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[ CAS No. 850142-73-3 ] {[proInfo.proName]}

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Chemical Structure| 850142-73-3
Chemical Structure| 850142-73-3
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Product Details of [ 850142-73-3 ]

CAS No. :850142-73-3 MDL No. :MFCD04112568
Formula : C6H5BrFNO Boiling Point : No data available
Linear Structure Formula :- InChI Key :SJOBMIWECHDGAY-UHFFFAOYSA-N
M.W : 206.01 Pubchem ID :46863893
Synonyms :

Safety of [ 850142-73-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 850142-73-3 ]

* 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 [ 850142-73-3 ]

[ 850142-73-3 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 850142-72-2 ]
  • [ 74-88-4 ]
  • [ 850142-73-3 ]
YieldReaction ConditionsOperation in experiment
74% With potassium carbonate; In acetone;Reflux; To a stirring solution of 6-bromo-2-fluoropyridin-3-ol (8.80 g, 45.8 mmol) in acetone (150 mL), potassium carbonate (12.67 g, 91.67 mmol) and iodomethane (5.71 mL, 91.7 mmol) were added. The resulting mixture was stirred under reflux overnight. The contents were filtered and the solvent removed in vacuo to give a residue which was purified by automated normal-phase chromatography (0-30% EtOAc/heptane) to give 6-bromo-2-fluoro-3-methoxypyridine (7.00 g, 34.0 mmol, 74% yield) as a white solid. MS (ES+) m/z 206.0 [M+H]+. XH NMR (400 MHz, CDCI3) δ ppm 7.27 - 7.34 (m, 1H), 7.20 (dd, 1H), 3.88 - 3.95 (m, 3H).
49% With sodium methoxide; In N,N-dimethyl-formamide; at 0 - 20℃; for 12h; To a stirred solution of 6-bromo-2-fluoropyridin-3-ol (4.67 g, 24.3 mmol) and sodium methoxide (1.38 g, 25.5 mmol) in N,N-dimethylformamide (50 mL) was added methyl iodide (1.59 mL, 25.5 mmol) at 0 C, and the mixture was stirred at room temperature for 12 hours. The mixture was treated with H20 and extracted with ethyl acetate. The combined organic layer was dried and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate/ hexane (1: 5 v/v), to afford the titled compound as a yellow oil (2. 43 g, 49 %). 1H) NMR (270MHz, CDC13) 8 = 7.32-7. 26 (m, 1H), 7.22-7. 15 (m, 1H), 3.90 (s, 3H) ppm. MS (EI) ; M+=205, 207
With potassium carbonate; In acetone; at 60℃; for 14h;Inert atmosphere; To a mixture of compound SI23-1 (2.00 g, 10.4 mmol, 1.00 eq) in acetone (30 mL) was added K2CO3 (2.88 g, 20.8 mmol, 2.00 eq) and CH3I (2.96 g, 20.8 mmol, 2.00 eq). The mixture was stirred at 60 C for 14 hrs. under N2 atmosphere. LC-MS (EC1719-5-P1A1) showed one peak (RT = 0.527 min) with desired MS = 205.8. The reaction mixture filtered and concentrated under reduced pressure to give a residue.Compound SI23-2 (2.10 g, crude) was obtained as a yellow solid.LCMS, EC1719-5-P1A1, RT = 0.527 min, M/Z (ESI): 205.8 (M+H)+.
With potassium carbonate; In acetone; at 60℃; for 14h;Inert atmosphere; To a mixture of compound SI23-1 (2.00 g, 10.4 mmol, 1.00 eq) in acetone (30 mL) was added K2CO3 (2.88 g, 20.8 mmol, 2.00 eq) and CH3I (2.96 g, 20.8 mmol, 2.00 eq). The mixture was stirred at 60 C for 14 hrs. under N2 atmosphere. LC-MS (EC1719-5-P1A1) showed one peak (RT = 0.527 min) with desired MS = 205.8. The reaction mixture filtered and concentrated under reduced pressure to give a residue.Compound SI23-2 (2.10 g, crude) was obtained as a yellow solid.LCMS, EC1719-5-P1A1, RT = 0.527 min, M/Z (ESI): 205.8 (M+H)+.

