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Chemical Structure| 1357095-04-5 Chemical Structure| 1357095-04-5

Structure of 1357095-04-5

Chemical Structure| 1357095-04-5

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Product Details of [ 1357095-04-5 ]

CAS No. :1357095-04-5
Formula : C14H22BNO5S
M.W : 327.20
SMILES Code : CS(=O)(NC1=CC=C(B2OC(C)(C)C(C)(C)O2)C(OC)=C1)=O

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Application In Synthesis of [ 1357095-04-5 ]

* 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 [ 1357095-04-5 ]

[ 1357095-04-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 123-75-1 ]
  • [ 1357095-04-5 ]
  • [ 63558-65-6 ]
  • [ 1357094-15-5 ]
YieldReaction ConditionsOperation in experiment
8.8% To a stirred solution of <strong>[63558-65-6]4-chloro-5-iodopyrimidine</strong> (30.6 mg, 0.127 mmol) in DME (1 mL) was added cesium carbonate (83 mg, 0.254 mmol) and pyrrolidine (9.04 mg, 0.127 mmol). The reaction mixture was purged with 2 and heated to 90 C for 12 hours. To this mixture at room temperature was added palladium tetrakis (5.65 mg, 4.89 muiotaetaomicron), Intermediate 51 (32 mg, 0.098 mmol), sodium carbonate (10.37 mg, 0.098 mmol), and additional DME (1.0 mL), EtOH (1.0 mL) and water (1.0 mL). The resulting mixture was purged with 2 and reheated to 90 C. The crude material was purified by preparative HPLC (Column: Waters XBridge CI 8, 19 x 250 mm, 5-muiotaeta particles; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10-mM ammonium acetate; Gradient 10-100% B over 25 minutes, then a 5-minute hold at 100% B; Flow rate 20 mL/min). The collected fractions were combined and dried by centrifugal evaporation. The material was further purified by preparative LC/MS Waters XBridge C18, 19 x 250 mm, 5-muiotaeta particles column; Mobile Phase A: 5:95 acetonitrile:water with 10-mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile: water with 10-mM ammonium acetate; Gradient: 5-70% B over 25 minutes, then alO-minute hold at 70% B; Flow: 20 mL/min. The collected fractions were evaporated to yield the title compound (3.0 mg, 8.8%). MS (ES): m/z = 349.0 [M+H]+. ¾ NMR (400 MHz, MeOD) delta ppm 8.35 (1 H, s), 7.79 (1 H, s), 7.16 (1 H, d, J=7.92 Hz), 6.93 (1 H, d, J=1.98 Hz), 6.89 (1 H, dd, J=8.03, 2.09 Hz), 3.77 (3 H, s), 3.19 (4 H, br. s.), 3.02 (3 H, s).
  • 2
  • [ 1350377-66-0 ]
  • [ 124-63-0 ]
  • [ 1357095-04-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; at 0 - 20℃; for 10h; To a 0 C solution of <strong>[1350377-66-0]3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline</strong> (201mg, 0.807 mmol) in CH2Cl2 (2 mL) was sequentially added pyridine (0.13 mL, 1.61 mmol)and methanesulfonyl chloride (0.10 mL, 148 mg, 1.29 mmol). The reaction mixture wasallowed to reach ambient temperature and stirred for 10 hours. The solution was poured intowater (25 mL) and extracted with EtOAc (2 × 45 mL). The combined organic phase waswashed with saturated aq. NaCl solution (20 mL), dried over anhydrous Na2SO4, filtered andconcentrated in vacuo. This gave 214 mg (0.653 mmol, 76 %) of 10 as white solid, (EtOAc/npentan,1/1, Rf = 0.35). The crude product was used in sub-sequential Suzuki cross-couplingreactions without further purification.
 

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