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[ CAS No. 886547-94-0 ]

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Chemical Structure| 886547-94-0
Chemical Structure| 886547-94-0
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CAS No. :886547-94-0 MDL No. :MFCD09999194
Formula : C19H21BN2O4S Boiling Point : 565.1°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :384.26 g/mol Pubchem ID :45588137
Synonyms :

Safety of [ 886547-94-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886547-94-0 ]

  • Upstream synthesis route of [ 886547-94-0 ]
  • Downstream synthetic route of [ 886547-94-0 ]

[ 886547-94-0 ] Synthesis Path-Upstream   1~6

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YieldReaction ConditionsOperation in experiment
100% With potassium acetate In N,N-dimethyl-formamide at 90℃; for 2 h; A solution of 3-iodo-1-(phenylsulfonyl)-1 H-pyrrolo[2,3-b]pyridine (4.2 g , 10.9 mmol), bis-pinacolatodiboron (5.6 g, 21.8 mmol), potassium acetate (3.2 g, 32.7 mmol) and Pd(dppf)CI2-complex with dichloromethane (788 mg, 0.982 mmol) inDMF (40 mL) was stirred at 90 0C for 2h in a sealed tube. The solution was cooled by the addition of ice and made basic to pH 12-14 with 6N NaOH. The aqueous phase was extracted with DCM then made acidic to pH ~1 with 6N HCI. The aqeous phase was extracted several times with DCM and the combined fractions were dried (Na2SO4) and concentrated affording the title compound (4.2g, quant.) as a brown solid which was used without further purification; LCMS (m/e) 386 (boronic ester M+H)+, 303 (boronic acid M+H)+.
Reference: [1] Patent: WO2007/76423, 2007, A2, . Location in patent: Page/Page column 53
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YieldReaction ConditionsOperation in experiment
38% With potassium acetate In tetrahydrofuran for 24 h; Heating / reflux A mixture of compound Id (50.78 g), bis(pinacolato)diboron (42.22 g), [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1:1 complex with dichloromethane, 12.32 g) and potassium acetate (44.46 g) in THF (3OO mL) was refluxed for 24 hrs. The. reaction was quenched with water and extracted, with ethyl acetate. The combined organic phase was concentrated and the residue was purified on silica gel column (eluted with 100percent dichloromethane and 2percent methanol in dichloromethane) to provide l-benzenesulfonyl-3-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-lH-pyrrolo[2,3-b]pyridine (Ie) (22.10 g, 38percent) as a white solid. 1H NMR (400MHz, CDCl3) δ 8.42 (d, J = 4.8 Hz, IH), 8.21 (m, 3H), 8.15 (s, IH), 7.57 (t, J = 7.6 Hz, IH), 7.48 (t, J = 7.6 HZ, 2H), 7.35 (dd, J = 8.0 Hz, 4.8 Hz, IH). MS (ESI) m/z: 385 (M+H)+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4818 - 4821
[2] Patent: WO2006/50076, 2006, A1, . Location in patent: Page/Page column 62
[3] Patent: US2011/15173, 2011, A1, . Location in patent: Page/Page column 30
[4] Patent: US2011/257187, 2011, A1, . Location in patent: Page/Page column 22
[5] Patent: US2011/257189, 2011, A1, . Location in patent: Page/Page column 35
[6] Patent: WO2008/5457, 2008, A2, . Location in patent: Page/Page column 103
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Reference: [1] Patent: US2011/257187, 2011, A1,
[2] Patent: US2011/257189, 2011, A1,
[3] Patent: WO2008/5457, 2008, A2,
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 18, p. 4818 - 4821
[2] Patent: WO2008/5457, 2008, A2,
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Reference: [1] Patent: US2011/257187, 2011, A1,
[2] Patent: US2011/257189, 2011, A1,
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Reference: [1] Patent: WO2008/5457, 2008, A2,
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