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Product Details of [ 13959-02-9 ]

CAS No. :13959-02-9 MDL No. :MFCD00040944
Formula : C6H4BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :AVXWWBFBRTXBRM-UHFFFAOYSA-N
M.W : 202.01 Pubchem ID :817972
Synonyms :

Calculated chemistry of [ 13959-02-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.9
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.04
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 1.54
Log Po/w (MLOGP) : -0.34
Log Po/w (SILICOS-IT) : 1.43
Consensus Log Po/w : 0.95

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.14
Solubility : 1.45 mg/ml ; 0.00717 mol/l
Class : Soluble
Log S (Ali) : -1.72
Solubility : 3.89 mg/ml ; 0.0193 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.26
Solubility : 1.12 mg/ml ; 0.00555 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.31

Safety of [ 13959-02-9 ]

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 [ 13959-02-9 ]

* 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 [ 13959-02-9 ]
  • Downstream synthetic route of [ 13959-02-9 ]

[ 13959-02-9 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 13959-02-9 ]
  • [ 13958-98-0 ]
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 5, p. 577 - 579
[2] Patent: US2013/217705, 2013, A1,
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
  • 2
  • [ 626-55-1 ]
  • [ 124-38-9 ]
  • [ 13959-02-9 ]
YieldReaction ConditionsOperation in experiment
10%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
3-Bromopyridine30 (164mg, 1.0 mmol) was added to LiNPri2in dry THF (1.0 M, 15 mL, 1.5 mmol) and the mixture was stirred at ‑78°C for 30min under Ar. Crushed solid CO2 was added under Ar, and the coolingwas removed. The mixture was stirred until reaching 20°C. Water (10 mL) was added. The organic solventswere evaporated. The solution was washed thrice with Et2O. Aq. HCl(9 M) was added to pH 3. The mixture was stirred for 1 h and extracted (EtOAc,3 ). Thecombined extracts were washed (brine) and dried. Evaporation gave 31(20 mg, 10percent) as white needles: mp 175-176C (decomp.) (lit.15 mp240°C); 1H NMR d 7.71 (1 H, d, J = 4.8 Hz, 6-H), 8.70 (1 H, d, J = 4.9 Hz,5-H), 8.91 (1 H, s, 2-H) 12.56 (1 H, br, OH); 13C NMR (CDCl3)d 117.26 (4-C), 123.77(6-C), 148.94 (5-C), 152.61 (2-C), 165.00 (C=O), 166.07 (3-C); MS m/z 202 / 200 (M – H)-.
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
[2] Patent: EP2274983, 2011, A1, . Location in patent: Page/Page column 126
[3] Patent: US2011/39843, 2011, A1, . Location in patent: Page/Page column 79
[4] Patent: WO2011/40629, 2011, A1, . Location in patent: Page/Page column 210
[5] Patent: WO2011/49220, 2011, A1, . Location in patent: Page/Page column 209
[6] Patent: WO2011/49223, 2011, A1, . Location in patent: Page/Page column 209
[7] Patent: WO2011/49222, 2011, A1, . Location in patent: Page/Page column 213-214
  • 3
  • [ 3430-22-6 ]
  • [ 13959-02-9 ]
YieldReaction ConditionsOperation in experiment
32% With potassium permanganate In waterHeating / reflux A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62percent) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).
Reference: [1] Patent: US2005/80085, 2005, A1, . Location in patent: Page/Page column 12
[2] Patent: US5294610, 1994, A,
  • 4
  • [ 626-55-1 ]
  • [ 13959-02-9 ]
Reference: [1] Patent: WO2011/49221, 2011, A1, . Location in patent: Page/Page column 210-211
  • 5
  • [ 71541-34-9 ]
  • [ 13959-02-9 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086
  • 6
  • [ 3034-31-9 ]
  • [ 13959-02-9 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086
  • 7
