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[ CAS No. 321-23-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 321-23-3
Chemical Structure| 321-23-3
Chemical Structure| 321-23-3
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Product Details of [ 321-23-3 ]

CAS No. :321-23-3 MDL No. :MFCD01930221
Formula : C6H3BrFNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VQCWSOYHHXXWSP-UHFFFAOYSA-N
M.W : 220.00 Pubchem ID :2783362
Synonyms :

Calculated chemistry of [ 321-23-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 42.92
TPSA : 45.82 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) : -5.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.57
Log Po/w (XLOGP3) : 2.45
Log Po/w (WLOGP) : 2.92
Log Po/w (MLOGP) : 2.06
Log Po/w (SILICOS-IT) : 0.81
Consensus Log Po/w : 1.96

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.181 mg/ml ; 0.000822 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.193 mg/ml ; 0.000879 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.266 mg/ml ; 0.00121 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.85

Safety of [ 321-23-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 321-23-3 ]

* 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 [ 321-23-3 ]
  • Downstream synthetic route of [ 321-23-3 ]

[ 321-23-3 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 321-23-3 ]
  • [ 13296-04-3 ]
Reference: [1] Patent: CN105949180, 2016, A,
  • 2
  • [ 321-23-3 ]
  • [ 55687-02-0 ]
Reference: [1] Patent: WO2016/199943, 2016, A1,
  • 3
  • [ 321-23-3 ]
  • [ 337915-79-4 ]
Reference: [1] Patent: WO2011/12622, 2011, A1,
[2] Patent: WO2011/109277, 2011, A1,
[3] Patent: WO2012/21382, 2012, A1,
[4] Patent: US2012/108578, 2012, A1,
[5] Patent: WO2012/174312, 2012, A2,
[6] Patent: WO2013/105676, 2013, A1,
[7] Patent: WO2014/100734, 2014, A1,
[8] Patent: WO2015/200677, 2015, A2,
[9] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 11, p. 2486 - 2503
[10] Patent: WO2016/57834, 2016, A1,
[11] Patent: WO2017/69980, 2017, A1,
[12] Patent: WO2017/176960, 2017, A1,
[13] Patent: WO2007/135527, 2007, A2,
[14] Patent: CN108689942, 2018, A,
  • 4
  • [ 321-23-3 ]
  • [ 55687-34-8 ]
Reference: [1] Patent: WO2016/199943, 2016, A1,
  • 5
  • [ 321-23-3 ]
  • [ 53484-16-5 ]
Reference: [1] Patent: WO2014/100734, 2014, A1,
[2] Patent: WO2015/175845, 2015, A1,
[3] Patent: WO2015/200677, 2015, A2,
  • 6
  • [ 321-23-3 ]
  • [ 367-24-8 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 4, p. 175 - 179
[2] Patent: WO2018/178338, 2018, A1, . Location in patent: Page/Page column 137
  • 7
  • [ 64-17-5 ]
  • [ 321-23-3 ]
  • [ 57279-70-6 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 18 h;
General procedure: Preparation 100: 4-bromo-2-ethoxy-1 -nitrobenzene To a cooled (0°C) solution of EtOH (0.07 mL, 1 .193 mmol) in THF (5 mL) was added NaH (60percent suspension in mineral oil, 68 mg, 1 .705 mmol). The reaction mixture was stirred under nitrogen at 0 for 15 minutes. 2-fluoro-4-bromo-nitrobenzene (250 mg, 1 .136 mmol) was added and the reaction mixture stirred for a further 18 hours, whilst warming slowly to room temperature. The reaction mixture was concentrated in vacuo. Ether (20 mL) and HCI (0.5 M, 20 mL) were added. The aqueous layer was basified with aqueous saturated NaHC03 solution and extracted with EtOAc (3 x 20 mL). The combined organic layers were washed with brine (20 mL), dried (MgS04) and concentrated in vacuo, to give the title compound (270 mg, 97percent). 1 H NMR (500 MHz, CDCI3): δ 7.74 (d, J = 8.5 Hz, 1 H), 7.24 (d, J = 2.0 Hz, 1 H), 7.17 (dd, J = 8.5, 2.0 Hz, 1 H), 4.1 9 (q, J = 7.0 Hz, 2H), 1 .50 (t, J = 7.0 Hz, 3H).
Reference: [1] Patent: WO2014/37750, 2014, A1, . Location in patent: Paragraph 00265; 00266
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 8, p. 3671 - 3688
  • 8
  • [ 321-23-3 ]
  • [ 141-52-6 ]
