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Chemical Structure| 39856-58-1
Chemical Structure| 39856-58-1
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Product Details of [ 39856-58-1 ]

CAS No. :39856-58-1 MDL No. :MFCD00234064
Formula : C5H5BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :HKDVVTLISGIPFE-UHFFFAOYSA-N
M.W : 173.01 Pubchem ID :642816
Synonyms :

Calculated chemistry of [ 39856-58-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.34
TPSA : 38.91 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) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.33
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : 1.19

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.03 mg/ml ; 0.00597 mol/l
Class : Soluble
Log S (Ali) : -1.61
Solubility : 4.21 mg/ml ; 0.0243 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.531 mg/ml ; 0.00307 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.75

Safety of [ 39856-58-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 39856-58-1 ]

* 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 [ 39856-58-1 ]
  • Downstream synthetic route of [ 39856-58-1 ]

[ 39856-58-1 ] Synthesis Path-Upstream   1~26

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Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Synthesis, 2001, # 14, p. 2175 - 2179
  • 2
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Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 3
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  • [ 39856-58-1 ]
YieldReaction ConditionsOperation in experiment
100% With iron; ammonium chloride In tetrahydrofuran; water at 60 - 70℃; for 5 h; Preparation Example S-1.
3-Amino-2-bromopyridine
2-Bromo-3-nitropyridine (3g, 15mmol) was dissolved in a mixture solution of tetrahydrofuran (15mL) and water (5mL), then iron powder (1 g, 18mmol) and ammonium chloride (2g, 37mmol) were added thereto, followed by stirring at from 60°C to 70°C for 5 hours.
After the reaction was completed, the reaction mixture was filtered through Celite pad, brine was added, and the solution was extracted with ethyl acetate.
The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting residue was purified by silica gel column chromatography (ethyl acetate: hexane =1:4), and the title compound (2.6g, 15mmol, quantitatively) was obtained.
1H-NMR Spectrum (DMSO-d6) δ(ppm): 5.47 (2H, brs), 7.07-7.09 (2H, m), 7.54 (1H, dd, J=2.0, 3.6Hz).
100% With aluminum (III) chloride; iron In tetrahydrofuran; water 2-Bromo-3-nitropyridine (3g, 15mmol) was dissolved in a mixture solution of tetrahydrofuran (15mL) and water (5mL), then iron powder (1g, 18mmol) and ammonium chloride (2g, 37mmol) were added thereto, followed by stirring at from 60°C to 70°C for 5 hours. After the reaction was completed, the reaction mixture was filtered through Celite pad, brine was added, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting residue was purified by silica gel column chromatography (ethyl acetate : hexane = 1 : 4), and the title compound (2.6g, 15mmol, quantitatively) was obtained. 1H-NMR Spectrum (DMSO-d6) δ(ppm) : 5.47 (2H, brs), 7.07-7.09 (2H, m), 7.54 (1H, dd, J=2.0, 3.6Hz).
Reference: [1] Patent: EP1782811, 2007, A1, . Location in patent: Page/Page column 63
[2] Patent: EP1669348, 2006, A1, . Location in patent: Page/Page column 71
[3] Bulletin de la Societe Chimique de France, 1992, # 1, p. 79 - 84
[4] Journal of the Chemical Society, 1952, p. 2042,2044
[5] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 4
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Reference: [1] Tetrahedron, 1983, vol. 39, # 12, p. 2009 - 2021
  • 5
  • [ 462-08-8 ]
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  • [ 39856-57-0 ]
Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Synthesis, 2001, # 14, p. 2175 - 2179
  • 6
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Reference: [1] Patent: US2003/171395, 2003, A1,
  • 7
