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[ CAS No. 1337882-50-4 ] {[proInfo.proName]}

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Chemical Structure| 1337882-50-4
Chemical Structure| 1337882-50-4
Structure of 1337882-50-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1337882-50-4 ]

CAS No. :1337882-50-4 MDL No. :MFCD22380361
Formula : C16H12BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 314.18 Pubchem ID :-
Synonyms :

Safety of [ 1337882-50-4 ]

Signal Word:Warning Class:
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:
Hazard Statements:H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1337882-50-4 ]

* 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 [ 1337882-50-4 ]

[ 1337882-50-4 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 13669-57-3 ]
  • [ 100-39-0 ]
  • [ 1337882-50-4 ]
YieldReaction ConditionsOperation in experiment
89% With potassium carbonate; In acetone; at 20℃; A solution of J.iii (760 mg, 3.39 mmol), benzyl bromide (0.44 mL, 3.73 mmol) and K2C03 (563 mg, 4.07 mmol) in acetone (20 mL) was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by chromatography (eluting with 20% EtOAc in haxane) to give the title compound as white solid (970 mg, yield 89%). H-NMR (400 MHz, DMSO-d6) delta ppm 8.76 (d, 1 H), 8.23 (d, 1 H), 8.05 (d, 1 H), 7.49-7.34 (m, 6H), 7.08 (d, 1 H), 5.20 (s, 2H). LCMS (method B): [M+H]+ = 314, tR = 2.91 min.
89% With potassium carbonate; In acetone; at 20℃; A solution of B.i (760 mg, 3.39 mmol), benzyl bromide (0.44 ml_, 3.73 mmol) and K2C03 (563 mg, 4.07 mmol) in acetone (20 ml.) was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by chromatography (eluting with 20% EtOAc in haxane) to give the title compound as white solid (970 mg, yield 89%). LCMS (method N): [M+H]+ = 314, tR = 2.91 min. 1 H-NMR (400 MHz, DMSO-d6) delta ppm 8.76 (d, 1 H), 8.23 (d, 1 H), 8.05 (d, 1 H), 7.49-7.34 (m, 6H), 7.08 (d, 1 H), 5.20 (s, 2H).
89% With potassium carbonate; In acetone; at 20℃; A solution of B.i (760 mg, 3.39 mmol), benzyl bromide (0.44 mL, 3.73 mmol) and K2CO3 (563 mg, 4.07 mmol) in acetone (20 mL) was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by chromatography (eluting with 20% EtOAc in haxane) to give the title compound as white solid (970 mg, yield 89%). LCMS (method N): [M+H]+=314, tR=2.91 min. 1H-NMR (400 MHz, DMSO-d6) delta ppm 8.76 (d, 1H), 8.23 (d, 1H), 8.05 (d, 1H), 7.49-7.34 (m, 6H), 7.08 (d, 1H), 5.20 (s, 2H).
89% With potassium carbonate; In acetone; at 20℃; A solution of J.iii (760 mg, 3.39 mmol), benzyl bromide (0.44 mL, 3.73 mmol) and K2CO3 (563 mg, 4.07 mmol) in acetone (20 mL) was stirred at rt overnight. The reaction mixture was concentrated under reduced pressure. The crude product was purified by chromatography (eluting with 20% EtOAc in haxane) to give the title compound as white solid (970 mg, yield 89%). 1H-NMR (400 MHz, DMSO-d6) delta ppm 8.76 (d, 1H), 8.23 (d, 1H), 8.05 (d, 1H), 7.497.34 (m, 6H), 7.08 (d, 1H), 5.20 (s, 2H). LCMS (method B): [M+H]+=314, tR=2.91 min.
68% With potassium carbonate; In acetonitrile; at 80℃; for 3h;Inert atmosphere; 3-Bromo-6-hydroxyquinoline (760 mg, 3.39 mmol)Potassium carbonate (563 mg, 4.07 mmol)Placed in a 100 mL round bottom flask, 15 ml of acetonitrile was added,Benzyl bromide (0.44 mL) was added with stirring,The mixture was then heated to 80 C for 3 hours,After the reaction, the reaction solvent was removed,The crude product was purified by column chromatography to give 3-bromo-6-benzyloxyquinoline (760 mg, yield 68%).