  • [ 57279-70-6 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 2 h; 4-Bromo-2-fluoro-1-nitro-benzene (15.0 g, 68.2 mmol) was dissolved in ethanol (150 ml), and sodium ethoxide (14.0 g, 205 mmol) was added thereto, followed by stirring at room temperature for 2 hours. The reaction liquid was concentrated under reduced pressure, and then diluted with water. The precipitated solid was filtered and dried under reduced pressure to obtain the title compound (16.0 g, 95percent). [1293] 1H NMR (400 MHz, CDCl3): δ 7.72 (d, J=8.4 Hz, 1H), 7.21 (d, J=1.6 Hz, 1H), 7.15 (dd, J=8.8, 2.0 Hz, 1H), 4.18 (q, J=7.2 Hz, 2H), 1.48 (t, J=7.2 Hz, 3H)
Reference: [1] Patent: US2015/51395, 2015, A1, . Location in patent: Paragraph 1292-1293
  • 9
  • [ 64-17-5 ]
  • [ 321-23-3 ]
  • [ 141-52-6 ]
  • [ 57279-70-6 ]
YieldReaction ConditionsOperation in experiment
90% for 2 h; 62A: 4-bromo-2-ethoxy-l-nitrobenzene; [00479] To a solution of 4-bromo-2-fluoro-l-nitrobenzene (3 g, 13.6 mmol) and EtOH (50 mL) was added NaOEt (21percent w/w, 50 mL). The mixture stirred for 2 h before concentrating in vacuo. The residue purified by flash chromatography (0- 100percent EtoAc/Hexane) to afford 62A (3 g, 90percent) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.49 (t, 3 H) 4.19 (q, 2 H) 7.22 (dd, 2 H) 7.71 - 7.81 (m, 1 H).
Reference: [1] Patent: WO2007/76431, 2007, A1, . Location in patent: Page/Page column 209
  • 10
  • [ 1073-06-9 ]
  • [ 700-36-7 ]
  • [ 321-23-3 ]
Reference: [1] Patent: US2010/280268, 2010, A1, . Location in patent: Page/Page column 22
  • 11
  • [ 321-23-3 ]
  • [ 5228-61-5 ]
YieldReaction ConditionsOperation in experiment
97% With ammonia In methanol at 20℃; for 18 h; 5-Bromo-2-nitro aniline
2-Fluoro-4-bromo-1-nitrobenzene (0.5 g, 2.2 mmol) was added to methanolic ammonia (10 mL) and stirred at r.t. for 18 h.
The reaction mixture was then concentrated in vacuo and the residue was triturated with isohexane, yielding the title compound (0.48 g, 97percent) as a yellow solid. δH (d6-DMSO) 7.88 (d, J 8.8 Hz, 1H), 7.53 (br s, 2H), 7.25 (d, J 3.0 Hz, 1H), 6.75 (dd, J 9.2, 2.0 Hz, 1H).
91% With ammonia In methanol at 0 - 20℃; for 12 h; Sealed tube To a solution of 4-bromo-2-fluoro-1-nitrobenzene (5 g, 22.7 mmol) in MeOH (5 mL), maintained at 0°C in a sealed tube, was added methanolic ammonia (15 mL). The reaction mixture was stirred at room temperature for 12 h, then concentrated. The crude residue was triturated with pentane and Et20 to afford the title compound (4.5 g, 91percent), which was used for the next step without any further purification. H (400 MHz, CD3OD) 7.93 (d,J9.1 Hz, 1H), 7.18 (d,J2.1 Hz, 1H), 6.74 (dd,J9.2, 2.1 Hz, 1H).
Reference: [1] Patent: US2015/152065, 2015, A1, . Location in patent: Paragraph 0498
[2] Patent: WO2015/86508, 2015, A1, . Location in patent: Page/Page column 75; 76
[3] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1939 - 1943
  • 12
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  • [ 59557-91-4 ]
Reference: [1] Patent: US2017/8889, 2017, A1,
  • 13
  • [ 321-23-3 ]
  • [ 62-53-3 ]
  • [ 6311-47-3 ]
YieldReaction ConditionsOperation in experiment
92% at 110℃; 4-Bromo-2-fluoro-nitrobenzene (5.6 g, 20.9 mmol) and aniline (2.5 g, 72.2 mmol) are added to 50 ml. of anhydrous NMP. The reaction is heated to 1 10 °C overnight. After cooling to room temperature and removing the solvent, the compound is purified via column chromatography (silica, cyclohexane/ethyl acetate 9:1 ) and obtained as an orange solid in 92percent yield (5.7 g). H-NMR (400 MHz, CD2CI2): δ = 9.48 (s, 1 H), 8.06 (d, 1 H), 7.46 (t, 2H), 7.30 (t, 4H), 6.89 (d, 1 H).
88% at 50℃; for 30 h; Inert atmosphere 4-bromo-2-fluoronitrobenzene (1.0 g, 4.3 mmol) and aniline (490 mg, 5.2 mmol) are suspended in 1 -methyl-2-pyrrolidon (2 ml_). The mixture is purged with argon, then heated to 50°C for 15 h. Additional aniline (350 mg, 3.7 mmol) is added to the reaction. The mixture is stirred at 50°C for 15 h. After cooling to room temperature the mixture is diluted with 2 ml. of methanol and 15 ml_ of water. The obtained precipitate is filtered and washed twice with methanol/water-solution (2:1 ). The solid is dried at 60°C under vacuum. The desired product is obtained in 88percent yield (1 .1 g). 1H-NMR (400 MHz, CD2CI2): δ = 6.89 (d, 1 H), 7.32-7.26 (m, 3H), 7.33 (s, 1 H), 7.46 (t, 2H), 8.05 (d, 1 H), 9.47 (s, 1 H).
