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[ CAS No. 917248-51-2 ] {[proInfo.proName]}

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Chemical Structure| 917248-51-2
Chemical Structure| 917248-51-2
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Product Details of [ 917248-51-2 ]

CAS No. :917248-51-2 MDL No. :MFCD15529863
Formula : C9H8F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HGTYMLFMXKYIQW-UHFFFAOYSA-N
M.W : 186.16 Pubchem ID :53427514
Synonyms :

Safety of [ 917248-51-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 917248-51-2 ]

* 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 [ 917248-51-2 ]

[ 917248-51-2 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 844648-22-2 ]
  • [ 917248-51-2 ]
YieldReaction ConditionsOperation in experiment
97% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 20h; To a stirred solution of <strong>[844648-22-2]5,7-difluoro-2,3-dihydro-4H-chromen-4-one</strong> (2.00 g, 11 mmol, US2005038032) in methanol (30 mL) was added sodium borohydride (0.49 g, 13 mmol) at 0 0C and the mixture was stirred at room temperature for 20 hours. After the mixture was evaporated in vacuo, the residue was treated with water (20 mL) and extracted with ethyl acetate (30 mL x 2). The combined extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford the title compound as a white solid (2.00 g, 97%).1H NMR (CDCI3, 270 MHz) delta: 6.50-6.33 (m, 2H)1 5.07-4.95 (m, 1 H), 4.36-4.18 (m, 2H), 2.16-1.94 (m, 2H) ppm. (-OH was not observed.)
97% With methanol; sodium tetrahydroborate; at 0 - 20℃; for 20h; STEP 1: 5,7-Difluorochroman-4-ol To a stirred solution of <strong>[844648-22-2]5,7-difluoro-2,3-dihydro-4H-chromen-4-one</strong> (2.0 g, 11 mmol, US 2005038032) in methanol (30 mL) was added sodium borohydride (0.49 g, 13 mmol) at 0 C. and the mixture was stirred at room temperature for 20 hours. After the mixture was evaporated in vacuo, the residue was treated with water (20 mL) and extracted with ethyl acetate (30 mL*2). The combined extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford the title compound as a white solid (2.0 g, 97%). 1H NMR (CDCl3, 270 MHz) delta: 6.50-6.33 (m, 2H), 5.07-4.95 (m,1H), 4.36-4.18 (m, 2H), 2.16-1.94 (m, 2H) ppm. (-OH was not observed)
82% With sodium tetrahydroborate; In methanol; at 0℃; for 2h; At a temperature of 0 0C, sodium borohydride (6.4 g, 168 mmol) was added portion-wise to a solution of 5,7-difluoro-2,3-dihydro-4/-/-chromen-4-one (15.5 g, 84.2 mmol) in methanol (150 ml). After a period of 2 hours at 0 0C, the reaction mixture was quenched with saturated ammonium chloride solution (200 ml) and water (200 ml), and extracted with dichloromethane (2 x). The combined organic phases were washed with saturated sodium chloride solution and water and the solvent was evaporated. The colourless residue crystallized in the course of 17 h and was washed with n-heptane. The title compound was isolated in 82 % yield (12.92 g of a colourless solid).
67% With sodium tetrahydroborate; In methanol; at 0℃; for 1h; STEP 8-1: 5,7-Difluoro-3,4-dihydro-2H-chromen-4-ol To a solution of <strong>[844648-22-2]5,7-difluoro-2,3-dihydro-4H-chromen-4-one</strong> (14.2 g, 77.0 mmol, US 20050038032) in methanol (200 mL) was added sodium borohydride (3.50 g, 92.5 mmol) at 0 C. The reaction mixture was stirred at the same temperature for 1 hour, and evaporated to remove methanol. The residue was quenched with water, and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate, and concentrated in vacuum. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1 as an eluent) to afford the title compound as a pale gray solid (9.64 g, 67%). 1H NMR (CDCl3, 270 MHz) delta: 6.47-6.36 (m, 2H), 5.05-4.97 (m, 1H), 4.36-4.20 (m, 2H), 2.16-1.92 (m, 3H) ppm.

