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Chemical Structure| 1260878-78-1 Chemical Structure| 1260878-78-1

Structure of 1260878-78-1

Chemical Structure| 1260878-78-1

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Product Details of [ 1260878-78-1 ]

CAS No. :1260878-78-1
Formula : C6H3ClFNO
M.W : 159.55
SMILES Code : O=CC1=NC=CC(Cl)=C1F
MDL No. :MFCD16249577
InChI Key :NFGGDPYDUVFSCH-UHFFFAOYSA-N
Pubchem ID :72212767

Safety of [ 1260878-78-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 1260878-78-1 ]

* 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 [ 1260878-78-1 ]

[ 1260878-78-1 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 1260878-78-1 ]
  • [ 1422511-24-7 ]
  • 2
  • [ 1260878-78-1 ]
  • C9H10ClFN2 [ No CAS ]
  • 3
  • [ 1260878-78-1 ]
  • [ 1422510-27-7 ]
  • 4
  • [ 1260878-78-1 ]
  • [ 1422510-25-5 ]
  • 5
  • [ 1260878-78-1 ]
  • [ 1422510-46-0 ]
  • 6
  • [ 1260878-78-1 ]
  • [ 1422510-44-8 ]
  • 7
  • [ 1260878-78-1 ]
  • [ 1422510-59-5 ]
  • 8
  • [ 1260878-78-1 ]
  • C10H12ClFN2 [ No CAS ]
  • 9
  • [ 1260878-78-1 ]
  • [ 1422510-60-8 ]
  • 10
  • [ 1260878-78-1 ]
  • [ 1422510-58-4 ]
  • 11
  • [ 1260878-78-1 ]
  • [ 1422508-84-6 ]
  • 12
  • [ 1260878-78-1 ]
  • methyl ((10R,14S)-14-(4-(4-chloro-3-fluoro-2-pyridinyl)-2-oxotetrahydro-1(2H)-pyrimidinyl)-10-methyl-9-oxo-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl)carbamate hydrochloride [ No CAS ]
  • 13
  • [ 1260878-78-1 ]
  • methyl ((3R,7S)-7-(((3R)-3-((tert-butyl(dimethyl)silyl)oxy)-3-(4-chloro-3-fluoropyridin-2-yl)propyl)amino)-3-methyl-2-oxo-9-((2-(trimethylsilyl)ethoxy)methyl)-1,2,3,4,5,6,7,9-octahydro-11,8-(azeno)-1,9-benzodiazacyclotridecin-14-yl)carbamate [ No CAS ]
  • 14
  • [ 1260878-78-1 ]
  • [ 1422511-05-4 ]
  • 15
  • [ 1260878-78-1 ]
  • methyl N-[(10R,14S)-14-[(6R)-6-(4-chloro-3-fluoropyridin-2-yl)-2-oxo-1,3-oxazinan-3-yl]-10-methyl-9-oxo-8,16,18-triazatricyclo[13.2.1.02,7]octadeca-1(17),2,4,6,15(18)-pentaen-5-yl]carbamate dihydrochloride [ No CAS ]
  • 16
  • [ 1260878-78-1 ]
  • [ 106356-53-0 ]
  • [ 1422510-45-9 ]
YieldReaction ConditionsOperation in experiment
85% Intermediate 23 A. (i?)-l-(4-Chloro-3-fiuoropyridin-2-yl)but-3-en-l-ol: A solution of 1 M allylbis((15',2i?,35',55)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane in pentane in anhydrous THF (10 mL) was cooled to -78 C. To the solution was added 4- chloro-3-fluoropicolinaldehyde (0.5 g, 3.13 mmol) in 10 mL of THF dropwise for 20 min. The resulting solution was stirred for additional 1 h. To the mixture was added MeOH (1 mL), followed addition of lithium hydroxide (0.300 g, 12.54 mmol), hydrogen peroxide (0.384 mL, 12.54 mmol) and 10 mL of 1 N NaOH. The content was allowed to warm up to rt and stirred for 1 h. The reaction mixture was diluted with EtOAc, washed with brine (2x20 mL), dried over Na2S04, concentrated and purified by silica gel chromatography to provide (i?)-l-(4-chloro-3-fluoropyridin-2-yl)but-3-en-l-ol (0.54 g, 85%). MS (ESI) m/z: 202.1 (M+H)+.
