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[ CAS No. 409346-71-0 ]

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2D
Chemical Structure| 409346-71-0
Chemical Structure| 409346-71-0
Structure of 409346-71-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 409346-71-0 ]

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SDS

Product Details of [ 409346-71-0 ]

CAS No. :409346-71-0MDL No. :MFCD09029947
Formula : C12H12BrNO Boiling Point : -
Linear Structure Formula :-InChI Key :N/A
M.W :266.13Pubchem ID :11173142
Synonyms :

Computed Properties of [ 409346-71-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 409346-71-0 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 409346-71-0 ]

  • Downstream synthetic route of [ 409346-71-0 ]

[ 409346-71-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 409346-71-0 ]
  • [ 409346-72-1 ]
  • 3-ethyl-2-methoxyquinolin-6-yl trans-4-methoxycyclohexyl ketone [ No CAS ]
  • [ 409340-66-5 ]
  • 2
  • [ 409346-71-0 ]
  • [ 351464-84-1 ]
  • [ 409341-34-0 ]
  • 3
  • [ 124-41-4 ]
  • [ 409346-70-9 ]
  • [ 409346-71-0 ]
  • 4
  • [ 409346-71-0 ]
  • [ 97-96-1 ]
  • C18H25NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example A4 Preparation of intermediate 8 nBuLi 1.6M in hexane (0. 129 mol) was added dropwise at-60C under N2 flow to a mixture of <strong>[409346-71-0]6-bromo-3-ethyl-2-methoxy-quinoline</strong> (0.0996 mol) in THF (265ml). The mixture was stirred at-60C for 1 hour. A mixture of 2-ethyl-butanal (0.119 mol) in THE (100ml) was added dropwise at-60C. The mixture was stirred at-60C for 2 hours, then at-40C for 1 hour, poured out into a saturated ammonium chloride solution and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered and the solvent was evaporated. The product was used without further purification, yielding 28.62g of intermediate 8.
  • 5
  • [ 409346-71-0 ]
  • [ 29668-44-8 ]
  • C21H21NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example A; 2a.).Prepaj:ation.of interrnediate.6; nBuLi 1.6M in hexane (0.0382 mol) was added dropwise at -60C under N2 flow to amixture of 6-bromo-3-ethyl-2-methoxy- quinoline (0.03 mol) in THF (50ml). Themixture was stirred at -60C for 1 hour. A solution of 2,3-dihydro-l,4-benzodioxin-6-carboxaldehyde (0.0361 mol) in TBDF (50ml) was added dropwise. The mixture was20 stirred at -60C for 2 hours, then at -40C for 1 hour, poured out into water andammonium hydroxide and extracted with DCM. The organic layer was separated, dried(MgSO4), filtered and the solvent was evaporated. The product was used withoutfurther purification, yielding 10.56g of intermediate 6.
  • 6
  • [ 409346-71-0 ]
  • 1-(4-(2,3-dihydrobenzo[b][1,4]dioxine-6-carbonyl)piperidin-1-yl)ethanone [ No CAS ]
  • C28H32N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
b). Preparation of intermediate 36; ]^0OH5 nBuLi 1.6M in hexane (0.09 mol) was added slowly at -78C under N2 flow to asolution of 6-bromo-3-ethyl-2-methoxy- quinoline (0.075 mol) in THF (200ml). Themixture was stirred for 1 hour. A mixture of intermediate 35 (0.075 mol) in THF(100ml) was added dropwise at -78C. The mixture was stirred at -30C for 2 hours,poured out into water and ammonium chloride and extracted with EtOAc. The organic10 layer was separated, dried (MgSCU), filtered and the solvent was evaporated tilldryness. The residue (37.Ig) was purified by column chromatography over silica gel(15-35 /im) (eluent: DCM/MeOH/NEUOH 97/3/0.15). The desired fractions werecollected and the solvent was evaporated. The residue was crystallized from DIPE. Theprecipitate was filtered off and dried, yielding 0.8g of intermediate 36, melting point15 114C.; Examle A22; 0 ' 5 nBuLi 1.6M in hexane (0.09 mol) was added slowly at -78C under N2 flow to asolution of 6-bromo-3-ethyl-2-methoxy- quinoline (0.075 mol) in THF (200ml). Themixture was stirred for 1 hour. A mixture of l-acetyl-4-[(2,3-dihydro-l,4-benzodioxin-6-yl)carbonyl]- piperidine (0.075 mol) in THF (100ml) was added dropwise at -78C.The mixture was stirred at -30C for 2 hours, poured out into water and ammonium10 chloride and extracted with EtOAc. The organic layer was separated, dried (MgSCU),filtered and the solvent was evaporated till dryness. The residue (37.Ig) was purified bycolumn chromatography over silica gel (15-35 /) (eluent: DCMMeOH/NHtOH97/3/0.15). The desired fractions were collected and the solvent was evaporated. Theresidue was crystallized from PIPE. The precipitate was filtered off and dried, yielding15 0.8g of intermediate 70, melting point 114C.