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Reference: [1] Patent: WO2005/113552, 2005, A1, . Location in patent: Page/Page column 22
[2] Chemistry - A European Journal, 2014, vol. 20, # 50, p. 16759 - 16763
  • 8
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Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
  • 9
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Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
  • 10
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  • [ 42242-11-5 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
  • 11
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  • [ 7689-62-5 ]
Reference: [1] Patent: US2013/225552, 2013, A1,
  • 12
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  • [ 10261-82-2 ]
Reference: [1] Chemical & Pharmaceutical Bulletin, 1985, vol. 33, # 11, p. 4764 - 4768
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5521 - 5527
[3] Patent: US2013/225552, 2013, A1,
  • 13
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Reference: [1] Synthesis, 2001, # 14, p. 2175 - 2179
[2] Synthesis, 2001, # 14, p. 2175 - 2179
  • 14
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  • [ 50608-99-6 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 2042,2044
  • 15
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  • [ 98-80-6 ]
  • [ 101601-80-3 ]
YieldReaction ConditionsOperation in experiment
84% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 95℃; for 16 h; Sealed tube Example 1 1 -(trans-i -(2-methoxyethyl)-4-phenylpyrrolidin-3-yl)-3-(2-phenylpyridin-3-yl)urea1005771 Step A: Preparation of 2-phenylpyridin-3-amine: Phenyl boronic acid (92 mg,0.75 mmol), K2C03 (320 mg, 2.31 mmol) and Pd(PPh3)4 (67 mg, 0.06 mmol) were combined in toluene (3 mL), water (1.5 mL) and EtOH (0.75 mL) then treated with 2-bromopyridin-3- amine (100 mg, 0.58 mmol). The mixture was warmed to 95 °C in a sealed tube for 16 hours then cooled and partitioned between EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc (2 x 10 mL) and the combined organic phases were washed with brine (10 mL), dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified by silica column chromatography eluting with 9:1 to 4:1 hexanes/EtOAc, to afford 2- phenylpyridin-3-amine (83 mg, 84percent yield) as a pale yellow gum. MS (apci) mlz = 171.2 (M+H).
82% With potassium phosphate; tetrabutylammomium bromide In water at 85℃; for 1 h; Green chemistry General procedure: To a 10-mL reaction vial, heteroaryl halide (1.0 mmol), boronic acid (1.2 mmol), K3PO4 (2.0 mmol), tetra-butylammonium bromide (TBAB) (0.5 mmol), and 4 (0.1 mol percent) in water (3.5 mL) were added. The reaction mixture was stirred at 85 °C and the reaction progress was monitored by GC–MS analysis. After completion of the reaction, it was diluted with H2O and CH2Cl2. The organic layer was separated from mixture, the dried organic layer over MgSO4, and evaporated under reduced pressure. The crude reaction product was purified using column chromatography on silica-gel to afford the corresponding product with isolated yield up to 98percent.
Reference: [1] Patent: WO2014/78378, 2014, A1, . Location in patent: Paragraph 00577
[2] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 9, p. 1478 - 1485
[3] Organic Letters, 2014, vol. 16, # 4, p. 1260 - 1263
[4] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8520 - 8529
[5] Organic Letters, 2017, vol. 19, # 6, p. 1442 - 1445
[6] New Journal of Chemistry, 2017, vol. 41, # 24, p. 15420 - 15432
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YieldReaction ConditionsOperation in experiment
55%
Stage #1: With bis-triphenylphosphine-palladium(II) chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; di(1-adamantyl)benzylphosphonium hydrobromide In dimethyl sulfoxide at 100℃; for 1 h; Schlenk technique; Inert atmosphere
Stage #2: With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 100℃; for 0.25 h; Schlenk technique; Inert atmosphere
