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[ CAS No. 179897-89-3 ] {[proInfo.proName]}

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Chemical Structure| 179897-89-3
Chemical Structure| 179897-89-3
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Product Details of [ 179897-89-3 ]

CAS No. :179897-89-3 MDL No. :MFCD00143424
Formula : C7H3BrFN Boiling Point : -
Linear Structure Formula :- InChI Key :GYCNHFWRPJXTSB-UHFFFAOYSA-N
M.W :200.01 Pubchem ID :2724900
Synonyms :

Calculated chemistry of [ 179897-89-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 38.81
TPSA : 23.79 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) : -5.79 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.93
Log Po/w (XLOGP3) : 2.43
Log Po/w (WLOGP) : 2.88
Log Po/w (MLOGP) : 2.63
Log Po/w (SILICOS-IT) : 2.9
Consensus Log Po/w : 2.55

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.176 mg/ml ; 0.000881 mol/l
Class : Soluble
Log S (Ali) : -2.57
Solubility : 0.535 mg/ml ; 0.00268 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0481 mg/ml ; 0.00024 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.82

Safety of [ 179897-89-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 179897-89-3 ]

* 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 [ 179897-89-3 ]
  • Downstream synthetic route of [ 179897-89-3 ]

[ 179897-89-3 ] Synthesis Path-Upstream   1~18

  • 1
  • [ 67-56-1 ]
  • [ 179897-89-3 ]
  • [ 127667-01-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3998 - 4001
  • 2
  • [ 67-56-1 ]
  • [ 179897-89-3 ]
  • [ 144649-99-0 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 15, p. 3998 - 4001
  • 3
  • [ 546-88-3 ]
  • [ 179897-89-3 ]
  • [ 177995-39-0 ]
Reference: [1] Patent: US9174994, 2015, B2, . Location in patent: Page/Page column 117
  • 4
  • [ 202865-65-4 ]
  • [ 179897-89-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 1, p. 279 - 282
  • 5
  • [ 201230-82-2 ]
  • [ 179897-89-3 ]
  • [ 171050-06-9 ]
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 18, p. 3131 - 3134
  • 6
  • [ 920-39-8 ]
  • [ 179897-89-3 ]
  • [ 218301-22-5 ]
Reference: [1] Patent: WO2004/20414, 2004, A1, . Location in patent: Page 98-99
  • 7
  • [ 97674-02-7 ]
  • [ 179897-89-3 ]
  • [ 288309-07-9 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In tolueneInert atmosphere; Reflux
Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 4 h;
Example 27A
3-Acetyl-6-fluorobenzenecarbonitrile
Under an argon atmosphere, 449 mg (0.490 mmol) of tris(dibenzylideneacetone)dipalladium and 671 mg (1.078 mmol) of rac-1,1'-binaphthalene-2,2'diylbis(diphenylphosphane) are added to 4.90 g (24.5 mmol) of 3-bromo-6-fluorobenzenecarbonitrile in 180 ml of toluene.
After the addition of 10.6 g (29.4 mmol) of (1-ethoxyvinyl)tributylstannane, the mixture is stirred under reflux overnight.
The reaction mixture is subsequently concentrated and the residue is taken up in 200 ml of THF.
After the addition of an aqueous 2N hydrogen chloride solution (50 ml), the mixture is stirred at room temperature for 4 h.
The reaction mixture is subsequently neutralized using a saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate.
The combined organic phases are dried over magnesium sulfate, filtered and concentrated under reduced pressure.
The crude product is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1→3:1).
3.50 g (88percent of theory) of the title compound are obtained.
1H-NMR (400 MHz, DMSO-d6): δ=8.55 (dd, 1H), 8.31 (ddd, 1H), 7.68 (t, 1H), 2.63 (s, 3H).
GC-MS (Method 11): Rt=4.34 min; MS (EIpos): m/z=163 [M]+.
Reference: [1] Patent: US2013/45999, 2013, A1, . Location in patent: Paragraph 0247; 0248; 0249; 0250
  • 8
  • [ 179897-89-3 ]
  • [ 288067-35-6 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide; potassium acetate In ethyl acetate; acetonitrile a
2-Hydroxyl-4-bromobenzonitrile
A mixture of 2-fluoro-5-bromobenzonitrile (30 g, 152.3 mmole), potassium acetate (222.4 g, 228.5 mmole), and 18-crown-6 ether (60.4 g, 288.5 mmole) in MeCN (400 mL) was heated at reflux in 36 h.
