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[ CAS No. 17100-65-1 ] {[proInfo.proName]}

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Chemical Structure| 17100-65-1
Chemical Structure| 17100-65-1
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Product Details of [ 17100-65-1 ]

CAS No. :17100-65-1 MDL No. :MFCD12026001
Formula : C9H9BrO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MGIYCRUAYQQSNL-UHFFFAOYSA-N
M.W :245.07 Pubchem ID :15110997
Synonyms :

Calculated chemistry of [ 17100-65-1 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.91
TPSA : 35.53 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) : -6.04 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 2.47
Log Po/w (WLOGP) : 2.24
Log Po/w (MLOGP) : 2.36
Log Po/w (SILICOS-IT) : 2.39
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.214 mg/ml ; 0.000873 mol/l
Class : Soluble
Log S (Ali) : -2.86
Solubility : 0.338 mg/ml ; 0.00138 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.085 mg/ml ; 0.000347 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.64

Safety of [ 17100-65-1 ]

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 [ 17100-65-1 ]

* 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 [ 17100-65-1 ]
  • Downstream synthetic route of [ 17100-65-1 ]

[ 17100-65-1 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 17100-65-1 ]
  • [ 74317-85-4 ]
Reference: [1] Patent: WO2014/4902, 2014, A2, . Location in patent: Sheet 30
  • 2
  • [ 67-56-1 ]
  • [ 74317-85-4 ]
  • [ 17100-65-1 ]
YieldReaction ConditionsOperation in experiment
94% at 0℃; for 16 h; Reflux A stirred solution of 2-Bromo-4-methoxy -benzoic acid (5) (1.0 g, 4.329 mmol) in MeOH (15 mL) was cooled to 0°C and to it Thionyl chloride (3.14 mL, 43.29 mmol) was added drop wise. The reaction mixture was then refluxed for 16 hours. It was then evaporated to dryness and the residue was dissolved in EtOAc, washed with saturated sodium bicarbonate solution and brine. The organic layer was dried over sodium sulfate and concentrated to afford Intermediate 6 (1.0 g; 94percent) as colorless liquid.
91% at 0 - 20℃; for 2 h; Heating / reflux In an ice bath, thionyl chloride (2.9 mL, 38.7 mmol) is slowly added dropwise into a solution of 2-bromo-4-methoxy benzoic acid (IV) (4.5 g, 19.3 mmol) in methanol (10 mL). Then the temperature of the mixture is allowed to reach the room temperature. The reaction mixture is then heated in reflux while reaction is monitored by TLC. The reaction is completed after 2 hrs. Excess thionyl chloride and methanol are evaporated. The residue is diluted with ethyl acetate, and is washed with water and then with saturated aqueous sodium carbonate. The organic phase is dried over anhydrous magnesium sulfate to give the product (V) (4.3 g, 91percent).1H NMR (CDCl3, 400 MHz) 7.87 (d, J=9.2 Hz, 1H, Ar-H), 7.19 (d, J=2.0 Hz, 1H, Ar-H), 6.87 (dd, J=9.2, 2.0 Hz, 1H, Ar-H), 3.90 (s, 3H, OCH3), 3.84 (s, 3H, OCH3).
85% at 0 - 79℃; SOCl2 (7.5 mL, 103.0 mmol) is added dropwise to a stirred 0 °C suspension of 2-bromo-4-methoxybenzoic acid (3) (6.5 g, 28.1 mmol) in methanol (12 mL). The mixture is next stirred at 79 °C for 18 h and then cooled to room temperature before removal of methanol and excess SOCl2 at reduced pressure. The residue is diluted with H2O (50 mL) and extracted with ethyl acetate (100 mL and 70 mL). The extract is washed (2 N NaOH and brine) and dried. After solvent removal at reduced pressure, the residue is purified on silica gel (14.3percent to 16.7percent ethyl acetate/hexane) to give 5.9 g (85percent) of 4 as a colorless liquid. IR 2952, 1728, 1597, 1261 cm"1; 1H NMR (CDCl3) δ 3.83 (s, 3H, CH3O), 3.89 (s, 3H, CO2CH3), 6.86 (dd, J= 7.2, 2.0 Hz, IH, 5-PhH), 7.18 (d, J= 2.0 Hz, IH, 3-PhH), 7.85 ppm (d, J= 7.2 Hz, IH, 6-PhH).
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4083 - 4086
[2] Tetrahedron Asymmetry, 2008, vol. 19, # 4, p. 482 - 488
[3] Patent: WO2018/175324, 2018, A1, . Location in patent: Page/Page column 118
[4] Patent: US2009/156829, 2009, A1, . Location in patent: Page/Page column 4
[5] Patent: WO2010/33643, 2010, A2, . Location in patent: Page/Page column 79; 80; 81
[6] Tetrahedron Letters, 2007, vol. 48, # 24, p. 4179 - 4182
[7] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0478
  • 3
  • [ 101085-03-4 ]
  • [ 74-88-4 ]
  • [ 17100-65-1 ]
YieldReaction ConditionsOperation in experiment
95.9% With potassium carbonate In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide Example 7
Methyl 2-bromo-4-methoxybenzoate (Compound 11)
Compound 10 (815 mg, 3.54 mmol) was dissolved in DMF (20 mL). K2CO3 (1.17 g, 8.50 mmol) was added, then the reaction mixture was stirred at room temperature for 20 min.
The reaction mixture was cooled to 0° C., a solution of iodomethane (265 μL, 4.25 mmol) in DMF (1 mL) was added dropwise, and then the reaction was stirred at room temperature for 2 h.
The reaction was quenched by adding H2O (50 mL), then partitioned with Et2O (200 mL).
The Et2O layer was washed with H2O (3*40 mL) and brine (40 mL).
The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated, and purified by silica column chromatography (15percent EtOAc in hexanes) to afford compound 11 in 95.9percent (849 mg) yield as a brown liquid. 1H-NMR (CDCl3, 400 MHz) δ 7.87 (1H, d, J=8.4 Hz, Ar), 7.19 (1H, s, Ar), 6.88 (1H, d, J=8.4 Hz, Ar), 3.90 (3H, s, OCH3), 3.84 (3H, s, OCH3); 13C-NMR (CDCl3, 100 MHz) δ 165.8, 162.2, 133.1, 123.5, 123.3, 119.7, 113.0, 55.6, 52.1; MS (ESI) m/z Calcd for C9H9BrO3 (M+): 244.0, Found: 244.1 (M+).
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1, . Location in patent: Page/Page column
  • 4
  • [ 100959-22-6 ]
  • [ 17100-65-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1,
  • 5
  • [ 98545-64-3 ]
  • [ 17100-65-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1,
  • 6
  • [ 16426-64-5 ]
  • [ 17100-65-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 13, p. 3234 - 3237
[2] Patent: US2014/256817, 2014, A1,
  • 7
  • [ 2398-37-0 ]
  • [ 17100-65-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 24, p. 4179 - 4182
[2] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4083 - 4086
  • 8
  • [ 89691-67-8 ]
  • [ 17100-65-1 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 24, p. 4179 - 4182
[2] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4083 - 4086
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