General procedure: 3-Amino-2-bromopyridine (1a) (87 mg, 0.5 mmol) or2-bromoaniline (1b) (172 mg, 1.00 mmol), Pd(PPh3)2Cl2(9.0 mg, 13 mmol or 17.5 mg, 25.0 mmol), and(1-Ad)2PBn·HBr (12 mg, 25 mmol or 23.6 mg, 50.0 mmol)were placed into a dry screw-cap Schlenk tube with amagnetic stirring bar, and the vessel was evacuated. Afterflushing the vessel with nitrogen, dry DMSO (1.0 or 1.5 ml),the corresponding alkyne 2a–j (0.6 mmol or 1.2 mmol),and DBU (225 mg, 1.50 mmol or 457 mg, 3.00 mmol)were added. The reaction mixture was stirred at 100°Cunder nitrogen for 1 h until the bromide was completelyconsumed (monitored by TLC). After cooling to roomtemperature, KOt-Bu (253 mg, 2.25 mmol or 281 mg,2.50 mmol) and DMSO (0.50 or 1.00 ml) were added to thereaction mixture, and the mixture was stirred at 100°Cunder nitrogen for 0.25 h. After cooling to roomtemperature, deionized water or brine (20 ml) was added tothe mixture. The aqueous layer was extracted several timeswith EtOAc or CH2Cl2. The combined organic phases weredried over anhydrous Na2SO4 and after filtration, thesolvents were removed under reduced pressure. The residuewas purified by flash chromatography on silica gel to givethe analytically pure products 3a–j. 2-Phenyl-1H-pyrrolo[3,2-b]pyridine (3a) was synthesizedfrom 3-amino-2-bromopyridine (1a) (87 mg, 0.5 mmol)and phenylacetylene (2a) (61 mg, 0.6 mmol), eluent forflash chromatography EtOAc–n-hexane, 3:2. Yield 53 mg(55percent), beige solid, mp 249°C. IR spectrum, ν, cm–1: 3082(w), 3053 (w), 3011 (w), 2969 (w), 2932 (w), 1603 (w),1568 (w), 1537 (w), 1481 (w), 1456 (m), 1414 (m), 1362 (m),1343 (m), 1289 (w), 1275 (m), 1227 (w), 1200 (w), 1173 (w),1157 (w), 1119 (w), 1096 (w), 1074 (w), 1053 (w), 1030 (w),988 (w), 924 (m), 910 (w), 833 (w), 810 (w), 785 (m), 766 (s),735 (m), 687 (s). 1H NMR spectrum, δ, ppm (J, Hz): 7.06(1H, s, H-3); 7.10 (1H, dd, J = 8.0, J = 4.6, H-6); 7.37–7.38(1H, m, H Ph); 7.48–7.50 (2H, m, H Ph); 7.77 (1H, d, J = 8.0, H-7); 7.92–7.93 (2H, m, H Ph); 8.31–8.32 (1H, m,H-5); 11.82 (1H, br. s, NH). 13C NMR spectrum, δ, ppm:99.2 (CH); 116.8 (CH); 118.3 (CH); 125.5 (CH); 128.4(CH); 129.2 (CH); 130.1 (C); 131.7 (C); 141.1 (C); 142.9(CH); 146.9 (C). Mass spectrum, m/z (Irel, percent): 195 (14),194 [M]+ (100), 193 (25), 192 (7), 167 (6), 166 (8), 97 (11).Found, m/z: 195.0920 [M+H]+. C13H11N2. Calculated, m/z:195.0917.
Reference: [1] Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 3, p. 334 - 338[2] Khim. Geterotsikl. Soedin., 2018, vol. 54, # 3, p. 334 - 338,5
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Reference: [1] Organic Letters, 2016, vol. 18, # 13, p. 3250 - 3253
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Reference: [1] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5316 - 5319
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Reference: [1] Patent: EP1479680, 2004, A1, . Location in patent: Page 48
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Reference: [1] Tetrahedron, 1983, vol. 39, # 12, p. 2009 - 2021
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1182 - 1185
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YieldReaction ConditionsOperation in experiment
10.7%
Stage #1: at 130℃; for 15 h;
Stage #2: at 20℃; for 1 h;
3-Amino-2-bromopyridine (1.14 g, 6.59 mmol) and ethyl potassium xanthate (2.324 g, 14.50 mmol) were dissolved in dry dimethylformamide (4 mL) and heated at 130° C. for 15 hours. The reaction was cooled and diluted with water (150 mL). 5 N Hydrochloric acid (4 mL) was added and the mixture stirred. The intermediate precipitated as a light yellow solid and was filtered off. The solids were suspended in warm ethyl acetate (200 mL) and dried with magnesium sulfate. The filter cake was washed with additional warm ethyl acetate (200 mL). The organic was evaporated to dryness under reduced pressure and suspended in dichloromethane (50 mL). Sulfuryl chloride (20 ml, 247 mmol) was added and the mixture stirred at room temperature. After 1 hour, the mixture was evaporated to dryness under reduced pressure and the residue partitioned between ethyl acetate (200 mL), ice (50 mL), water (100 mL) and saturated sodium bicarbonate (60 mL). The organic phase was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired 2-chlorothiazolo[5,4-b]pyridine (0.120 g, 0.703 mmol, 10.7percent yield).
