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[ CAS No. 23612-36-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 23612-36-4
Chemical Structure| 23612-36-4
Chemical Structure| 23612-36-4
Structure of 23612-36-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 23612-36-4 ]

CAS No. :23612-36-4 MDL No. :MFCD08690126
Formula : C7H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :RCDKYXWNDBRDRE-UHFFFAOYSA-N
M.W : 197.03 Pubchem ID :15692030
Synonyms :

Calculated chemistry of [ 23612-36-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.79
TPSA : 28.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : 1.67
Log Po/w (WLOGP) : 2.33
Log Po/w (MLOGP) : 1.07
Log Po/w (SILICOS-IT) : 2.75
Consensus Log Po/w : 1.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.327 mg/ml ; 0.00166 mol/l
Class : Soluble
Log S (Ali) : -1.89
Solubility : 2.56 mg/ml ; 0.013 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0337 mg/ml ; 0.000171 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.49

Safety of [ 23612-36-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23612-36-4 ]

* 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.

  • Upstream synthesis route of [ 23612-36-4 ]
  • Downstream synthetic route of [ 23612-36-4 ]

[ 23612-36-4 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 271-34-1 ]
  • [ 23612-36-4 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: With copper(ll) bromide In acetonitrile at 17 - 20℃; for 1 - 2 h;
Stage #2: With ammonia In methanol; acetonitrile at 10℃;
Example 1 3-bromo-5-azaindole[00145] Referring now to the Scheme 1 as shown in Fig. 1 , a solution of 3.0128g(25.51 mmol) of 5-azaindole (Atlantic SciTech Group) in 50 ml. of acetonitrile 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 17.1Og (76.53 mmol, 3 eg.) of solid CuBr2 was added portion-wise to the flask at 17°C in 10 min. The resulting green suspension was stirred at room temperature until no starting material was observed by TLC (approximately 1-2 hours, Rf = 0.23 for 5-azaindole and 0.49 for 3- bromo-5-azaindole in EtOAc/MeOH=9:1 ). The reaction mixture was cooled to 10°C and then was slowly quenched by addition of IN ammonia in methanol solution (1 1OmL). The resulting blue solution was concentrated on rotavap at room temperature, and the residue was extracted with ethyl acetate (3 x 80 ml_). The organic extract was dried over Na2SO4, filtered, and concentrated to residual volume of about 50 ml_. The temperature of the residue was brought to reflux resulting in the dissolving of all solids, and then hexane was added to the hot mixture until crystallization occured. The resulting suspension was cooled on an ice bath, the product was filtered, washed with cold EtOAc/hexane = 1 :3 and then hexane, and dried. The 3-bromo-5-azaindole was an off- white solid, yield 3.52 g (70percent yield).
32% With copper(ll) bromide In acetonitrile for 1.5 h; 5-Azaindole (118 mg, 1.00 mmol) and copper(II) bromide (669 mg, 3.00 mmol) were mixed with MeCN (10 mL) and stirred for 1.5 h. To the mixture was added 2 M ammonia in MeOH (12 mL) and the resulting suspension was added to water (40 mL) and extracted with EtOAc (2 x 60 mL). The organic layers were combined and washed with brine and evaporated to yield the title compound (190 mg, 32percent). MS (ESI+) m/z = 197, 199 (M+H)+.
32% With copper(ll) bromide In acetonitrile at 20℃; for 1.5 h; 5-Azaindole (118 mg, 1.00 mmol) and copper(II) bromide (669 mg, 3.00 mmol) were mixed with MeCN (10 mL) and stirred for 1.5 h.
To the mixture was added 2 M ammonia in MeOH (12 mL) and the resulting suspension was added to water (40 mL) and extracted with EtOAc (2*60 mL).
The organic layers were combined and washed with brine and evaporated to yield the title compound (190 mg, 32percent). MS (ESI+) m/z=197, 199 (M+H)+.
Reference: [1] Synlett, 2007, # 2, p. 211 - 214
[2] Patent: WO2010/33981, 2010, A2, . Location in patent: Page/Page column 27-28
[3] Patent: WO2011/113798, 2011, A2, . Location in patent: Page/Page column 35
[4] Patent: US2013/102587, 2013, A1, . Location in patent: Paragraph 0181; 0182
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
  • 2
  • [ 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
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