  • [ 67-56-1 ]
  • [ 13959-02-9 ]
  • [ 59786-31-1 ]
YieldReaction ConditionsOperation in experiment
62% Heating / reflux A mixture of 3.98 g of the acid obtained in the previous step (20 mmol, 1 eq.) in 50 ml of methanol is reflux heated in the presence of 4 ml of concentrated sulfuric acid. The mixture is allowed to return to ambient temperature and extracted 3 times with ethyl acetate. The organic phase is dried on Na2SO4 and the solvent is evaporated. 2.65 g (62percent) of esterified product is obtained. NMR (1H, CDCl3): 4.02 (s; 3H), 7.64 (d, J=4.9 Hz; 1H), 8.63 (d, J=4.9 Hz; 1H), 8.88 (s; 1H).
Reference: [1] Patent: US2005/80085, 2005, A1, . Location in patent: Page/Page column 12
[2] Patent: US2010/130477, 2010, A1, . Location in patent: Page/Page column 58
[3] Patent: US2011/230495, 2011, A1, . Location in patent: Page/Page column 23-24
[4] Advanced Synthesis and Catalysis, 2016, vol. 358, # 20, p. 3283 - 3292
  • 8
  • [ 186581-53-3 ]
  • [ 13959-02-9 ]
  • [ 59786-31-1 ]
YieldReaction ConditionsOperation in experiment
66% at 0 - 20℃; for 1 h; Inert atmosphere To a stirred solution of 3-bromoisonicotinic acid 1 (2 g, 9.90 mmol) in MeOH: THF(2: 1, 30 mL) under argon atmosphere was added CH2N2 (2 g, 49.50 mmol) at 0 °C; warmed toRT and stirred for 1 h. The reaction was monitored by TLC; after completion of the reaction, the volatiles were removed in vacuo to obtain the crude. The crude was purified through silica gel column chromatography using 20percent EtOAc/ hexanes to afford compound 2 (1.4 g, 66percent) as brown oil. TLC: 20percent EtOAc/ hexanes (R 0.7); ‘H-NMR (CDC13, 400 MHz): ö 8.87 (s, 1H),8.62 (d, J = 7.2 Hz, 1H), 7.63 (d, J = 5.6 Hz, 1H), 3.97 (s, 3H).
Reference: [1] Patent: WO2018/53157, 2018, A1, . Location in patent: Page/Page column 83
  • 9
  • [ 13959-02-9 ]
  • [ 18107-18-1 ]
  • [ 59786-31-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 14, p. 3878 - 3882[2] Angew. Chem., 2013, vol. 125, # 14, p. 4132
[3] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5820 - 5825
  • 10
  • [ 13959-02-9 ]
  • [ 59786-31-1 ]
Reference: [1] Patent: US5294610, 1994, A,
  • 11
  • [ 13959-02-9 ]
  • [ 74-88-4 ]
  • [ 59786-31-1 ]
Reference: [1] Synthetic Communications, 1997, vol. 27, # 6, p. 1075 - 1086
  • 12
  • [ 13959-02-9 ]
  • [ 76006-17-2 ]
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 5, p. 577 - 579
  • 13
  • [ 541-41-3 ]
  • [ 13959-02-9 ]
  • [ 13959-01-8 ]
  • [ 13958-99-1 ]
YieldReaction ConditionsOperation in experiment
78%
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 1 h;
Stage #2: With ammonia In tetrahydrofuran for 0.25 h;
EtO2CCl (0.58 g, 5.4 mmol) was added dropwise to anice-cold mixture of 31 (1.00 g, 4.6 mmol),dry THF (15 mL) and dry Et3N (1.0 mL). The mixture was stirred for 1h at 0C, then NH3 was bubbled through the suspension for 15 min.The mixture was filtered. The solids were washed with hot Me2CO.The solvent was evaporated from the combined filtrate and washings. Recrystallisation(EtOH) gave 32 as an off-whitepowder (777 mg, 78percent): mp 149-150C; 1H NMR (CDCl3) d 7.48 (1 H, d, J = 4.8 Hz, 5-H), 7.88 (1 H, br, NH),8.11 (1 H, br, NH), 8.65 (1 H, d, J =4.8 Hz, 6-H), 8.84 (1 H, s, 2-H); 13C NMR (CDCl3) d 116.82 (3-C), 122.73(5-C), 146.02 (4-C), 148.58 (6-C), 151.68 (2-C), 167.03 (C=O); MS m/z 224.9469 (M + Na)+(C6H581BrN2NaO requires 224.9457), 222.9485 (M + Na)+(C6H579BrN2NaO requires 222.9477).Evaporation of the solvent from the mother liquor gave 33 (60 mg, 5percent) asa yellow liquid: 1H NMR (CDCl3) d 1.41 (3 H, t, J = 7.2 Hz, Me), 4.43 (2 H, q, J = 7.3 Hz, CH2), 7.59 (1 H,d, J = 4.9 Hz, 5-H), 8.59 (1 H, d, J = 4.9 Hz, 6-H), 8.83 (1 H, s, 2-H); 13CNMR (CDCl3) d 14.04 (Me), 62.33 (CH2),118.71 (3-C), 124.15 (5-C), 139.34 (4-C), 148.41 (6-C), 153.64 (2-C), 164.47(C=O); MS m/z 253.9623 (M + Na)+(C8H881BrNNaO2 requires 253.9611), 251.9638 (M + Na)+(C8H879BrNNaO2 requires 251.9631),224.9469 (M + H)+ (C6H581BrN2Orequires 224.9457), 222.9485 (M + H)+ (C6H579BrN2Orequires 222.9477).
Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 13, p. 3013 - 3032
  • 14
  • [ 13959-02-9 ]
  • [ 13958-99-1 ]
YieldReaction ConditionsOperation in experiment
3.38 g
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 1 h;
Stage #2: With ammonium hydroxide In tetrahydrofuran for 0.666667 h;
Step 1 [0182] To a suspension of 3-bromoisonicotinic acid (1) (4.0 g) in tetrahydrofuran (40 ml) were added oxalyl dichloride (1.82 ml) and dimethylformamide (one drop) at 0° C. and the mixture was stirred for 1 hour. To the reaction solution was added 28percent aqueous ammonia (40 ml) and stirred for 40 minutes. After addition of ethyl acetate to the mixture, the organic layer was washed with brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to afford Compound (2) (3.38 g). [0183] 1H-NMR (DMSO-d6) δ: 7.44 (1H, d, J=4.5 Hz), 7.83 (1H, s), 8.08 (1H, s), 8.60 (1H, d, J=4.5 Hz), 8.79 (1H, s).
Reference: [1] Organic Preparations and Procedures International, 1997, vol. 29, # 5, p. 577 - 579
[2] Patent: US2013/217705, 2013, A1, . Location in patent: Paragraph 0182; 0183
  • 15
  • [ 13959-02-9 ]
  • [ 146679-66-5 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In water at 0℃; for 1 h;
[0281] To a mixture of 3-bromoisonicotinic acid (2.5 g, 12.37 mmol, leq.) and TEA (3.44 mL, 24.75 mmol, 2.0 eq.) in THF (100 mL) was added methyl chloroformate (1.2 mL, 14.85 mmol, 1.2 eq.) at 0 °C. The mixture was stirred at 0 °C for 10 min and filtered. To this filtrate was added a suspension of NaBH4(0.95 g, 24.75 mmol, 2 eq.) in water (1.0 mL) at 0 °C. The mixture was stirred at 0 °C for 1 h, quenched with NH4CI(aq)solution, extracted with EtOAc twice. The combined organic layers were dried over Na2S04, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-bromopyridin-4- yl)methanol (1.2 g, 52percent) as a white solid. 1H NMR (400 MHz, CDC13) δ 8.48 (s, 1H), 8.37 (d, J = 4.9 Hz, 1H), 7.37 (d, J= 4.9 Hz, 1H), 4.61 (d, J= 5.5 Hz, 2H), 2.3 (t, J= 5.5 Hz, 1H). LRMS (M+H+) m/z 188.0.
Reference: [1] Patent: WO2013/102145, 2013, A1, . Location in patent: Paragraph 0281
  • 16
  • [ 13959-02-9 ]
  • [ 79-22-1 ]
  • [ 146679-66-5 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With triethylamine In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 1 h;
Step 1 ;To a mixture of 3-bromoisonicotinic acid (2.5 g, 12.37 mmol, 1 eq.) and TEA (3.44 mL, 24.75 mmol, 2.0 eq.) in THF (100 mL) was added methyl chloroformate (1.2 mL, 14.85 mmol, 1.2 eq.) at 0° C.
The mixture was stirred at 0° C. for 10 min and filtered.
To this filtrate was added a suspension of NaBH4 (0.95 g, 24.75 mmol, 2 eq.) in water (1.0 mL) at 0° C.
The mixture was stirred at 0° C. for 1 h, quenched with NH4Cl(aq) solution, extracted with EtOAc twice.
The combined organic layers were dried over Na2SO4, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give (3-bromopyridin-4-yl)methanol (1.2 g, 52percent) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.48 (s, 1H), 8.37 (d, J=4.9 Hz, 1H), 7.37 (d, J=4.9 Hz, 1H), 4.61 (d, J=5.5 Hz, 2H), 2.3 (t, J=5.5 Hz, 1H). LRMS (M+H+) m/z 188.0.
Reference: [1] Patent: US2015/344483, 2015, A1, . Location in patent: Paragraph 0522; 0523
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