  • 3
  • [ 917248-51-2 ]
  • [ 942195-86-0 ]
  • [ 942195-87-1 ]
YieldReaction ConditionsOperation in experiment
With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 20℃; for 6h; STEP 8-2: 4-[(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-N,N,2-trimethyl-1-[(4-methylphenyl)sulfo nyl]-1H-benzimidazole-6-carboxamide To a stirred mixture of 4-hydroxy-N,N,2-trimethyl-1-[(4-methylphenyl)sulfonyl]-1H-benzimidazole-6-carboxamide (110 mg, 0.294 mmol, STEP 7), <strong>[917248-51-2]5,7-difluoro-3,4-dihydro-2H-chromen-4-ol</strong> (164 mg, 0.884 mmol, STEP 8-1) and triphenylphosphine (232 mg, 0.884 mmol) in toluene (5 mL) was added diisopropyl azodicarboxylate (DIAD) (179 mg, 0.884 mmol) at room temperature. The reaction mixture was stirred at room temperature for 6 hours and concentrated in vacuum. The residue was purified by column chromatography on silica gel (ethyl acetate:hexane gradient elution from 1:20 to 10:1) to afford a mixture of the title compound and triphenylphosphine oxide (280 mg, crude) as white solids, which was used in the next step without further purification. 1H NMR (CDCl3, 270 MHz) δ: 7.81 (d, J=8.1 Hz, 2H), 7.51 (s, 1H), 7.31 (d, J=8.1 Hz, 2H), 7.07 (s, 1H), 6.54-6.22 (m, 2H), 5.93 (br. s, 1H), 4.40 (t, J=10.8 Hz, 1H), 4.27 (t, J=10.8 Hz, 1H), 3.15 (br. s, 3H), 3.03 (br. s, 3H), 2.79 (s, 3H), 2.39 (s, 3H), 2.40-2.21 (m, 1H), 2.19-1.73 (m, 1H) ppm. MS (ESI) m/z: 542 (M+H)+, 540 (M-H)-.
  • 4
  • [ 917248-51-2 ]
  • [ 942195-94-0 ]
  • 4-[(5,7-difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-1H-benzimidazole-6-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
STEP 4: 4-4-(5,7-Difluoro-3,4-dihydro-2H-chromen-4-yl)oxy]-2-methyl-1H-benzimidazole-6-carboxylic Acid To a stirred mixture of 1-(1,1-dimethylethyl) 6-methyl 4-hydroxy-2-methyl-1H-benzimidazole-1,6-dicarboxylate (1.50 g, 4.90 mmol, STEP 3), <strong>[917248-51-2]5,7-difluoro-3,4-dihydro-2H-chromen-4-ol</strong> (1.82 g, 9.79 mmol, STEP 8-1 in Example 1) and triphenylphosphine (2.57 g, 9.79 mmol) in toluene (50 mL) was added diisopropyl azodicarboxylate (DIAD) (1.98 g, 4.90 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuum. The residue was dissolved in methanol (20 mL) and tetrahydrofuran (5 mL), and 4M lithium hydroxide aqueous solution (20 mL, 80 mmol) was added to the mixture at room temperature. After stirring for 4 hours at 80 C., the reaction mixture was concentrated in vacuum. The residue was dissolved with water, washed with ethyl acetate, and acidified (pH=6) with 2M hydrochloric acid aqueous solution. The precipitated solid was filtrated, and dried in vacuum to afford the title compound as a white solid (1.67 g, crude), which was used in the next step without further purification. 1H NMR (DMSO-d6, 270 MHz) δ: 7.76 (s, 1H), 7.51 (s, 1H), 6.79 (t, J=10.8 Hz, 1H), 6.66 (t, J=10.8 Hz, 1H), 5.99 (br. s, 1H), 4.39-4.17 (m, 2H), 2.46 (s, 3H), 2.28-2.05 (m, 2H) ppm (-COOH and -NH were not observed). MS (ESI) m/z: 361 (M+H)+, 359 (M-H)-.
  • 5
  • [ 917248-51-2 ]
  • [ 1027098-55-0 ]
YieldReaction ConditionsOperation in experiment
