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Chemistry
Heterocyclic Building Blocks
Isoquinolines
7-Bromo-6-fluoroisoquinolin-1(2H)-one
Chemistry
Heterocyclic Building Blocks
Organic Building Blocks
Isoquinolines
Bromides Fluorinated Building Blocks Amides

[ CAS No. 923022-43-9 ]

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Product Details of [ 923022-43-9 ]

CAS No. :923022-43-9 MDL No. :MFCD27933028
Formula : C9H5BrFNO Boiling Point : -
Linear Structure Formula :- InChI Key :QLALLSRWJRAJOS-UHFFFAOYSA-N
M.W :242.05 Pubchem ID :59818253
Synonyms :

Safety of [ 923022-43-9 ]

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-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 923022-43-9 ]

* 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 [ 923022-43-9 ]

[ 923022-43-9 ] Synthesis Path-Downstream   1~3

  • 1
  • C9H5BrFN3O [ No CAS ]
  • [ 923022-43-9 ]
YieldReaction ConditionsOperation in experiment
In diphenylether at 230 - 250℃; for 0.5h; c To a solution of 4.0 g (16.3 mmol) of 3-(4-bromo-3-fluoro-phenyl)-acrylic acid in 60 mL acetone were subsequently added at 0 - 5°C 2.0 g (19.6 mmol) triethylamine in 10 mL of acetone followed by 2.3 g (21.2 mmol) of ethyl chloroformate in 10 mL of acetone. After stirring for 1 h at 0 - 5°C a solution of 1.6 g (24.5 mmol) of sodium azide in 9 mL of water was added. After stirring for 1 additional h the reaction mixture was poured onto 200 mL ice water and extraced with chloroform twice. The organic phase was dried over magnesium sulfate, 24 mL of diphenylether were added and the chloroform was cautiously removed in vacuo. The residue was then added dropwise into 60 mL of diphenylether, which had been preheated to 2500C. After complete addition the reaction mixture was stirred for additional 30 minutes at 230 - 2500C. After cooling EPO down to 1000C the reaction mixture was poured into 100 ml_ of heptane and after further cooling in an ice bath the precipitated product was filtered by suction and 2.4 g of crude 7-bromo-6-fluoro-2H-isoquinolin-1-one were obtained.
Reference： [1]Current Patent Assignee: SANOFI - WO2007/12421, 2007, A1 Location in patent: Page/Page column 44-45
  • 2
  • [ 923022-42-8 ]
  • [ 923022-43-9 ]
YieldReaction ConditionsOperation in experiment
83% With ammonium acetate; acetic acid at 100℃; for 3h; 12.9 g (49.5 mmol) 7-bromo-1-chloro-6-fluoro-isoquinoline (311) were dissolved in 250 ml_ of acetic acid. After adding 38.7 g (0.5 mol) ammonium acetate, the solution was stirred at 100 0C. After 3 h, the solvent was removed i. vac. and the residue was poured on water. The precipitate was filtered and dried to yield 9.91 g (83%) of the title compound. R1 = 1.15 min (Method C). Detected mass: 242.2/244.1 (M+H+).
83% With ammonium acetate; acetic acid at 100℃; for 3h; 12.9 g (49.5 mmol) 7-bromo-1-chloro-6-fluoro-isoquinoline (94) were dissolved in 250 ml of acetic acid. After addition of 38.7 g (0.5 mol) of ammonium acetate, the solution is stirred at 100 0C. After 3 h, the solvent was removed under reduced pressure and the residue was poured into water. The precipitate is filtered and dried to yield 9.91 g (83%) of the title compound. Rt = 1.15 min (Method C). Detected mass: 242.2/244.1 (M+H+).
Reference： [1]Current Patent Assignee: SANOFI - WO2007/12421, 2007, A1 Location in patent: Page/Page column 133
[2]Current Patent Assignee: SANOFI - WO2007/12422, 2007, A1 Location in patent: Page/Page column 62
  • 3
  • [ 923022-43-9 ]
  • [ 824-94-2 ]
  • [ 923022-44-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-bromo-6-fluoro-2H-isoquinolin-1-one With sodium hydride In ISOPROPYLAMIDE at 20℃; for 1h; Stage #2: p-methoxybenzyl chloride In ISOPROPYLAMIDE at 20℃; 9.66 g (39.9 mmol) of 7-Bbromo-6-fluoro-2H-isoquinolin-1-one (95) were dissolved in 180 ml of dimethyl acetamide and 1.92 g (48.0 mmol) of sodium hydride (60%) were added. After 1 h at room temperature a solution of 7.50 g (48.0 mmol) of 4-methoxy benzylchloride in 25 ml of dimethyl acetamide was added. The mixture was stirred at room temperature until complete conversion was achieved. The solvent was removed under reduced pressure, the residue was taken up in saturated sodium bicarbonate solution and extracted three times with dichloromethane. The organic layers were dried with magnesium sulfate and evaporated to yield 16.8 g of a dark oil as crude product, which was stirred in methanol. Filtration of the precipitate gave 6.56 g of the title compound as a yellow solid. The mother liquor was evaporated and the residue purified by preparative HPLC to yield additional 2.62 g of the desired product. Rt = 1.71 min (Method C). Detected mass: 362.3/364.3 (M+H+).
Reference： [1]Current Patent Assignee: SANOFI - WO2007/12422, 2007, A1 Location in patent: Page/Page column 62-63

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