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[ CAS No. 192189-16-5 ]

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2D
Chemical Structure| 192189-16-5
Chemical Structure| 192189-16-5
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Product Details of [ 192189-16-5 ]

CAS No. :192189-16-5MDL No. :MFCD16877631
Formula : C12H13BrN2O2 Boiling Point : 388.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :297.15Pubchem ID :57415820
Synonyms :

Computed Properties of [ 192189-16-5 ]

TPSA : 44.1 H-Bond Acceptor Count : 3
XLogP3 : 2.9 H-Bond Donor Count : 0
SP3 : 0.33 Rotatable Bond Count : 2

Safety of [ 192189-16-5 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 192189-16-5 ]

  • Upstream synthesis route of [ 192189-16-5 ]
  • Downstream synthetic route of [ 192189-16-5 ]

[ 192189-16-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 24424-99-5 ]
  • [ 23612-36-4 ]
  • [ 192189-16-5 ]
YieldReaction ConditionsOperation in experiment
97% With dmap In tetrahydrofuran at 17 - 20℃; N-BOC-3-bromo-5-azaindole[00146] Referring now to the Scheme 1 as shown in Fig. 1 , a solution of 3.5601g(18.06 mmol) of 3-bromo-5-azaindole (2) and 0.4651 g (3.8 mmol, 21 molpercent) of dimethylaminopyridine (DMAP) in 80 ml. of THF was placed in a 250 ml. three-neck round-bottom flask equipped with a magnetic stirrer, thermocouple, nitrogen bleed, and cooling ice bath. A total of 4.7769g (21.88 mmol, 1.2 eq.) of BOC2O was added to the flask at 17°C, and the resulting mixture was stirred until starting 3-bromo-5-azaindole disappeared, as monitored by TLC (generally, overnight stirring at room temperature). The resulting yellow solution was concentrated on rotavap, washed with 100 ml. of saturated sodium bicarbonate, and extracted with dichloromethane (3x80 ml_). The organic phase was dried over Na2SO4 and concentrated on rotavap to afford 6.57g of orange solid. This crude material was purified on CombiFlash using hexane/ethyl acetate as eluent to give 5.25g (97percent yield) of n-boc-3-bromo-5-azaindole (3) as a white solid.
90% With dmap In dichloromethane for 1.33333 h; To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert- butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol). After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HC1 (25, 10 mL) and brine. The organic layer was dried (Na2S04), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90percent). MS (ESI+) m/z = 299 (M+H)+.
90% With dmap In dichloromethane at 20℃; for 1.33333 h; To a mixture of Intermediate 1 (1.80 g, 9.14 mmol) in DCM (60 mL) was added di-tert-butyl dicarbonate (2.18 g, 10.0 mmol) followed by 4-dimethylaminopyridine (122 mg, 1.00 mmol).
After 80 min the solution was diluted with DCM (20 mL) and washed with 0.1 M HCl (25, 10 mL) and brine.
The organic layer was dried (Na2SO4), filtered and evaporated to yield the title compound as a light yellow solid (2.47 g, 90percent). MS (ESI+) m/z=299 (M+H)+.
Reference: [1] Patent: WO2010/33981, 2010, A2, . Location in patent: Page/Page column 28
[2] Patent: WO2011/113798, 2011, A2, . Location in patent: Page/Page column 35
[3] Patent: US2013/102587, 2013, A1, . Location in patent: Paragraph 0183; 0184
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
  • 2
  • [ 271-34-1 ]
  • [ 192189-16-5 ]
Reference: [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
[2] Patent: WO2011/113798, 2011, A2,
[3] Patent: US2013/102587, 2013, A1,
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