  • 2
  • [ 850142-72-2 ]
  • [ 124-41-4 ]
  • [ 74-88-4 ]
  • [ 850142-73-3 ]
YieldReaction ConditionsOperation in experiment
49% In DMF (N,N-dimethyl-formamide); at 0 - 25℃; for 12h; B. 6-bromo-2-fluoro-3-methoxypyridine; To a stirred solution of 6-bromo-2-fluoropyridin-3-ol (4.67 g, 24.3 mmol) and sodium methoxide (1.38 g, 25.5 mmol) in N, N dimethylformamide (50 mL) was added methyl iodide (1.59 mL, 25.5 mmol) at 0 C, and the mixture was stirred at room temperature for 12 hours. The mixture was treated with H20 and extracted with ethyl acetate. The combined organic layer was dried and evaporated. The residue was purified by chromatography on silica gel, eluting with ethyl acetate/hexane (1: 5 v/v), to afford the titled compound as a yellow oil (2.43 g, 49 %). 'H NMR (270MHz, CD13) 7.32-7. 26 (m, 1H), 7.22-7. 15 (m, 1H), 3.90 (s, 3H) ppm. MS (EI) ; M+=205, 207
  • 3
  • [ 850142-73-3 ]
  • [ 1170045-84-7 ]
  • [ 1438286-73-7 ]
  • 4
  • [ 850142-73-3 ]
  • [ 216854-23-8 ]
  • [ 1527525-25-2 ]
YieldReaction ConditionsOperation in experiment
95% With 4-methyl-morpholine; In 1-methyl-pyrrolidin-2-one; at 120℃;Sealed tube; A mixture of 6-bromo-2-fluoro-3-methoxy-pyridine (2.030 mmo 1; 418.1 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (3.044 mmol; 609.7 mg), and N-Methylmorpholine (6.089 mmol;622 mg; 0.676 mL) in 1-methyl-2-pyrrolidinone (5 mL) in a sealed pressure vial was heated at120 C overnight. The mixture was poured into water, and extracted with EtOAc. The organiclayer was concentrated. The residue was purified on silica eluted with 0 to 40% EtOAc in Heptane to afford tert-butyl N-[(3S)-1-(6-bromo-3-methoxy-2-pyridyl)-3-piperidyl]carbamate(743.5 mg, 95%).
  • 7
  • [ 850142-73-3 ]
  • 6-hydroxy-1,4-diazepane-1,4-diium dibromide [ No CAS ]
  • [ 1527525-36-5 ]
YieldReaction ConditionsOperation in experiment
37% With N,N`-dimethylethylenediamine; In isopropyl alcohol; at 100℃;Sealed tube; A mixture of 6-bromo-2-fluoro-3-methoxy-pyridine (2.660 mmol; 547.9 mg), 1,4-diazepan-6-ol dihydrobromide (3.989 mmol; 1109 mg), and N,N’-diisopropylethylamine (10.64 mmol; 1389 mg; 1.87 mL) in Isopropanol (10 mL) in a sealed pressure vial was heated at 100 C overnight. The mixture was cooled to room temperature and concentrated. The residue was purified on silica eluted with 0 to 10% MeOH in DCM to afford 1-(6-bromo-3-methoxy-2-pyridyl)-1,4-diazepan-6-ol (301. 2mg, 37%).
  • 8
  • [ 850142-73-3 ]
  • 6-hydroxy-1,4-diazepane-1,4-diium dibromide [ No CAS ]
  • [ 1527525-37-6 ]
  • 9
  • [ 174669-74-0 ]
  • [ 850142-73-3 ]
  • 10
  • [ 850142-73-3 ]
  • 6-bromo-2-fluoro-3-methoxypyridin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirring solution of <strong>[850142-73-3]6-bromo-2-fluoro-3-methoxypyridine</strong> (2.70 g, 13.1 mmol) in THF (50 mL) at -78 C, LDA (2 M in THF, 7.86 mL, 15.7 mmol) was added slowly. The resulting mixture was stirred at -78 C for 1 h, then trimethyl borate (1.75 mL, 15.7 mmol) was added portionwise. The resulting mixture was stirred at -78 C for 1 h then allowed to reach room temperature with stirring over 1 h. Hydrogen peroxide (30%, 2.49 mL, 15.7 mmol) was added slowly to the contents, and the resulting mixture was stirred at room temperature for 1 h. Sodium sulfite (5 g) was added, followed by water (50 mL) and 1 N HCI (50 mL) and stirring continued for 1 h. The contents were extracted with EtOAc (2 x 150 mL). The EtOAc extracts were combined, washed with brine (200 mL), dried over Na2S04, filtered and the solvent removed in vacuo to give an off-white solid, which was used without further purification.
  • 11
  • [ 850142-73-3 ]
  • 4-benzyloxy-6-bromo-2-fluoro-3-methoxy-pyridine [ No CAS ]
  • 12
  • [ 850142-73-3 ]
  • 4-benzyloxy-6-fluoro-5-methoxypyridine-2-carbaldehyde [ No CAS ]
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