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[ CAS No. 1023813-80-0 ] {[proInfo.proName]}

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Chemical Structure| 1023813-80-0
Chemical Structure| 1023813-80-0
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Product Details of [ 1023813-80-0 ]

CAS No. :1023813-80-0 MDL No. :MFCD09881254
Formula : C8H9BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 213.07 Pubchem ID :-
Synonyms :

Safety of [ 1023813-80-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:
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Application In Synthesis of [ 1023813-80-0 ]

* 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 [ 1023813-80-0 ]

[ 1023813-80-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 129686-16-4 ]
  • [ 1023813-80-0 ]
YieldReaction ConditionsOperation in experiment
85% To a dry three-neck round bottom flask was added NaBH4 (190 mg, 50.00 mmol), followed by a solution of 6-bromo-3,4-dihydro-l,8-naphthyridin- 2(lH)-one (Ref: Seefeld, Mark A., et al. Journal of Medicinal Chemistry 2003, 46, 1627 - 1635) (227 mg, 10.00 mmol) in anhydrous THF (20 mL). Then a 47% solution of BF3 etherate (994 mg, 70 mmol) was added dropwise under nitrogen at 0 C, and the mixture was stirred at rt for 2 h, whereupon analysis by LC-MS indicated the presence of the desired product. The reaction was quenched by saturated aq NH4C1 (5 mL) carefully. The mixture was extracted with EtOAc (3 x 50mL). The combined organic layers were dried over MgS04, concentrated under reduced pressure to give 6-bromo-l,2,3,4-tetrahydro-l,8-naphthyridine (180 mg. 85% yield). LC-MS (ESI) m/z 212, 214 (M + H)+.
9.3 g With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 16h; To a cooled (0 C.) solution of <strong>[129686-16-4]6-bromo-3,4-dihydro-1H-[1,8]naphthyridin-2-one</strong> (10.0 g, 44.0 mmol) in THF (500 mL) is added sodium borohydride (8.3 g, 220 mmol) followed by boron trifluoride diethyl ether complex (38.7 mL, 308 mmol), dropwise. The resulting mixture is allowed to warm and stir at room temperature for 16 h. The reaction is carefully quenched with the dropwise addition of 1N HCl (15 mL). Once quenched, additional 1N HCl (85 mL) is added and the mixture is stirred at room temperature for 16 h. The mixture is concentrated, diluted with water and made basic (pH 8) with the addition of powdered sodium bicarbonate. The mixture is extracted with EtOAc and the combined organic layers are washed with brine, dried (Na2SO4) and concentrated to obtain the title compound (9.3 g).
With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere; To a mixture of NaBH4 (950 mg, 25.0 mmol) and a solution of 6-bromo-3,4- dihydro-l,8-naphthyridin-2(lH)-one (1.135 g, 5.0 mmol) in anhydrous THF (100 mL) was added a solution of BF3-Et20 (9.5 mL, 35.0 mmol, 47%) dropwise at 0 C under nitrogen atmosphere. The mixture was stirred at rt for 2 hours, quenched with saturated NH4C1 aqueous solution (25 mL), and the resulted mixture was extracted with DCM/MeOH (10/1, 50 mL x 3). The combined organic layers were dried over anhydrous Na2S04, and concentrated in vacuo to give the title compound as a white solid (2.8 g. >100%). The crude product was used directly in the next step without further purification. MS (ESI, pos. ion) m/z: 213.0 (M+l); 1H NMR (400 MHz, DMSO-de): delta 1.70-1.87 (m, 2H), 2.76 (t, J = 6.1 Hz , 2H), 3.38 (t, J = 5.6 Hz, 2H), 7.84 (d, J= 0.9 Hz, 1H), 8.03 (d, J= 2.0 Hz, 1H), 8.18 (br, 1H).
9.3 g With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 16h; To a cooled (0 C) solution 6-bromo-3,4-dihydro-lH-[l,8]naphthyridin-2-one (10 g, 44 mmol) in THF (500 mL) is added sodium borohydride (8.3 g, 220 mmol) followed by boron trifluoride diethyl ether complex (39 mL, 310 mmol) dropwise. The resulting mixture is allowed to warm to room temperature and it is stirred for 16 hr. The reaction is carefully quenched with the dropwise addtion of 1.0 N HC1 aquous solution (15 mL). Once quenched, additional 1.0 N HC1 aqueous solution (85 mL) is added and the mixture is stirred at room temperature for 16 hr. The mixture is then concentrated, diluted with water and made basic (pH 8) with the addition of powdered sodium bicarbonate. The mixture is extracted with EtOAc and the combined organic layers are washed with brine, dried over Na2S04 and concentrated to give 9.3 g of 6-bromo- 1,2,3,4- tetrahydro- [ 1,8] naphthyridine .
With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 20℃; for 2h;Inert atmosphere; The compound NaBH4 (950 Mg, 25.0 mmol), 6 - bromo - 3, 4 - dihydro - 1, 8 - naphthyridine -2 (1 H) - one (1.135 g, 5.0 mmol) and anhydrous THF (100 ml) mixture is cooled to 0 C, then under the protection of nitrogen, added dropwise to the reaction solution in the BF3 ·Et2 O (9.5 ml, 35.0 mmol, 47%), room temperature stirring for 2 hours, add saturated NH4 Cl aqueous solution (25 ml) quenching the reaction, DCM/MeOH mixture (10/1, 50 ml x 3) extraction, the combined organic phase with anhydrous Na2 SO4 Drying, concentrated under reduced pressure, to obtain the title compound as a white solid (2.8 g,>100%). The crude product without further purification, is directly used for the next step of the reaction.
With sodium tetrahydroborate; boron trifluoride diethyl etherate; In tetrahydrofuran; at 0 - 20℃; for 16h; To a solution of <strong>[129686-16-4]6-bromo-3,4-dihydro-1,8-naphthyridin-2(1H)-one</strong> (5.0 g, 21.80 mmol) and NaBH4 (4.18 g, 110.49 mmol) in THF (140 mL) was added BF3-Et20 (20 mL, 157.83 mmol) dropwise at 0 C. The reaction mixture was stirred for 16 h at room temperature. iN HC1 solution (100 mL) was added and the reaction mixture was stirred for an additional 16 h at room temperature. The pH value of the mixture was then adjusted to 8 with aq. sat. NaHCO3 solution. The resulting mixture was extracted with ethyl acetate (3 x 150 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to give 6-bromo-1,2,3,4-tetrahydro-1,8-naphthyridine as a white solid. MS: (ESI, m/z): 213, 215 [M+H]t

  • 2
  • [ 1023813-80-0 ]
  • [ 676515-34-7 ]
  • 3
  • [ 23612-57-9 ]
  • [ 1023813-80-0 ]
  • 4
  • [ 6457-49-4 ]
  • [ 55276-43-2 ]
  • [ 1023813-80-0 ]
  • [ 79-04-9 ]
  • [ 162012-70-6 ]
  • N-[4-(6-bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-1-yl)-7-[(piperidin-4-yl)methoxy]quinazolin-6-yl]-2-(4-methanesulfonylpiperazin-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
48.6% Intermediate IV andReaction of 6-bromo-2,3,4-dihydro- (1,8) naphthyridine to give Va,Reaction with piperidin-4-yl-methanol,A dark yellow solid VIa was obtained.The intermediate VIa with activated carbon,Reduction of ferric chloride and hydrazine hydrate gives the off-white solid VIIa.Then VIIa and chloroacetyl chloride condensation,Compound VIIIa is obtained,In the condensation with 1-methylsulfonyl-piperazine,The target compound was obtained. Yield: 48.6%.
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