Reference: [1] Patent: US2013/225552, 2013, A1, . Location in patent: Paragraph 0494
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Reference: [1] Patent: WO2013/64231, 2013, A1,
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YieldReaction ConditionsOperation in experiment
62%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: at 20℃; for 1.5 h;
Step 1 : fert-Butyl 2-bromopyridin-3-ylcarbamate (10a)To a solution of 2-bromopyridin-3-amine (3.0 g, 17.3 mmol) in THF (30 mL) was added lithium bis(trimethylsilyl)amide (1 M, 35 mL, 35 mmol) slowly at 0°C and the mixture was stirred at this temperature for 30 min. (Boc)20 (3.9 g, 17.3 mmol) in THF (20 mL) was added and the mixture was stirred at rt for 1.5 h. The reaction mixture was poured into 0.1 M of HCI and extracted with EA. The combined organic layers were extracted with brine, dried and concentrated under reduced pressure. The crude product was purified by CC (PE/EA = 5/1) to give compound 10a (2.9 g, 62percent) as a white solid.
50.7%
Stage #1: With dmap In tetrahydrofuran for 3 h; Reflux
Stage #2: With potassium carbonate In tetrahydrofuran; methanol at 20℃; for 3 h; Reflux
Example 120A
tert-butyl 2-bromopyridin-3-ylcarbamate
To a solution of 2-bromopyridin-3-amine (5.0 g, 28.9 mmol) in THF (50 mL) was added Boc2O (18.92 g, 87 mmol) and DMAP (0.353 g, 2.89 mmol).
The resulting mixture was refluxed for about 3 hours, cooled to room temperature and K2CO3 (11.98 g, 87 mmol) and 50 mL of MeOH were added respectively.
The resulting mixture was stirred at reflux for about 3 hours, then cooled to room temperature, filtrated, and concentrated to give the crude product.
The residue was chromatographed on silica gel column (50:1 Hexanes/EtOAc) to afford the product as a white solid (4.0 g, yield: 50.7percent).
1H NMR (400 MHz, CDCl3): δ 8.45-8.47 (d, 1H, J=8 Hz), 7.02-8.03 (d, 1H, J=4.4 Hz), 7.23-7.26 (m, 1H), 7.05 (s, 1H), 1.55 (s, 9H).
50.7%
Stage #1: With dmap In tetrahydrofuran for 3 h; Reflux
Stage #2: With methanol; potassium carbonate In tetrahydrofuran for 3 h; Reflux
tert-butyl 2-bromopyridin-3-ylcarbamate[204] To a solution of 2-bromopyridin-3-amine (5.0 g, 28.9 mmol) in THF (50 mL) was added Boc20 (18.92 g, 87 mmol) and DMAP (0.353 g, 2.89 mmol). The resulting mixture was refluxed for about 3 hours, cooled to room temperature and K2CO3 (1 1.98 g, 87 mmol) and 50 mL of MeOH were added respectively. The resulting mixture was stirred at reflux for about 3 hours, then cooled to room temperature, filtrated, and concentrated to give the crude product. The residue was chromatographed on silica gel column (50: 1 Hexanes/EtOAc) to afford the product as a white solid (4.0 g, yield: 50.7 percent). *H NMR (400 MHz, CDCI3): ? 8.45-8.47 (d, IH, J= 8 Hz), 7.02-8.03 (d, IH, J= 4.4 Hz), 7.23-7.26 (m, IH), 7.05 (s, IH), 1.55 (s, 9H).
Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 16, p. 5032 - 5043
[2] Patent: WO2013/64231, 2013, A1, . Location in patent: Page/Page column 51
[3] Patent: US2013/131036, 2013, A1, . Location in patent: Paragraph 1676; 1677
[4] Patent: WO2013/62966, 2013, A2, . Location in patent: Paragraph 203; 204
[5] Patent: WO2005/21529, 2005, A1, . Location in patent: Page/Page column 31
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Reference: [1] Patent: WO2009/140642, 2009, A2, . Location in patent: Page/Page column 85
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Reference: [1] Patent: US6281227, 2001, B1,
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Reference: [1] Tetrahedron, 2002, vol. 58, # 17, p. 3323 - 3328
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