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Chemical Structure| 1261487-70-0 Chemical Structure| 1261487-70-0

Structure of 1261487-70-0

Chemical Structure| 1261487-70-0

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Product Details of [ 1261487-70-0 ]

CAS No. :1261487-70-0
Formula : C9H6BrNO
M.W : 224.05
SMILES Code : OC1=CC2=CC=C(Br)C=C2N=C1
MDL No. :MFCD18413586
InChI Key :QSSKHPOBNVWRPS-UHFFFAOYSA-N
Pubchem ID :65711196

Safety of [ 1261487-70-0 ]

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

Application In Synthesis of [ 1261487-70-0 ]

* 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 [ 1261487-70-0 ]

[ 1261487-70-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 1429790-77-1 ]
  • [ 1261487-70-0 ]
  • (+)-4-cyclopropyl-9-[2,6-difluoro-4-(3-hydroxy-7-quinolinyl)phenyl]methyl}-1-oxa-4,9-diazaspiro[5.5]undecane-3,8-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; at 130.0℃; for 0.416667h;Microwave irradiation; General procedure: A 5 mL microwave vial equipped with a stirbar was charged with 7-bromo-3-chloroquinoline (152 mg, 0.629 mmol) and PdCI2(dppf)-CH2CI2 adduct (29.9 mg, 0.037 mmol). The solids were taken up in 1 ,4-dioxane (0.546 mL) and treated with a 0.338M 1 ,4-dioxane solution of 4-cyclopropyl-9-(2,6-difluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecane-3,8-dione (1.55 mL, 0.524 mmol). The mixture was treated with 2M aq potassium carbonate (0.524 mL, 1.048mmol). The vial was sealed and the mixture subjected to microwave irradiation at130 Cfor2S mm on very high absorption setting (Biotage Initiator 60). The mixture was then cooled to room temperature and partitioned between 15 mL each of chloroform and saturated aq sodium bicarbonate. The mixture was separated, the organic layer isolated, and the aqueous layer re-extracted with an additional 15 mL chloroform. The organicswere then pooled, dried over sodium sulfate, filtered, and concentrated to a residue. The residue was purified by flash chromatography (0.3-5.5% methanol:dichloromethane). Fractions containing the desired material were pooled and concentrated to a residue which was then resolved by chiral HPLC (Chiralpak AS-H, 95:5 acetonitrile:methanol) to afford title compound in 100% ee as a white solid (58 mg, 0.112 mmol, 21% yield). Following the procedure described in Example 7c with <strong>[1261487-70-0]7-bromo-3-quinolinol</strong> afforded the title product in 100% ee (24% yield) using chiral HPLC (Chromegachiral CC4, 50 :50 ethanol:heptane). MS(ES) me 494.2 [M+H]. cLD = +11 deg (c = 0.4,dichloromethane).
  • 2
  • [ 1246548-95-7 ]
  • [ 1261487-70-0 ]
YieldReaction ConditionsOperation in experiment
48% With hydrogen bromide; acetic acid; at 120.0℃; for 96.0h; A solution of 7-bromo-3-methoxyquinoline (1.1 g, 4.62 mmol) in acetic acid (20mL) was treated with 48% hydrobromic acid (5.0 mL, 92 mmol) and heated under reflux at 120 C for 4 days. Analysis by LCMS then showed the reaction had progressed to approximately 50% completion. The mixture was poured onto ice and adjusted to a basic pH with ammonium hydroxide solution. The aqueous mixture was extracted with diethyl ether (3x), the combined extracts were evaporated, and the residue was purifiedby flash chromatography (10-50% ethyl acetate/hexanes) to give the title product (500 mg, 2.232 mmol, 48% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.55 (d, J=2.53 Hz, 1H), 7.63 (dd, J=8.59, 2.02 Hz, 1H), 7.80 (d, J=8.84 Hz, 1H), 8.10 (d, J=1.77 Hz, 1H), 8.60 (d, J=2.78 Hz, 1H), 10.51 (s, 1H).