The mixture was cooled, added 2.5 N NaOH (200 mL), stirred at RT overnight.
The mixture was extracted with ether (discarded).
The aqueous layer was acidified with 6N HCl, extracted with EtOAc, dried over MgSO4, concentrated, purified by flash column chromatography (40percent EtOAc/Hex) to give a light yellow foam (24.45 g, 81percent).
1H-NMR (300 MHz, DMSO-d6): δ7.13 (dd, J=1.7, 8.3 Hz, 1H), 7.17 (d, J=1.7 Hz, 1H), 7.61 (d, J=8.3 Hz, 1H).
Reference: [1] Patent: US6417215, 2002, B1,
  • 9
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 179897-89-3 ]
  • [ 676602-31-6 ]
YieldReaction ConditionsOperation in experiment
43% With triethylamine; triphenylphosphine In acetonitrile at 60℃; for 96 h; To CH3CN (100 mL) and MEOH (25 mL) in a sealed tube apparatus is added 5-bromo-2- fluorobenzonitrile (5.00 g, 25. 0 MMOL), TEA (6.97 mL, 50.0 mmol), palladium (II) acetate (393 mg, 1.75 mmol), and triphenylphosphine (269 mg, 1.03 mmol). The reaction is sealed, purged with carbon monoxide twice, and placed under 60 psi of carbon monoxide at 60 C for 4 d. Upon cooling, the reaction is filtered through diatomaceous earth, washing with MeOH. The filtrate is concentrated under reduced pressure, and the residue suspended in 4: 1 EtOAc/Hex (100 mL) then filtered. The filtrate is concentrated under reduced pressure then subjected to flash chromatography (silica gel, CHC13) to afford the sub-title compound (1.91 g, 43percent). 'H NMR (300 MHz, DMSO-d6) 8 3.87 (s, 3H), 7.66 (t, J= 9. 0 Hz, 1H), 8.30 (ddd, J = 2.2, 5.3, 8.6 Hz, 1H), 8.43 (dd, J = 2.2, 6.3 Hz, 1H). FAB MS nez 154 [C9H6FN02 + H-HCN] +, 136 [C9H6FN02 + H-CO2]-
Reference: [1] Patent: WO2004/67529, 2004, A1, . Location in patent: Page 193 - 194
  • 10
  • [ 179897-89-3 ]
  • [ 57260-71-6 ]
  • [ 791846-40-7 ]
YieldReaction ConditionsOperation in experiment
80% With triethylamine In dimethyl sulfoxide at 100℃; In a pressure tube, 5-bromo-2-fluorobenzonitrile (2500 mg, 12.5 mmol), tert-butyl piperazine-1-carboxylate (2444.45 mg, 13.12 mmol), triethylamine (5.23 ml, 37.5 mmol) in dimethylsulfoxide (10 ml) were combined and refluxed at 100 C for ovn. The mixture was cooled, and partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried using sodium sulfate and concentrated. The residue was purified by flash column chromatography on silica gel 5-60percent ethyl acetate/hexane to provide a light brown oil, tert-butyl 4-(4-bromo-2-cyanophenyl)piperazine-1-carboxylate (3660 mg, 80percent).
44% With caesium carbonate In dimethyl sulfoxide at 120℃; for 1 h; A mixture of 1—15 (3.0 g, 14.99 mmcl), 1-Boc-piperizine(3.33 g, 17.99 mmcl) and Cs2003 (9.68 g, 29.98 mci) in DMSO(60 ml) was stirred at 12000 for 1 hour. The reaction mixture was diluted with water (100 mL) and extracted with diethyl ether (100 ml x 3) . The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give thedesired product 1—16 (2.5 g, 44percent) as yellow solid which wasused in the next step without purification; LCMS: m/z 312 [MtBu+1]
Reference: [1] Patent: KR2016/37198, 2016, A, . Location in patent: Paragraph 2392-2394
[2] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 20, p. 5095 - 5098
[3] Patent: WO2017/38909, 2017, A1, . Location in patent: Paragraph 0290; 0291
[4] Patent: WO2009/79593, 2009, A1, . Location in patent: Page/Page column 120
  • 11
  • [ 5419-55-6 ]
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  • [ 214210-21-6 ]
Reference: [1] Patent: US6300352, 2001, B1,
  • 12
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  • [ 214210-21-6 ]
Reference: [1] Patent: WO2006/45350, 2006, A1, . Location in patent: Page/Page column 62-63
  • 13
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  • [ 73183-34-3 ]
  • [ 214210-21-6 ]
Reference: [1] Patent: US6339099, 2002, B1, . Location in patent: Page column 83-86
  • 14
  • [ 179897-89-3 ]
  • [ 73183-34-3 ]
  • [ 775351-57-0 ]
YieldReaction ConditionsOperation in experiment
81% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide at 100℃; Sealed tube 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile
