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Chemical Structure| 1335056-20-6 Chemical Structure| 1335056-20-6

Structure of 1335056-20-6

Chemical Structure| 1335056-20-6

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Product Details of [ 1335056-20-6 ]

CAS No. :1335056-20-6
Formula : C10H11BrClNO2
M.W : 292.56
SMILES Code : O=C(OC(C)(C)C)C1=NC=C(Br)C=C1Cl
MDL No. :MFCD26743625
Boiling Point : No data available

Safety of [ 1335056-20-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1335056-20-6 ]

* 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 [ 1335056-20-6 ]

[ 1335056-20-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 24424-99-5 ]
  • [ 1189513-51-6 ]
  • [ 1335056-20-6 ]
YieldReaction ConditionsOperation in experiment
93% With dmap; In tetrahydrofuran; at 70℃; for 0.5h; To a 50-mL round-bottomed flask was added <strong>[1189513-51-6]5-bromo-3-chloropicolinic acid</strong> (1 g, 4.23 mmol) and di-tert-butyl dicarbonate (1.96 ml, 8.46 mmol) in THF (8.5 ml) followed by addition of 4-(dimethylamino)pyridine (0.052 g, 0.423 mmol). It was heated to 70° C. for 0.5 hr. It was quenched with sat. aq. NaHCO3 and extracted with EtOAc. The organic phase was washed by sat. aq. NaHCO3 and washed with brine and dried over MgSO4. The solution was filtered and concentrated to give the crude material as a yellow oil. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 15percent to 25percent to 35percent (40percent EtOAc in Heptane) in Heptane, to provide tert-butyl 5-bromo-3-chloropicolinate (1.15 g, 3.93 mmol, 93percent yield) as clear colorless oil. MS m/z=314.0/316.0 (M+Na)
With dmap; In tetrahydrofuran; at 60℃; for 3h;Cooling with ice; Acid-19: 3-Chloro-5-difluoromethyl-pyridine-2-carboxylic acid; a) 5-Bromo-3-chloro-pyridine-2-carboxylic acid tert-butyl ester; To an ice cooled solution of 11.82 g (50 mmol) <strong>[1189513-51-6]5-bromo-3-chloro-pyridine-2-carboxylic acid</strong> (CAS 1189513-51-6) in 150 ml THF was added 61 1 mg (5 mmol) DMAP and 14.19 g (65 mmol) Boc20 and the reaction mixture was heated to 60 °C for 3 h. After cooling to 0 °C half saturated aq. sodium bicarbonate was added and the mixture extracted with EtOAc. The combined organic layers were washed with half saturated aq. NaCI, dried with Na2S04 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1 :1) to provide the title compound as colorless oil.HPLC: RtH8= 1.22 min; ESIMS [M-tBu]+ = 237.8;1H-NMR (600 MHz, DMSO-cfe): delta 8.73 (d, 1 H), 8.52 (d, 1 H), 1.55 (s, 9H).
With dmap; In tetrahydrofuran; at 20℃; for 48h; To a solution of <strong>[1189513-51-6]5-bromo-3-chloropicolinic acid</strong> (5.0 g, 21 mmol) in THF (100 mL) at room temperature was added (Boc)20 (9.2 g, 42 mmol) followed by 4-dimethylaminopyridine (0.8 g, 6.3 mmol). The reaction was stirred for 2 days and poured into saturated aqueous NH4CI. The mixture was extracted with DCM. The combined organic layers were dried (MgS04), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (1 column volume of hexanes and then 0-20percent EtO Ac/hex) to provide the title compound Aa2.
 

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