48% With hydrogen bromide; In acetic acid; at 120.0℃; for 96.0h;Reflux; A solution of 7-bromo-3-methoxyquinoline (1.1 g, 4.62 mmol) in acetic acid (20 mL) was treated with 48% hydrobromic acid (5.0 mL, 92 mmol) and heated under reflux at 120 C for 4 days. LCMS then showed the reaction had progressed about 50%>. The mixture was poured onto ice and basified with ammonium hydroxide solution. The aqueous mixture was extracted with diethyl ether (x3) and the combined extracts were evaporated under reduced pressure. Purification by flash chromatography (10-50% ethyl acetate in hexanes) provided the title compound (500 mg, 48 %) as a tan solid. 1H NMR (400 MHz, DMSO- 6) delta ppm 7.55 (d, J=2.53 Hz, 1 H) 7.63 (dd, J=8.59, 2.02 Hz, 1 H) 7.80 (d, J=8.84 Hz, 1 H) 8.10 (d, J=1.77 Hz, 1 H) 8.60 (d, J=2.78 Hz, 1 H) 10.51 (s, 1 H)
  • 3
  • [ 1261487-70-0 ]
  • [ 1534373-21-1 ]
  • [ 1534371-20-4 ]
YieldReaction ConditionsOperation in experiment
20 mg With potassium carbonate; In 1,4-dioxane; water; at 100.0℃; for 1.0h;Sealed tube; Inert atmosphere; Microwave irradiation; a) In a sealed microwave vial purged with nitrogen, a mixture of 9-[(4-bromo-2,6- difluorophenyl)methyl]-4-cyclopropyl- 1 -oxa-4,9-diazaspiro[5.5]undecan-3-one (100 mg, 0.231 mmol), bis(pinacolato)diboron (65 mg, 0.256 mmol), potassium acetate (68 mg, 0.693 mmol) and l, -bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (10 mg, 0.012 mmol) in 1,4-dioxane (5 mL) was stirred at 100 C for 1 h. The reaction was cooled to room temperature to give the intermediate 4-cyclopropyl-9-(2,6- difluoro-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzyl)-l-oxa-4,9- diazaspiro[5.5]undecan-3-one . To the reaction mixture was added <strong>[1261487-70-0]7-bromoquinolin-3-ol</strong> (51.8 mg, 0.231 mmol) and 2M aqueous potassium carbonate (1 mL, 2 mmol). The reaction was stirred at 100 C for 1 h and then cooled to room temperature. The reaction mixture was diluted with ethyl acetate (30 mL) and water (10 mL), and the layers were separated. The aqueous layer was extracted with ethyl acetate (20 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Purification by silica gel chromatography (0-5% methanol/ethyl acetate) followed by purification by reverse phase HPLC (10-90% acetonitrile /water + 0.1% NH4OH) provided the title product as a white solid (20 mg, 18%). MS(ES)+ m/e 480.1 [M+H]+.
  • 4
  • [ 1261487-70-0 ]
  • 7-bromo-4-iodoquinolin-3-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With iodine; potassium iodide; sodium hydroxide; In water; at 25.0℃; for 883.0h; Into a 250-mL round-bottom flask, was placed a solution of <strong>[1261487-70-0]7-bromoquinolin-3-ol</strong> (2000 mg, 8.93 mmol, 1.00 equiv) in 2 N NaOH solution (40 mL). To this mixture, a solution of iodine (4536 mg, 17.86 mmol) in 20% aqueous potassium iodide (40 mL) was added dropwise. The resulting solution was stirred for 3 h at 25C. Then the pH value of the solution was adjusted to 6-7 with acetic acid. The solids were collected by filtration and washed with 15 mL of H2O three times. This provided 2740 mg (88%) of 7-bromo-4- iodoquinolin-3-ol as a yellow solid. LC-MS: (ES, m/z): [M+H]+ = 350.0.
  • 5
  • [ 1261487-70-0 ]
  • 3-[7-bromofuro[2,3-c]quinolin-2-yl]propan-1-ol [ No CAS ]
  • 6
  • [ 1261487-70-0 ]
  • 7-bromo-2-(3-hydroxypropyl)furo[2,3-c]quinolin-5-ium-5-olate [ No CAS ]
  • 7
  • [ 1261487-70-0 ]
  • 3-[4-amino-7-bromofuro[2,3-c]quinolin-2-yl]propan-1-ol [ No CAS ]
  • 8
  • [ 1261487-70-0 ]
  • 3-[4-amino-7-(1H-pyrazol-3-yl)furo[2,3-c]quinolin-2-yl]propan-1-ol [ No CAS ]
 

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