Reference: [1] Patent: WO2015/14944, 2015, A1, . Location in patent: Page/Page column 115; 116
[2] Patent: WO2015/150203, 2015, A1, . Location in patent: Page/Page column 85
[3] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00349
[4] Patent: US2015/30588, 2015, A1, . Location in patent: Page/Page column 71
[5] Patent: US9295673, 2016, B2, . Location in patent: Page/Page column 351; 352
  • 14
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  • [ 124-41-4 ]
  • [ 103966-66-1 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; To a solution of 4-bromo-2-fluoro-1-nitro-benzene (2.0 g, 9.09 mmol) in methanol (50 ml) was added sodium methanolate (30 percent in methanol) (1.64 g, 9.09 mmol). The reac.not. tion mixture was stirred at room temperature overnight. The reaction mixture was con- centrated and the residue was dissolved in water (30 ml) and extracted twice with ethyl acetate. The combined organic phases were washed with water. The organic phase was separated, dried over magnesium sulfate, filtered, and evaporated to dryness to yield a crystalline solid (2.1 g, 99 percent). 1H-NMR (DMSOd6): δ [ppm] 7.9 (d, 1 H), 7.6 (s, 1 H), 7.3 (d, 1 H), 4.0 (s, 3H).
98% at 60℃; for 1 h; MeONa (1.0 mL, 5.0 mmol)Was added to a solution of 4-bromo-2-fluoro-1-nitrobenzene (1.01 g, 4.58 mmol)In MeOH (10mL) solution,The reaction was stirred at 60 ° C in an oil bath for 1 h.The solvent was removed under reduced pressure,The residue was dissolved in CH2Cl2 (30 mL)The insoluble material was removed by filtration,The filtrate was concentrated,To give the object as a yellow solid (1.05 g, 98percent).
89.7% at 20℃; 18.4 g (83.64 mmol) of 2-fluoro-4-bromonitrobenzene (Aldrich) are almost fully dissolved in 300 mL of anhydrous methanol. 19.9 mL (106.22 mmol) of a 30percent solution of sodium methoxide in methanol are added dropwise and the mixture is stirred overnight at room temperature.
The methanol is evaporated off under reduced pressure, the medium is taken up in ethyl acetate and water, and the aqueous phase is then acidified by adding aqueous 1N HCl.
After separation of the phases by settling, the organic phase is washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated under vacuum.
17.4 g of the expected product are obtained in the form of a yellow solid. Yield=89.7percent.
73% at 20℃; for 15 h; 4-Bromo-2-methoxy-1-nitrobenzene (4e). To asolution of 4-Bromo-2-fluoro-1-nitrobenzene (400 mg, 2.0 mmol) in methanol (5 mL) wasadded sodium methoxide 5.0Min methanol (480 L, 2.4 mmol) and then stirred at roomtemperature for 15 h. The reaction mixture was diluted with ethyl acetate, washed with waterand brine, and dried over anhydrous MgSO4. The crude material was purified by silica gelchromatography (6percent ethyl acetate in hexanes) to give 4e (380 mg, 73percent). 1H NMR (600 MHz, Acetone-d6) δ 7.80 (d, J = 8.6 Hz, 1H), 7.53 (d, J = 1.9 Hz, 1H), 7.31 (dd, J = 8.6, 1.9 Hz, 1H),4.04 (s, 3H); 13C NMR (150 MHz, Acetone-d6) δ 154.1, 139.9, 128.4, 127.3, 124.3, 118.3, 57.6;IR (Neat) (cm-1): 3108, 2990, 2957, 2855, 1611, 1567, 1523, 1441, 1396, 1344, 1304, 1258,1189, 1005, 872, 858. 1H NMR data correspond with those reported in the literature [12].
9.5 g at 25℃; for 8 h; Inert atmosphere; Reflux Step 2
4-Bromo-2-methoxy-1-nitrobenzene (compound 12-4)
Compound 12-3 (10.0 g, 46 mmol, commercially available) was dissolved in 150 ml of anhydrous methanol at room temperature, sodium methoxide (4.37 g, 81 mmol) was added, and the reaction mixture was heated to reflux and vigorously stirred for 8 h.
The reaction progress was monitored by TLC.
After completion of the reaction, the reaction mixture was diluted with water, extracted with EA/water system, washed with water for three times, and dried, and the organic layer was concentrated under reduced pressure to give the crude product compound 12-4 (9.5 g) which was used directly in the next step. MS m/z (ESI): 231.0 [M+H]+.