  • 7
  • [ 409346-71-0 ]
  • [ 132391-55-0 ]
  • [ 854534-65-9 ]
YieldReaction ConditionsOperation in experiment
63% Example A15; a).Preparation.of intermediate.39; nBuLi 1.6M (0.02986 mol) was added at -78C under N2 flow to a solution of 6-bromo-3-ethyl-2-methoxy- quinoline (0.02488 mol) in THF (120ml). The mixture was10 stirred at -30C for 1 hour and cooled again to -70C. A mixture of l-(2,3-dihydro-l,4-benzodioxin-6-yl)-3-(l-piperidinyl)- 1-propanone (0.02488 mol) in THF (60ml) wasadded slowly. The mixture was stirred at -70C for 1 hour, poured out into water andammonium chloride and extracted with EtOAc. The organic layer was separated, dried(MgSO4), filtered and the solvent was evaporated till dryness. The residue (14.92g) was15 purified by column chromatography over silica gel (15-35 jum) (eluent:DCM/MeOH/NBUOH 94/6/0.1). The desired fractions were collected and the solventwas evaporated, yielding 7.2g (63%) of intermediate 39.; Example A21; Preparation of jntemediate.69; nBuLi 1.6M (0.02986 mol) was added at -78C under N2 flow to a solution of 6-20 bromo-3-ethyl-2-methoxy- quinoline (0.02488 mol) in THF (120ml). The mixture wasstirred at-30C for 1 hour and cooled again to -70C. A mixture of l-(2,3-dihydro-l,4-benzodioxin-6-yl)-3-(l-piperidinyl)- 1-propanone (0.02488 mol) in THF (60ml) wasadded slowly. The mixture was stirred at -70C for 1 hour, poured out into water andammonium chloride and extracted with EtOAc. The organic layer was separated, dried25 (MgSO4), filtered and the solvent was evaporated till dryness. The residue (14.92g) waspurified by column chromatography over silica gel (15-35 /) (eluent: DCM/MeOHTNHiOH 94/6/0.1). The desired fractions were collected and the solventwas evaporated, yielding: 7.2g (63%) of intermediate 69
  • 8
  • [ 409346-71-0 ]
  • [ 120-57-0 ]
  • C20H19NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example A12; Preparation of intermediate 32; nBuLi 1.6M (0.0451 mol) was added slowly at -78C under N2 flow to a solution of 6-bromo-3-ethyl-2-methoxy- quinoline (0.0376 mol) in THF (200ml). The mixture wasstirred for 90 min and cooled again to -78C. A mixture of piperonylaldehyde (0.037620 mol) in THF (100ml) was added dropwise. The mixture was stirred for 2 hours, pouredout into water and ammonium chloride and extracted with EtOAc. The organic layerwas separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. Theresidue (14.9g) was purified by column chromatography over silica gel (15-35 /im)(eluent: DCM/MeOH 99/1). The pure fractions were collected and the solvent was25 evaporated. The residue was crystallized from diethyl ether. The precipitate was filteredoff and dried, yielding Ig of intermediate 32, melting point 116C.
  • 9
  • [ 409346-71-0 ]
  • [ 451-40-1 ]
  • C26H23NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; XPhos;palladium diacetate; In xylene; at 145℃; for 20h; A mixture of deoxybenzoin (1 mmol), (1 mmol), XPHOS (0.08 mmol), palladium diacetate (0.04 mmol), cesium carbonate (2 mmol) in xylene (4 ml) was flushed with N2 and heated at 145C for 20 hours. The reaction was cooled to room temperature and 2 ml OfH2O and 10 ml OfCH2Cl2 were added. The layers were separated (Extralute) and the separated organic layer was concentrated in vacuo. The residue was purified by HPLC on RP with NH4HCO3 -buffer. The product fractions were collected and the solvent was evaporated. Yield : intermediate 13.
  • 10
  • [ 106-40-1 ]
  • [ 409346-71-0 ]
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