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Chemistry
Heterocyclic Building Blocks
Pyridines
3-Bromo-4-(oxetan-2-yl)pyridine
Chemistry
Heterocyclic Building Blocks
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Pyridines
Oxetanes Bromides

[ CAS No. 1255713-79-1 ] {[proInfo.proName]}

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Chemical Structure| 1255713-79-1
Chemical Structure| 1255713-79-1
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Product Details of [ 1255713-79-1 ]

CAS No. :1255713-79-1 MDL No. :MFCD22573936
Formula : C8H8BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 214.06 Pubchem ID :-
Synonyms :

Safety of [ 1255713-79-1 ]

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Application In Synthesis of [ 1255713-79-1 ]

* 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 [ 1255713-79-1 ]

[ 1255713-79-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1774-47-6 ]
  • [ 70201-43-3 ]
  • [ 1255713-79-1 ]
YieldReaction ConditionsOperation in experiment
Example 28: Synthesis of 2-chloro-4-{4-(oxetan-2-yl)pyridin-3-yl)benzonitrile 28a 28 Step 1·. 3-bromo-4-(oxetan-2-yl)pyridine (28a) A 500 mL round-bottomed flask was charged with trimethylsulfoxonium iodide (1 1.83 g, 53.8 mmol) in DMSO (80 ml), sodium hydride (1.989 g, 49.7 mmol) was added. After stirring for 15min, a solution of 3-biOmoisonicotinaldehyde (5g, 26.9 mmol) in DMSO (20 ml) was added slowly to the reaction. After 10min, The reaction mixture was diluted with water and EtOAc. The mixture was washed with H20 and brine. The organic was dried over Na2S04, filtered and concentrated to give crude intermediate 2.69g without further purification.A 100 mL round-bottomed flask was charged with trimetylsulfoxonium iodide (5.92 g, 26.9 mmol) in t-BuOH (20 ml). Potassium tert-butoxide (3.02 g, 26.9 mmol) was added. After stirring for 15min at 50C, a solution of the above intermediate (2.69g) in DMSO (20 ml) was added slowly to the reaction. After 16h, the reaction mixture was diluted with water and EtOAc. The mixture was extracted with ethyl acetate and washed with H20 and brine to give 462mg of crude title compound. ESI-MS mlz. 216.1 [M+1]+, Retention time 1.01 min;1HNMR (CDCI3, 400.342 MHz) delta ppm 2.50-2.59 (m, 1 H), 3.31-3.39 (m, 1 H), 4.65-4.70 (m, 1H), 4.87-4.92 (m, 1 H), 5.91 (t, J =8 Hz, 1H), 7.95 (d, J = 8 Hz, 1 H), 8.68 (d, J = 8 Hz, 1H), 8.73 (s, 1 H).
Reference： [1]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 72-73
  • 2
  • [ 548797-51-9 ]
  • [ 1255713-79-1 ]
  • [ 1308669-35-3 ]
YieldReaction ConditionsOperation in experiment
9% With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃; for 4h;Inert atmosphere; Step 2: 2-chloro-4-(4-(oxetan-2-yl)pyridin-3-yl)benzonitrile (28) To the solution of 2-chloro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzonitrile (569 mg, 2.16 mmol), 3-bromo-4-(oxetan-2-y I) pyridine (462 mg, 2.16 mmol) andPdCI2(dppf).CH2CI2 adduct (176 mg, 0.216 mmol) in DMF(10ml_) was added a solution of Na2C03. (2 M, 2.70 ml, 5.40 mmol) under Nitrogen atomosphare. The mixture was stirred and heated at 100C for4hrs. Reaction mixture was cooled to room temperature and diluted with EtOAc. The organic layer was washed with water and brine. The aqueous layer was extracted with EtOAc. The combined organic phases were dried with Na2S04, filtered and concentrated in vacuo. Purification by ISCOl2g(0-40%EtOAc Heptane) to give 2-chloro-4-(4- (oxetan-2-yl)pyridin-3-yl)benzonitrile (54 mg, 9%) as colorless solid.; ESI-MS mlz: 271[M+1]+, Retention time 1.42min. 1H-NMR (MeOD, 400 MHz) δ 2.58-2.67 (m, 1 H)r 2.82-2.90 (m, 1 H), 4.61-4.67 (m, 1 H), 4.77-4.83 (m, 1 H), 5.88 (t, J = 7.6 Hz, 1 H), 7.46 (dd, J = 8.0, 1.2 Hz, 1 H ), 7.67 (d, J = 1.2 Hz, 1 H), 7.94 (d, J - 8.0 Hz, 1 H), 7.96 (d, J = 4.8 Hz, 1 H), 8.47 (s, 1 H), 8.74 (d, J = 4.8 Hz, 1H); The racemate was separated by chiral HPLC (ChiralPak AS-H, 40%EtOH/Heptane, v/v) to give 28-(enantiomer-1 ) (retention time: 8.58 min) and 28-{enantiomer-2) (retention time. 12.52 min).
Reference： [1]Patent: WO2011/61168,2011,A1 .Location in patent: Page/Page column 73
  • 3
  • [ 548797-51-9 ]
  • [ 1255713-79-1 ]
  • [ 1308669-37-5 ]
  • [ 1308669-36-4 ]
Reference： [1]Patent: WO2011/61168,2011,A1

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