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[ CAS No. 171366-19-1 ] {[proInfo.proName]}

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Chemical Structure| 171366-19-1
Chemical Structure| 171366-19-1
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Product Details of [ 171366-19-1 ]

CAS No. :171366-19-1 MDL No. :MFCD03095295
Formula : C6H5FINO Boiling Point : -
Linear Structure Formula :- InChI Key :FQCZQIGAGKWNEA-UHFFFAOYSA-N
M.W : 253.01 Pubchem ID :11021396
Synonyms :

Calculated chemistry of [ 171366-19-1 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.04
TPSA : 33.12 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) : -7.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : 1.05
Log Po/w (WLOGP) : 1.59
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 2.59
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.45
Solubility : 0.901 mg/ml ; 0.00356 mol/l
Class : Soluble
Log S (Ali) : -1.34
Solubility : 11.7 mg/ml ; 0.0461 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.09
Solubility : 0.206 mg/ml ; 0.000815 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 1.83

Safety of [ 171366-19-1 ]

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 [ 171366-19-1 ]

* 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 [ 171366-19-1 ]
  • Downstream synthetic route of [ 171366-19-1 ]

[ 171366-19-1 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 153034-82-3 ]
  • [ 171366-19-1 ]
Reference: [1] Patent: WO2012/75383, 2012, A2, . Location in patent: Page/Page column 123
  • 2
  • [ 113975-22-7 ]
  • [ 109-94-4 ]
  • [ 171366-19-1 ]
YieldReaction ConditionsOperation in experiment
62 % With n-butyllithium; sodium borohydrid; diisopropylamine In tetrahydrofuran; ethyl acetate EXAMPLE 1
2-Fluoro-4-iodo-3-(hydroxymethyl)pyridine
To a solution of LDA, freshly prepared from diisopropylamine (0.63 mL, 4.49 mmol) and n-BuLi (4.49 mmol) in THF (10 mL) at -78° C., is cannulated a solution of 2-fluoro-3-iodopyridine (1 g, 4.48 mmol) in 2 mL of THF, and the mixture is stirred for 1 hour at -78° C. under nitrogen.
Ethyl formate (1.1 mL, 13.6 mmol) is added to the reaction mixture at -78° C. and stirring is continued for 30 min.
The reaction is quenched with saturated sodium bicarbonate solution at -78° C. and allowed to warm to room temperature.
Sodium borohydride (0.34 g, 8.99 mmol) is slowly added to the reaction mixture and then stirred for 30 min.
The mixture is extracted with ethyl acetate.
The combined ethyl acetate extracts are washed with brine, dried (MgSO4) and concentrated in vacuo.
The residue is purified by radial plc (silica gel, hexanes, 10percent EtOAc/hexanes,
20percent EtOAc/hexanes) to afford 708 mg (62 percent) of the product as a white solid having a mp of 69°-70° C.
Elemental Analysis for C6 H5 FINO: theory: C 28.48, H 1.99, N 5.54; found: C 28.55, H 1.94, N 5.48. IR (KBr): cm1 3336, 1584, 1541, 1446, 1401, 1264, 1218, 1003, 870, 833,803,761,577. 1 H NMR (CDCl3): δ7.79-7.82 (d, 1H,J=5 Hz), 7.66-7.68 (d, 1H, J=5 Hz), 4.82-4.86 (d, 2H, J=7 Hz), 1.99-2.04 (t, 1H, J=14 Hz).
13 C NMR (CDCl3): δ 162.29, 159.05, 147.30, 147.09, 132.79, 132.73,126.14, 125.73, 114.21, 62.24.
Reference: [1] Patent: US5496952, 1996, A,
  • 3
  • [ 853798-93-3 ]
  • [ 171366-19-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 44, p. 7995 - 7998
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