A mixture of 5-Bromo-2-fluoro-benzonitrile (1000.00 mg; 5.00 mmol; 1.00 eq.), 4,4,5,5,4',4',5',5'-Octamethyl-[2,2']bi[[1,3,2]dioxaborolanyl] (1396.61 mg; 5.50 mmol; 1.10 eq.), potassium acetate (1472.07 mg; 15.00 mmol; 3.00 eq.) in dioxane (10 mL) and DMf (1 mL) was degassed, then [1,1']-bis(diphenyl phosphino) ferrocene]dichloropalladium(II), complex with dichloromethane(1:) (366.85 mg; 0.50 mmol; 0.10 eq.) was added and the sealed vial was heated at 100° C. for overnight.
The reaction mixture was cooled and filtered through a pad of Celite.
The solvent was removed and the crude product was purified through flash chromatography on silica gel (EtOAc:hexanes from 0percent to 5percent) to obtain 2-Fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzonitrile (1.0 g, 81percent)
72% With potassium acetate In 1,4-dioxane at 100℃; Inert atmosphere 6(pinacolato)diboron (1.9 g, 7.48 mmol), and KOAc (1.47 g, 14.98 mmol) in 1,4- dioxane (10.0 mL) that was degassed with argon for 10 min was added PdCl2(dppf) (10 mg, 0.014 mmol). The reaction mixture was heated to 100 0C overnight. The reaction mixture was filtered through Celite 521.(R). and rinsed through with EtOAc (10 mL). The filtrate was concentrated in vacuo and treated with CH2Cl2 (10 mL) and water (10 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (5 mL). The combined organic layers were washed with brine (5 mL), dried over Na2SO4, filtered, and concentrated in vacuo onto Isolute.(R).. Purification via flash column chromatography (0- 20percent EtOAc/hexanes) afforded the title compound (1.03 g, 72percent). LC-MS m/z 248 (M+H)+, 1.15 min (ret time).
Reference: [1] Patent: US2016/376283, 2016, A1, . Location in patent: Paragraph 0504; 0505; 0506
[2] Patent: WO2011/25799, 2011, A1, . Location in patent: Page/Page column 50
[3] Organic Letters, 2004, vol. 6, # 19, p. 3265 - 3268
  • 15
  • [ 179897-89-3 ]
  • [ 105-34-0 ]
  • [ 925672-89-5 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 3, p. 487 - 489
  • 16
  • [ 546-88-3 ]
  • [ 179897-89-3 ]
  • [ 455280-00-9 ]
YieldReaction ConditionsOperation in experiment
62%
Stage #1: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 30℃;
Stage #3: With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide
The title compound was prepared by a modification of the literature procedure as described in Palermo, M. G., Tetrahedron Lett, 37:2885 (1996). A single neck 50 mL flask equipped with a magnetic stirred was charged with N-hydroxyacetamide (2.63 g, 35.0 mmol) and DMF (100 mL). Then, KOtBu (3.93 g, 35.0 mmol) was added in one portion. The temperature rose to 300C. The mixture was stirred for Ih and, 5-bromo~2-fluorobenzonitrile (7 g, 35.0 mmol) was added. The reaction mixture was stirred for overnight. A further portion of KOtBu (1.96 g, 17.5mmo) was added and the solution was again stirred overnight. The mixture was poured into brine and CH2CI2 and the layers were separated. The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash column chromatography (BIOTAGE.(R)., eluting with a gradient of 0 to 40percent EtOAc in hexanes) to afford the title compound (4.59 g, 62percent) as a colorless solid. 1H NMR (500 MHz, DMSOd6) δ 8.09 (d, J = 1.8 HZ, IH), 7.65 (dd, J = 2.1, 8.9 Hz, IH), 7.45 (d, J = 8.9 Hz5 IH), 6.49 (s, 2H). LCMS: Anal. Calcd. for C7H5BrN2O: 2115 213; found: 212, 214 (M+H)+.
Reference: [1] Patent: WO2010/138488, 2010, A1, . Location in patent: Page/Page column 57-58
[2] Patent: WO2010/51042, 2010, A1, . Location in patent: Page/Page column 134
[3] Patent: WO2014/151147, 2014, A1, . Location in patent: Paragraph 00502
[4] Patent: US2014/357651, 2014, A1, . Location in patent: Paragraph 0485
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Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 18, p. 7624 - 7643
[2] Patent: WO2006/122799, 2006, A1, . Location in patent: Page/Page column 60-61
[3] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 3, p. 277 - 282
  • 18
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  • [ 763114-25-6 ]
Reference: [1] Patent: CN106905243, 2017, A, . Location in patent: Paragraph 0062; 0063
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