  • 2
  • [ 1337882-50-4 ]
  • [ 727650-61-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium <i>tert</i>-butylate; tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene / toluene / 8.16 h / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; potassium <i>tert</i>-butylate / toluene / 8 h / 100 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 60 °C / 760.05 Torr
  • 3
  • [ 1015484-22-6 ]
  • [ 1337882-50-4 ]
  • [ 1427473-83-3 ]
YieldReaction ConditionsOperation in experiment
33% With di-μ-bromobis(tri-tert-butylphosphino)dipalladium(I); caesium carbonate In tetrahydrofuran; water at 80℃; Inert atmosphere; 1-((6-(benzyloxy)naphthalen-2-yl)methyl)-4-methylpiperazine (Q4.i) A mixture of Intermediate B (500 mg, 1.60 mmol), potassium trifluoro[(4- methylpiperazin-1 -yl)methyl]borate (351 mg, 1.60 mmol), dibromobis(tri-tert- butylphosphine)dipalladium(l) (124 mg, 0.16 mmol), and caesium carbonate (1.56 g, 4.79 mmol) in THF (5 mL)/H20 (0.5 ml.) was bubbled with argon for 20 min. The result mixture was kept at 80°C and stirred overnight. Then the reaction mixture was cooled to rt, water was added and the product was then extracted with DCM three times. The combined organic phase was dried over anhydrous Na2S04, filtered and concentrated. The crude product was purified by chromatography (eluting with 5% MeOH in DCM) to give the title compound as yellow solid (180 mg, yield 33%). 1 H-NMR (400 MHz, CDCl3) δ ppm 8.74 (s, 1 H), 8.00 (d, 1 H), 7.93 (s, 1 H), 7.49-7.35(m, 5H), 7.13 (s, 1 H), 5.19 (s, 2H), 3.67 (s, 2H), 3.49 (s, 1 H), 2.75-2.40 (broad, 7H), 2.32 (s, 3H).
  • 4
  • [ 4318-37-0 ]
  • [ 1337882-50-4 ]
  • [ 1427473-97-9 ]
YieldReaction ConditionsOperation in experiment
58% With tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene; potassium tert-butylate; In toluene; at 110℃; for 3.25h;Inert atmosphere; A mixture of Pd2(dba)3 (72.9 mg, 0.080 mmol), xantphos (101 mg, 0.175 mmol), intermediate B (500 mg, 1 .591 mmol), 1-methyl-1 ,4-diazepane (1.1 ) (182 mg, 1 .591 mmol) and KOtBu (357 mg, 3.18 mmol) in toluene (10 ml) was bubbling with nitrogen for 15 min. The reaction was stirred at 1 10C for 3 hr under nitrogen atmosphere. The reaction mixture was filtered and concentrated. The crude product was purified by chromatography to give the title compound (320 mg, yield 58%). LCMS (method N): [M+H]+ = 348, tR = 1.75 min.
58% With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 110℃; for 3h;Inert atmosphere; A mixture of Pd2(dba)3 (72.9 mg, 0.080 mmol), xantphos (101 mg, 0.175 mmol), intermediate B (500 mg, 1.591 mmol), 1-methyl-1,4-diazepane (1.1) (182 mg, 1.591 mmol) and KOtBu (357 mg, 3.18 mmol) in toluene (10 ml) was bubbling with nitrogen for 15 min. The reaction was stirred at 110 C. for 3 hr under nitrogen atmosphere. The reaction mixture was filtered and concentrated. The crude product was purified by chromatography to give the title compound (320 mg, yield 58%). LCMS (method N): [M+H]+=348, tR=1.75 min.
  • 5
  • [ 42185-06-8 ]
  • [ 1337882-50-4 ]
  • [ 1427474-57-4 ]
YieldReaction ConditionsOperation in experiment
60.9% With tris-(dibenzylideneacetone)dipalladium(0); 4a,9a-dihydro-9,9-dimethyl-4,5-bis(diphenylphosphino)-xanthene; potassium tert-butylate; In toluene; at 100℃; for 8.16h;Inert atmosphere; A mixture of Intermediate B (1.0 g, 3.18 mmol), <strong>[42185-06-8]3-methylmorpholine</strong> (0.966 g,9.55 mmol), Pd2(dba)3 (0.291 g, 0.318 mmol), xantphos (0.368 g, 0.637 mmol) and KO'Bu (0.714 g, 6.37 mmol) in toluene (30 ml) wasbubbled with argon for 10 min. The reaction was stirred at 100C for 8 h, cooled and concentrated under reduced pressure. The residue was dissolved in 50 ml of EtOAc, washed with water and brine. The organic phase was dried over Na2S04, filtered and concentrated. The residue was purified by silica gel chromatography (DCM/MeOH = 30/1 ) to afford the title compound as pale yellow solid (800 mg, 60.9% yield). LCMS (method B): [M+H]+ = 335, tR = 2.53 min.
60.9% With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 100℃; for 8h;Inert atmosphere; A mixture of Intermediate B (1.0 g, 3.18 mmol), <strong>[42185-06-8]3-methylmorpholine</strong> (0.966 g, 9.55 mmol), Pd2(dba)3 (0.291 g, 0.318 mmol), xantphos (0.368 g, 0.637 mmol) and KOtBu (0.714 g, 6.37 mmol) in toluene (30 ml) was bubbled with argon for 10 min. The reaction was stirred at 100 C. for 8 h, cooled and concentrated under reduced pressure. The residue was dissolved in 50 ml of EtOAc, washed with water and brine. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (DCM/MeOH=30/1) to afford the title compound as pale yellow solid (800 mg, 60.9% yield). LCMS (method B): [M+H]+=335, tR=2.53 min.
  • 6
  • [ 52898-32-5 ]
  • [ 1337882-50-4 ]
  • C28H22N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 120℃; Inert atmosphere; General procedure: To a solution of 6-substituted or 7-substituted 3-bromoquinoline (17-23, 1.0 mmol), N-(but-3-enyl)phthalimide (0.22 g, 1.1 mmol), NaOAc (0.14 g, 2.0 mmol) and PPh3 (31 mg, 0.12 mmol) in 4 mL of DMF was added Pd(OAc)2 (9 mg, 0.04 mmol) at room temperature under Ar condition. The mixture was heated to 120 °C and stirred at 120 °C overnight. The reaction solution was allowed to cool to room temperature and diluted with 100 mL of DCM, washed with brine (6×100 mL), dried with Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE: EA = 4: 1) to give 24-30, as a white solid.
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