85% A solution of 1 M allylbis((1S,2R,3S,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)borane in pentane in anhydrous THF (10 mL) was cooled to -78 C. To the solution was added <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (0.5 g, 3.13 mmol) in 10 mL of THF dropwise for 20 min. The resulting solution was stirred for additional 1 h. To the mixture was added MeOH (1 mL), followed addition of lithium hydroxide (0.300 g, 12.54 mmol), hydrogen peroxide (0.384mL, 12.54 mmol) and 10 mL of 1 N NaOH. The reaction mixture was allowed to10 warm up to rt and stirred for 1 h. The reaction mixture was diluted with EtOAc, washed with brine (2x20 mL), driedover Na2S04, concentrated and purified by silica gel chromatography to provideintermediate 9A (0.54 g, 85%).
  • 17
  • [ 1260878-78-1 ]
  • [ 196929-78-9 ]
  • [ 1422510-26-6 ]
YieldReaction ConditionsOperation in experiment
100% With caesium carbonate; In dichloromethane; at 20℃; for 1h; Intermediate 15 A. (5',E)-N-((4-Chloro-3-fluoropyridin-2-yl)methylene)-2- methylpropane-2-sulfinamide: A solution of (i?)-2-methylpropane-2-sulfinamide (0.540 g, 4.32 mmol), <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (0.627 g, 3.93 mmol) and Cs2C03 (1.921 g, 5.89 mmol) in DCM (20 mL) was stirred for 1 h at rt. The reaction mixture was diluted with EtOAc and washed with brine (3x20 mL). The organic layer was dried over MgS04, filtered and concentrated in vacuo to provide the desired product (1.1 g, 100%). MS (ESI) m/z: 263.0 (M+H)+.
  • 18
  • [ 1260878-78-1 ]
  • methyl N-[(10R,14S)-14-[(3R)-3-[(tert-butyldimethylsilyl)oxy]-3-(4-chloro-3-fluoropyridin-2-yl)propyl]amino}-17-methoxy-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02'7]nonadeca-1(18),2,4,6,15(19),16-hexaen-5-yl]carbamate [ No CAS ]
  • 19
  • [ 1260878-78-1 ]
  • methyl N-[(10R,14S)-14-{N-[(3R)-3-[(tert-butyldimethylsilyl)oxy]-3-(4-chloro-3-fluoropyridin-2-yl)propyl]-2-(diethoxyphosphoryl)acetamido}-17-methoxy-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02'7]nonadeca-1(18),2,4,6,15(19),16-hexaen-5-yl]carbamate [ No CAS ]
  • 20
  • [ 1260878-78-1 ]
  • methyl N-[(10R,14S)-14-{N-[(3R)-3-(4-chloro-3-fluoropyridin-2-yl)-3-hydroxypropyl]-2-(diethoxyphosphoryl)acetamido}-17-methoxy-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02'7]nonadeca-1(18),2,4,6,15(19),16-hexaen-5-yl]carbamate [ No CAS ]
  • 21
  • [ 1260878-78-1 ]
  • methyl N-[(10R,14S)-14-{N-[3-(4-chloro-3-fluoropyridin-2-yl)-3-oxopropyl]-2-(diethoxyphosphoryl)acetamido}-17-methoxy-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02'7]nonadeca-1(18),2,4,6,15(19),16-hexaen-5-yl]carbamate [ No CAS ]
  • 22
  • [ 109-72-8 ]
  • [ 2546-56-7 ]
  • [ 1260878-78-1 ]
YieldReaction ConditionsOperation in experiment
Example 306 Synthesis of 4-chloro-3-fluoropicolinaldehyde. To a solution of 2, 2, 6, 6-tetramethylpiperidine (35.4 g, 250.88 mmol) in 200 mL THF was added n-Butyllithium (2.4 M in hexane, 100 mL, 240 mmol) dropwise at 0 C. The reaction mixture was cooled to -78 C. after stirring at 0 C. for lh and a solution of 4-chloro-3-fluoropyridine (30.0 g, 228.08 mmol) in THF (100 mL) was added dropwise. The resulting reaction mixture was stirred at -78 C. for 2 h, a solution of DMF (17.5 g, 239.48 mmol) in THF (50 mL) was added dropwise, and the resulting reaction mixture was stirred at -78 C. for another 1 h. The reaction was quenched with H2O (50 mL), and extracted with ethyl acetate (200 mL*3). The combined organic layers were washed with brine, dried over with anhydrous magnesium sulphate, filtered, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=3/1) to afford 4-chloro-3-fluoropicolinaldehyde (26.0 g, yield: 71%). ESI-MS [M+H]+: 160.1.
