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[ CAS No. 623942-84-7 ] {[proInfo.proName]}

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Chemical Structure| 623942-84-7
Chemical Structure| 623942-84-7
Structure of 623942-84-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 623942-84-7 ]

CAS No. :623942-84-7 MDL No. :MFCD12406110
Formula : C7H8BrNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FNRPOELSJDDLSG-UHFFFAOYSA-N
M.W : 218.05 Pubchem ID :11769918
Synonyms :

Calculated chemistry of [ 623942-84-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.56
TPSA : 42.35 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) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.14
Log Po/w (XLOGP3) : 1.0
Log Po/w (WLOGP) : 1.19
Log Po/w (MLOGP) : 0.77
Log Po/w (SILICOS-IT) : 1.85
Consensus Log Po/w : 1.39

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.09
Solubility : 1.76 mg/ml ; 0.00806 mol/l
Class : Soluble
Log S (Ali) : -1.48
Solubility : 7.25 mg/ml ; 0.0332 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.314 mg/ml ; 0.00144 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.97

Safety of [ 623942-84-7 ]

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 [ 623942-84-7 ]

* 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 [ 623942-84-7 ]
  • Downstream synthetic route of [ 623942-84-7 ]

[ 623942-84-7 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 623942-84-7 ]
  • [ 269058-49-3 ]
YieldReaction ConditionsOperation in experiment
80% With manganese(IV) oxide In chloroform for 18 h; Heating / reflux Step F.
3-Bromo-6-methoxy-pyridine-2-carbaldehyde.
A mixture of (3-bromo-6-methoxy-pyridin-2-yl)-methanol (3.25 g, 14.9 mmol) and MnO2 (9.07 g, 104 mmol) in CHCl3 (50 mL) was heated at reflux for 18 h.
The mixture was filtered while hot and the filtrate was concentrated.
The residue was purified (SiO2; 10percent EtOAc/hexanes) to yield the title compound (2.55 g, 80percent). MS (ESI): mass calcd. for C7H6BrNO2, 214.96; m/z found, 218.2 [M+H]+. 1H NMR (CDCl3): 10.13 (s, 1H), 7.80 (d, J=8.7, 1H), 6.83 (d, J=8.7, 1H), 3.99 (s, 3H).
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 12, p. 2007 - 2009
[2] Organic and Biomolecular Chemistry, 2003, vol. 1, # 16, p. 2865 - 2876
[3] Patent: US2006/287292, 2006, A1, . Location in patent: Page/Page column 29
[4] Patent: US2016/75711, 2016, A1, . Location in patent: Paragraph 0570; 0574
  • 2
  • [ 269058-51-7 ]
  • [ 623942-84-7 ]
YieldReaction ConditionsOperation in experiment
90% at 20℃; for 18 h; Step E.
(3-Bromo-6-methoxy-pyridin-2-yl)-methanol.
A mixture of acetic acid 3-bromo-6-methoxy-pyridine-2-ylmethyl ester (3.94 g, 15.2 mmol) and 1 M aq. K2CO3 (26.2 mL, 26.2 mmol) in MeOH (30 mL) was stirred at rt for 18 h.
The mixture was concentrated, diluted with H2O (15 mL), and extracted with DCM (3*).
The combined extracts were washed with H2O, dried, and concentrated to give the title compound (2.97 g, 90percent). MS (ESI): mass calcd. for C7H8BrNO2, 216.97; m/z found, 218.2 [M+H]+. 1H NMR (CDCl3): 7.68 (d, J=8.6, 1H), 6.60 (d, J=8.6, 1H), 4.67 (dd, J=4.7, 0.6, 2H), 4.01 (t, 4.7, 1H), 3.97 (s, 3H).
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 12, p. 2007 - 2009
[2] Organic and Biomolecular Chemistry, 2003, vol. 1, # 16, p. 2865 - 2876
[3] Patent: US2006/287292, 2006, A1, . Location in patent: Page/Page column 29
[4] Patent: US2016/75711, 2016, A1, . Location in patent: Paragraph 0570; 0573
  • 3
  • [ 63071-12-5 ]
  • [ 623942-84-7 ]
Reference: [1] Patent: WO2011/28395, 2011, A1, . Location in patent: Page/Page column 20-21
  • 4
  • [ 126717-59-7 ]
  • [ 108-24-7 ]
  • [ 623942-84-7 ]
YieldReaction ConditionsOperation in experiment
1.75 g
Stage #1: With 3-chloro-benzenecarboperoxoic acid In chloroform at 0 - 20℃; for 24 h;
Stage #2: at 120℃; for 3 h;
Stage #3: With potassium carbonate In methanol; water at 20℃; for 1 h;
To a solution of 3-bromo-6-methoxy-2-methylpyridine (CAS No. 126717-59-7) (5.5 g, 27.2 mmol, 1 equivalent) in chloroform (100 mL) was added 65percent mCPBA (10.8 g, 40.8 mmol, 1.5 equivalents) at 0° C.
The reaction mixture was warmed up to room temperature and stirred for 24 hours.
To the reaction mixture were added an aqueous sodium thiosulfate pentahydrate solution and a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with chloroform.
The resulting organic layer was dried over magnesium sulfate, filtered, and then concentrated under reduced pressure.
The residue was purified with silica gel column chromatography (silica gel, 0percent-20percent methanol/ethyl acetate).
The resulting compound was stirred in acetic anhydride (20 mL) at 120° C. for 3 hours.
To the reaction mixture was added methanol, and the mixture was concentrated under reduced pressure.
To the residue was added water, and the mixture was extracted with ethyl acetate.
The combined organic layers were washed with a saturated aqueous sodium chloride solution.
The organic layers were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure.
The resulting residue was purified with silica gel column chromatography (silica gel, 20percent-75percent ethyl acetate/n-heptane).
To the resulting compound in methanol (22 mL) was added potassium carbonate (1 M aqueous solution, 10.4 mL) at room temperature.
After stirring at the same temperature for 1 hour, the reaction mixture was concentrated under reduced pressure.
To the residue was added water, and the mixture was extracted with chloroform.
The combined organic layers were washed with a saturated aqueous sodium chloride solution.
The organic layers were dried over magnesium sulfate, filtered, and then concentrated under reduced pressure to afford the title compound (1.75 g).
1H-NMR (400 MHz, CDCl3) δ (ppm): 3.97 (s, 3H), 4.03 (t, J=4.7 Hz, 1H), 4.68 (dd, J=4.7, 0.8 Hz, 2H), 6.57-6.64 (m, 1H), 7.69 (d, J=8.6 Hz, 1H).
Reference: [1] Patent: US2017/137436, 2017, A1, . Location in patent: Paragraph 0203-0205
  • 5
  • [ 126717-59-7 ]
  • [ 623942-84-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 16, p. 2865 - 2876
[2] Tetrahedron Letters, 2000, vol. 41, # 12, p. 2007 - 2009
[3] Patent: US2016/75711, 2016, A1,
  • 6
  • [ 269058-50-6 ]
  • [ 623942-84-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2003, vol. 1, # 16, p. 2865 - 2876
[2] Tetrahedron Letters, 2000, vol. 41, # 12, p. 2007 - 2009
[3] Patent: US2016/75711, 2016, A1,
  • 7
  • [ 40473-07-2 ]
  • [ 623942-84-7 ]
Reference: [1] Patent: WO2011/28395, 2011, A1,
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