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[ CAS No. 213771-32-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 213771-32-5
Chemical Structure| 213771-32-5
Chemical Structure| 213771-32-5
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Product Details of [ 213771-32-5 ]

CAS No. :213771-32-5 MDL No. :MFCD07375126
Formula : C8H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :KZPOANNAYCXMSH-UHFFFAOYSA-N
M.W :230.06 Pubchem ID :45789787
Synonyms :

Calculated chemistry of [ 213771-32-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.18
TPSA : 39.19 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) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.15
Log Po/w (XLOGP3) : 2.09
Log Po/w (WLOGP) : 1.94
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 2.33
Consensus Log Po/w : 1.98

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.82
Solubility : 0.347 mg/ml ; 0.00151 mol/l
Class : Soluble
Log S (Ali) : -2.54
Solubility : 0.659 mg/ml ; 0.00286 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.35
Solubility : 0.103 mg/ml ; 0.000449 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.84

Safety of [ 213771-32-5 ]

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

Application In Synthesis of [ 213771-32-5 ]

* 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 [ 213771-32-5 ]
  • Downstream synthetic route of [ 213771-32-5 ]

[ 213771-32-5 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 213771-32-5 ]
  • [ 794592-14-6 ]
Reference: [1] Patent: US2014/107109, 2014, A1,
[2] Patent: WO2016/22724, 2016, A1,
  • 2
  • [ 886365-43-1 ]
  • [ 74-88-4 ]
  • [ 213771-32-5 ]
YieldReaction ConditionsOperation in experiment
83% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.666667 h; Step C
methyl 5-bromo-3-methylpyridine-2-carboxylate
To a solution 5-bromo-3-methylpyridine-2-carboxylic acid (2.6 g, 12 mmol) in N,N-dimethylformamide (20.0 mL) was added potassium carbonate (4.99 g, 36.1 mmol) and methyl iodide (1.50 mL, 24.1 mmol) and the reaction was stirred 80° C. for 40 min.
The reaction mixture was partitioned with EtOAc and water.
The organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 2.3 g (83percent yield) of the desired product as a yellow solid.
82% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.666667 h; Example 11.1: methyl S-bromo-S-metliylpyridine-Z-carboxylateO; To a solution of 5-bromo-3-methylpyridine-2-carboxylic acid (450 mg, 2.08 mmol) in dimethylformamide (2 mL) was added potassium carbonate (862 mg, 6.24 mmol) and iodomethane (739 mg, 5.21 mmol) and the reaction was stirred at 80 0C for 40 min. The reaction mixture was partitioned with ethyl acetate and water and the organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated to afford the product as a yellow solid (380 mg, 82percent). 1H NMR (300 MHz, CDCl3): δ 8.91 (s, IH), 7.86 (s, IH), 3.98 (s, 3H), 2.60 (s, 3H).
Reference: [1] Patent: US2013/96144, 2013, A1, . Location in patent: Paragraph 0392; 0393
[2] Patent: WO2008/100715, 2008, A1, . Location in patent: Page/Page column 34
  • 3
  • [ 67-56-1 ]
  • [ 3430-18-0 ]
  • [ 201230-82-2 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: EP977739, 2003, B1, . Location in patent: Page/Page column 9-10
  • 4
  • [ 886365-43-1 ]
  • [ 213771-32-5 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride In methanol for 6 h; Reflux To a mixture of 5-bromo-3-methylpicolinic acid (600 mg, 2.8 mmol) in MeOH (10 mL) was added 50C12 (397 mg, 3.3 mmol). The mixture was stirred at reflux temperature for 6 hours. LCMS showed the reaction was complete. The reaction mixture was evaporated in vacuo to afford methyl 5-bromo-3-methylpicolinate (640 mg, 99percent yield), m/z = 229.76(M+H), as an off-white solid.
Reference: [1] Patent: WO2016/127074, 2016, A1, . Location in patent: Page/Page column 31; 32
  • 5
  • [ 67-56-1 ]
  • [ 886365-43-1 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: WO2011/154677, 2011, A1, . Location in patent: Page/Page column 91-92
[2] Patent: US2016/176882, 2016, A1, . Location in patent: Paragraph 0466; 0467
[3] Patent: WO2017/221100, 2017, A1, . Location in patent: Paragraph 00245
  • 6
  • [ 67-56-1 ]
  • [ 156072-86-5 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: US2006/199817, 2006, A1, . Location in patent: Page/Page column 27
  • 7
  • [ 3430-18-0 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2008/100715, 2008, A1,
  • 8
  • [ 156072-86-5 ]
  • [ 213771-32-5 ]
Reference: [1] Patent: US2013/96144, 2013, A1,
[2] Patent: WO2008/100715, 2008, A1,
  • 9
  • [ 213771-32-5 ]
  • [ 1346809-61-7 ]
Reference: [1] Patent: WO2011/154677, 2011, A1,
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