  • 23
  • [ 1260878-78-1 ]
  • (4-chloro-3-fluoropyridin-2-yl)methanamine hydrochloride [ No CAS ]
  • 24
  • [ 1260878-78-1 ]
  • N-((4-chloro-3-fluoropyridin-2-yl)methyl)formamide [ No CAS ]
  • 25
  • [ 1260878-78-1 ]
  • 7-chloroimidazo[1,5-a]pyridine [ No CAS ]
  • 26
  • [ 1260878-78-1 ]
  • [ 146374-27-8 ]
  • N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; caesium carbonate; Synthesis of N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide. To a solution of <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (26.0 g, mixtutre, 163.0 mmol) in DCM (100 mL) was added cesium carbonate (96.0 g, 293.3 mmol) and 2-methylpropane-2-sulfinamide (19.8 g, 163.0 mmol) at RT. The reaction mixture was stirred for 3 h at RT. After the reaction was complete, the reaction mixture was filtrated and washed with DCM three times. To the combined mixture was added MeOH (40 mL), and then the resulting mixture was cooled to 0 C. by ice-water bath. Sodium borohydride (15.5 g, 409.0 mmol) was added slowly in portions. The reaction mixture was warmed up to RT and stirred at this temperature for 2 h. The reaction was quenched with H2O carefully. The resulting mixture was extracted with DCM (100 mL*3), the combined organic solvent was dried by sodium sulfate, filtered, and concentrated to get crude N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide (43.3 g, crude) as yellow solid. ESI-MS [M+H]+: 265.1.
  • 27
  • [ 1260878-78-1 ]
  • (+)-(S)-N-((4-chloro-3-fluoropyridin-2-yl)methyl)-2-methylpropane-2-sulfinamide [ No CAS ]
  • 28
  • [ 1260878-78-1 ]
  • (S)-ethyl 2-(2-((4-(2-((1,1-dimethylethylsulfinamido)methyl)-3-fluoropyridin-4-yl)-1-(methylsulfonyl)-1H-indol-6-yl)methoxy)phenyl)acetate [ No CAS ]
  • 29
  • [ 1260878-78-1 ]
  • [ 343338-28-3 ]
  • (S)-N-((4-chloro-3-fluoropyridin-2-yl)methylene)-2-methylpropane-2-sulfinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In dichloromethane; at 20℃; for 1h; To a solution of <strong>[1260878-78-1]4-chloro-3-fluoropicolinaldehyde</strong> (220a) (6.73 g, 42.2 mmol; CASNo. 1260878-78-1) and Cs2C03 (27.5 g, 84 mmol) in DCM (350 mL) was added (S)-2- methylpropane-2-sulfmamide (5.88 g, 48.5 mmol) and stirred at rt for 1 h. The reaction mixture was diluted with DCM and washed with brine (3 x 200 mL). The organic layer was dried, filtered and concentrated in vacuo to afford (S)-N-((4-chloro-3 -fluoropyri din-2 - yl)methylene)-2-methylpropane-2-sulfmamide (220b) (11.08 g,l00 % yield) which was used in the next reaction without further purification; 'H NMR (300 MHz, DMSO-rL) d 8.59 (d, J = 5.1Hz, 1H), 8.56 (s, 1H), 7.97 (dd, J = 5.6, 5.0 Hz, 1H), 1.21 (s, 9H).
 

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