium diacetate; caesium carbonate; catacxium A In water; toluene at 115℃; for 16h; 42.b 3-Cyclopropyl-4-cyclopropylmethoxy-pyridine 3-Cyclopropyl-4-cyclopropylmethoxy-pyridine To a solution of 3-Bromo-4-cyclopropylmethoxy-pyridine (Example 42a, 4.1 g, 18.0 mmol) in a mixture of toluene (55 ml) and water (6.5 ml) was added potassium cyclopropyltrifluoroborate (CAN 1065010-87-8, 2.79 g, 18.9 mmol), palladium(II) acetate (80.7 mg, 360 μιηο), butyldi-l-adamantylphosphine (CAN 321921-71-5, 193 mg, 539 μιηο) and cesium carbonate (14.6 g, 44.9 mmol). The reaction mixture was stirred at 115°C for 16h, cooled down to room temperature and filtered through a pad of celite. The filtrate was poured into a separatory funnel, diluted with ethylacetate and extracted with water. The organic phase was collected, dried over sodium sulfate and evaporated down to dryness. The crude was purified by flash chromatography on silica eluting with a heptane/(solution 3% triethylamine in ethylacetate) gradient to yield the title compound (2.67gr, 78.5%) as a yellow oil. MS (ESI, m/z): 190.3 (M+H+).
68% With palladium diacetate; caesium carbonate; catacxium A In water; toluene at 125℃; for 7h; 1.b b) 3-cyclopropyl-4-(cyclopropylmethoxy)pyridine To a solution of 3-bromo-4-(cyclopropylmethoxy)pyridine (8.1 g, 35.5 mmol, Eq: 1.00) in a mixture of toluene (150 mL) and water (18 mL) was added potassium cyclopropyltrifluoroborate (CAS 1065010-87-8) (5.52 g, 37.3 mmol, Eq: 1.05), Cs2C03 (23.1 g, 71.0 mmol, Eq: 2.0), butyldi-l-adamantylphosphine (382 mg, 1.07 mmol, Eq: 0.03) and Pd(OAc)2 (159 mg, 710 μιηο, Eq: 0.02). The reaction mixture was stirred at 125°C for 7 h. Reaction mixture was cooled down and poured into a separatory funnel, ethyl acetate and water were added. After extraction of the mixture, the organic phase was collected, dried over Na2S04 and evaporated down to dryness. Flash chromatography with a 120 g Si02 column, and an eluent mixture of heptane and ethyl acetate gave 4.6 g of the desired product (Yield 68%). MS (ESI, m/z) 190.3 (MH+).
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