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Chemical Structure| 537032-06-7 Chemical Structure| 537032-06-7

Structure of 537032-06-7

Chemical Structure| 537032-06-7

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Product Details of [ 537032-06-7 ]

CAS No. :537032-06-7
Formula : C11H14ClNO3
M.W : 243.69
SMILES Code : O=C(C1=CC(Cl)=NC(OC)=C1)OC(C)(C)C

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Application In Synthesis of [ 537032-06-7 ]

* 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 [ 537032-06-7 ]

[ 537032-06-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 15855-06-8 ]
  • [ 36805-97-7 ]
  • [ 537032-06-7 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 80 - 100℃; for 48h; A solution of 10.0 g (53.3 mmol) 2-Chloro-6-methoxy-isonicotinic acid in 60 ml DMF is heated to 100 C. for 4 h, then to 80 C. for another 44 h. In total 99 ml (410 mmol, 7.8 eq) N,N-dimethylformamide di-tert-butylacetal is added in 12 portions over time. After cooling to rt the mixture is diluted with EtOAc, washed with aq. bicarbonate and brine, and dried over sodium sulfate. The residue is purified by chromatography on silica (flashmaster, hexane to hexane/EtOAc 95/5) to give the product in the form of a white solid.MS (LC/MS): 188=[M+H-tBu]+ 1H-NMR (300 MHz, CDCl3): 7.37 (s, 1H), 7.16 (s, 1H), 3.97 (s, 3H), 1.59 (s, 9H).
  • 2
  • [ 15855-06-8 ]
  • [ 24424-99-5 ]
  • [ 537032-06-7 ]
YieldReaction ConditionsOperation in experiment
96% With dmap; In dichloromethane; tert-butyl alcohol;Inert atmosphere; A 100 mL round bottom flask was charged with 2-chloro-6-methoxypyridine-4- carboxylic acid (0.75 g, 4.0 mmol, 1 eq) and a stir bar. The flask was evacuated and back- filled with Ar (x3). Anhydrous DCM (20 mL) was added followed by tBuOH (3.8 mL, 2.96 g, 40 mmol, 10 eq). The resulting stirred solution was treated sequentially with (Boc)20 (1.4 mL, 1.3 g, 6.0 mmol, 1.5 eq) and DMAP (0.0977g, 0.8 mmol, 0.2 eq). The reaction was stirred overnight. The reaction was washed with NaHCO3 (aq, saturated, xl), brine (xl), and dried over Na2 SO4. The solution was plug filtered through silica gel eluting with additional DCM. The volatiles were removed via rotary evaporation yielding 0.936 g (3.8 mmol, 96% yield) of 44.
 

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