Reference: [1] Patent: WO2006/40182, 2006, A1, . Location in patent: Page/Page column 168
[2] Patent: CN106187838, 2016, A, . Location in patent: Paragraph 0309; 0310; 0311
[3] Patent: US2012/277220, 2012, A1, . Location in patent: Page/Page column 17
[4] PLoS ONE, 2017, vol. 12, # 8,
[5] Patent: US2017/8889, 2017, A1, . Location in patent: Paragraph 0207; 0208
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  • [ 103966-66-1 ]
YieldReaction ConditionsOperation in experiment
9.8 g
Stage #1: With sodium In methanol at 0℃; for 1 h;
Stage #2: at 20℃;
At 0 ° C, sodium metal (1.0 g) was chopped and slowly added to 30 mL.In anhydrous methanol, after 1 h of reaction, 2-fluoro-4-bromo-1-nitrobenzene (10.0 g) was added.After reacting at room temperature overnight, the target product is obtained by post-treatment and separation and purification.(white solid, 9.8 g).
Reference: [1] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 4, p. 175 - 179
[2] Patent: CN108276410, 2018, A, . Location in patent: Paragraph 0164; 0165; 0166
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  • [ 124-41-4 ]
  • [ 103966-66-1 ]
YieldReaction ConditionsOperation in experiment
96% at 60℃; for 1 h; To 4-bromo-2-fluoro-1-nitrobenzene (8.0 g, 36.4 mmol) was added 0.5 N sodium methoxide (105 mL, 52.5 mmol). The mixture was stirred at 60° C. for 1 h. The MeOH was rotovaped down. The crude product was dissolved in DCM (100 mL), washed with H2O, dried (Na2SO4), filtered, and rotovaped down to give the title compound of step A (8.1 g, 34.9 mmol, 96percent) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.74 (d, J=8.61 Hz, 1H), 7.23 (d, J=2.01 Hz, 1H), 7.16 (dd, J=8.61, 1.83 Hz, 1H), 3.95 (s, 3H).
Reference: [1] Patent: US2008/300242, 2008, A1, . Location in patent: Page/Page column 137-138
  • 17
  • [ 321-23-3 ]
  • [ 124840-61-5 ]
Reference: [1] Patent: CN106316923, 2017, A,
  • 18
  • [ 321-23-3 ]
  • [ 305790-48-1 ]
Reference: [1] Patent: WO2012/21382, 2012, A1,
[2] Patent: WO2016/57834, 2016, A1,
  • 19
  • [ 321-23-3 ]
  • [ 1826-67-1 ]
  • [ 883500-73-0 ]
YieldReaction ConditionsOperation in experiment
25% at -40℃; for 1 h; To a solution of 4-bromo-2-fluoro-1-nitrobenzene (1.0 g, 4.54 mmol) in THF (20 mL) was added vinyl magnesium bromide (1M in THF, 13.62 mL, 13.62 mmol) slowly at -40° C.
The reaction mixture was maintained at this temperature for 60 min.
After completion of the reaction saturated aqueous NH4Cl solution was added and the mixture was extracted with EtOAc (2*20 mL).
The combined organic layers were dried over Na2SO4 and evaporated to dryness.
Flash chromatography (silica, EtOAc:petroleum ether 9:1) gave 5-bromo-7-fluoro-1H-indole as a gummy solid (0.24 g, 25percent).
Reference: [1] European Journal of Organic Chemistry, 2006, # 13, p. 2956 - 2969
[2] Patent: US2012/252853, 2012, A1, . Location in patent: Page/Page column 30
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  • [ 1083181-43-4 ]
Reference: [1] Patent: WO2011/12622, 2011, A1,
  • 21
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  • [ 1245649-58-4 ]
Reference: [1] Patent: WO2014/100695, 2014, A1,
[2] Patent: WO2014/100695, 2014, A1,
[3] Patent: WO2014/151147, 2014, A1,
[4] Patent: US2015/30588, 2015, A1,
[5] Patent: US9295673, 2016, B2,
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