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Chemical Structure| 1421252-95-0 Chemical Structure| 1421252-95-0

Structure of 1421252-95-0

Chemical Structure| 1421252-95-0

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Product Details of [ 1421252-95-0 ]

CAS No. :1421252-95-0
Formula : C16H23BN2O2
M.W : 286.18
SMILES Code : CC1(C)C(C)(C)OB(C2=C(C(C)C)C=CC3=C2C=NN3)O1
MDL No. :MFCD28400152

Safety of [ 1421252-95-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 1421252-95-0 ]

* 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 [ 1421252-95-0 ]

[ 1421252-95-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 610796-21-9 ]
  • [ 73183-34-3 ]
  • [ 1421252-95-0 ]
YieldReaction ConditionsOperation in experiment
345 mg Example 55-Isopropyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indazole.A suspension of 4-bromo-5-isopropyl-l//-indazole (396 mg, 1.656 mmol), bis(pinacolato)diboron (841 mg, 3.31 mmol), KOAc (488 mg, 4.97 mmol), PdCl2(CH3CN)2 (21.48 mg, 0.083 mmol) and S-Phos (136 mg, 0.331 mmol) in DMSO (6 mL) was allowed to stir at 110 C for 23 h under nitrogen. The reaction mixture was cooled to rt, and diluted with EtOAc and half-saturated brine. The products were extracted three times with EtOAc. The combined organic layer was washed with brine, and concentrated. After the residue was diluted with THF (10 mL) and MeOH (1.5 mL), 1 M aq LiOH (4.5 mL) was added. After stirring for 0.5 h, the reaction was quenched with sat aq NH4C1, and diluted with EtOAc and brine. The mixture was extracted twice with EtOAc. The combined organic layer were washed with a 1 : 1 solution of sat aq NH4C1 and saturated brine, dried over Na2S04, filtered, and concentrated. The residue was purified by flash column chromatography on 40 g of silica gel (0-20% EtO Ac/heptane) to give 5-isopropyl-4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indazole along with 20 mol% of debromonated product (345 mg) as a yellow solid. lH NMR (400 MHz, CDC13, the desired boronic ester) delta ppm 9.93 (br s, 1 H), 8.39 (d, J= 1.01 Hz, 1 H), 7.50 - 7.52 (m, 1 H), 7.41 (d, J= 8.84 Hz, 1 H), 3.75 - 3.85 (m, 1 H), 1.42 (s, 12 H), 1.28 (d, J= 6.82 Hz, 6 H); MS (ESI+) m/z 287.30 (M+H)+. The obtained material was used without further purification.
 

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