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Chemical Structure| 946000-13-1
Chemical Structure| 946000-13-1
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Product Details of [ 946000-13-1 ]

CAS No. :946000-13-1 MDL No. :MFCD13189516
Formula : C11H15BrN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CGHVUYZFVGMPKA-UHFFFAOYSA-N
M.W : 287.15 Pubchem ID :59683608
Synonyms :

Safety of [ 946000-13-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 946000-13-1 ]

* 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.

  • Upstream synthesis route of [ 946000-13-1 ]
  • Downstream synthetic route of [ 946000-13-1 ]

[ 946000-13-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 207799-10-8 ]
  • [ 74-88-4 ]
  • [ 946000-13-1 ]
YieldReaction ConditionsOperation in experiment
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of te/7-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
Synthesis of Compound 357tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160)To a solution of tert-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C was added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane was added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction was then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The combined organic phases were dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS ?r 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; for 16 h;
tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of ter/-butyl carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS tr 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
76%
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 16 h;
Synthesis of Compound 357; tert-Butyl (4-bromo-pyridin-2-yl)-methyl-carbamate (160); To a solution of tert-buty\\ carbamate 155 (300 mg, 1.10 mmol) in THF (5 mL) at 0°C is added sodium hydride (53 mg, 1.32 mmol, 60percent dispersion in mineral oil) in one portion. After stirring 15 minutes, iodomethane is added (82 μL, 1.32 mmol) and the reaction mixture warmed to RT and stirred 16 h. The reaction is then quenched with 5percent citric acid (10 mL) and extracted into EtOAc (2 x 10 mL). The EPO <DP n="298"/>combined organic phases are dried over Na2SO4 and purified by column chromatography (70percent EtOAc in heptane) to give the title compound. Yield: 240 mg (76percent). LC/MS ?r 1.62 min. MS(ES+) m/z 289, 287 (M+H), 233, 231 (M-C(CH3)3+H).
0.25 g
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 1 h;
Step a. To a solution of teit-butyl (4-bromopyridin-2-yl)carbamate (0.25g, 0.915 mmol) in DMF (5 ml) was added NaH (60percent in oil) (0.073g, 1.83 mmol) at 0°C. The reaction mixture was stirred at 0°C for 15 min. Methyl iodide (0.26g, 1.37 mmol) was added to the reaction mixture at 0°C. The reaction mixture was stirred at rt for 1 h, poured into ice cold water (20 ml) and extracted with EtOAc (2 x 15 ml). The organic layer was washed with brine (20 ml). The organic phase was collected, dried over Na2SC>4, filtered and concentrated under reduced pressure yielding tert-butyl (4-bromopyridin-2-yl)(methyl)carbamate (0.25g, 0.87 mmol). This material was directly used for the next step without further purification. LCMS: Method A, 2.50 min, MS: ES+ 230.9; 232.9 (M-56)

Reference: [1] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 296-297
[2] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 208
[3] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 296-297
[4] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 296-297
[5] Patent: WO2016/46530, 2016, A1, . Location in patent: Page/Page column 79
  • 2
  • [ 18437-58-6 ]
  • [ 946000-13-1 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 3
  • [ 22282-99-1 ]
  • [ 946000-13-1 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 4
  • [ 5470-66-6 ]
  • [ 946000-13-1 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
  • 5
  • [ 30766-03-1 ]
  • [ 946000-13-1 ]
Reference: [1] Patent: WO2008/57469, 2008, A1,
[2] Patent: WO2008/57468, 2008, A1,
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