90% With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 5h; To a mixture of <strong>[917248-51-2]5,7-difluorochroman-4-ol</strong> (5.00 g, 26.9 mmol, STEP 1 ) and diphenylphosphoryl azide(6.95 ml, 32.2 mmol) in tetrahydrofuran (50 mL) was added 1 ,8-diazabicyclo[5.4.0]undec-7-ene (5.22 ml,34.9 mmol) dropwise. The reaction mixture was stirred at room temperature for 5 hours. The reaction mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate (300 mL) and water (200 mL). The organic layer was washed with saturated aqueous ammonium chloride solution (50 mL) and brine (50 mL). The organic layer was dried over magnesium sulfate, and concentrated in vacuo.The residue was purified by column chromatography on silica gel (n-hexane / ethyl acetate = 9 / 1 as eluent) to afford the title compound as colorless oil (5.09 g, 90%). 1H NMR (CDCI3, 270 MHz) δ: 6.52-6.39 (m, 2H), 4.93-4.86 (m, 1 H), 4.38-4.28 (m, 1 H), 4.26-4.08 (m, 1 H),2.07-1.99 (m, 2H) ppm.
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 2h; To a solution of Intermediate 34 (3.90 g, 20.3 mmol) in THF (50 mL) were added DPPA (5.28 g, 24.4 mmol) and DBU (3.98 mL, 26.4 mmol) at 0C. The reaction mixture was stirred at r.t. for 2 h, then diluted with H2O (150 mL) and extracted with EtOAc (2 x 150 mL). The organic layer was separated and washed with brine (150 mL), then dried over anhydrous Na2SO4and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 5% EtOAc in hexanes) to afford the title compound (3.50 g, 81%) as a colourless oil. δH(400 MHz, CDCl3) 6.39-6.54 (m, 2H), 4.86-4.94 (m, 1H), 4.28-4.40 (m, 1H), 4.13-4.26 (m, 1H) 1.94-2.09 (m, 2H).
With diphenyl phosphoryl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20℃; for 2h; To a solution of Intermediate 34 (3.90 g, 20.3 mmol) in THF (50 mL) were added DPPA (5.28 g, 24.4 mmol) and DBU (3.98 mL, 26.4 mmol) at 0C. The reaction mixture was stirred at r.t. for 2 h, then diluted with H2O (150 mL) and extracted with EtOAc (2 x 150 mL). The organic layer was separated and washed with brine (150 mL), then dried over anhydrous Na2SO4and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 5% EtOAc in hexanes) to afford the title compound (3.50 g, 81%) as a colourless oil. δH(400 MHz, CDCl3) 6.39-6.54 (m, 2H), 4.86-4.94 (m, 1H), 4.28-4.40 (m, 1H), 4.13-4.26 (m, 1H) 1.94-2.09 (m, 2H).
  • 6
  • [ 917248-51-2 ]
  • [ 917248-52-3 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at 20℃; for 2h; At room temperature, <strong>[917248-51-2]5,7-difluorochroman-4-ol</strong> (10.0 g, 54 mmol) was dissolved portion-wise in thionyl chloride (20 ml) and stirring was continued for 2 hours. The reaction mixture was concentrated several times in the presence of toluene. The title compound was obtained as colourless liquid: 10.95 g, 99 % yield.
  • 7
  • [ 844648-16-4 ]
  • [ 917248-51-2 ]
  • 8
  • [ 844648-19-7 ]
  • [ 917248-51-2 ]
  • 9
  • [ 917248-51-2 ]
  • [ 1092938-65-2 ]
  • 10
  • [ 917248-51-2 ]
  • [ 1092938-70-9 ]
  • 11
  • [ 917248-51-2 ]
  • [ 1092938-74-3 ]
  • 12
  • [ 2713-34-0 ]
  • [ 917248-51-2 ]
  • 13
  • [ 917248-51-2 ]
  • [ 886762-87-4 ]
  • 14
  • [ 917248-51-2 ]
  • [ 1270294-05-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
Multi-step reaction with 3 steps 1: Novozym 435 / 2-methoxy-2-methylpropane / 3 h / 20 °C 2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3: sodium tetrahydridoborate; methanol; lithium hydroxide monohydrate / 1 h / 20 °C
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