[ CAS No. 1547-29-1 ] {[proInfo.proName]}

Name: 1547-29-1|3-Fluoro-2-hydroxypyridine|98%
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SKU: A113907
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Quality Control of [ 1547-29-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1547-29-1 ]

CAS No. :	1547-29-1	MDL No. :	MFCD03095042
Formula :	C₅H₄FNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CISUDJRBCKKAGX-UHFFFAOYSA-N
M.W :	113.09	Pubchem ID :	2783363
Synonyms :

Calculated chemistry of [ 1547-29-1 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	26.22
TPSA :	33.12 Å²

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) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	0.93
Log Po/w (WLOGP) :	1.35
Log Po/w (MLOGP) :	0.62
Log Po/w (SILICOS-IT) :	1.39
Consensus Log Po/w :	1.04

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.68
Solubility :	2.35 mg/ml ; 0.0208 mol/l
Class :	Very soluble
Log S (Ali) :	-1.21
Solubility :	6.94 mg/ml ; 0.0614 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.67
Solubility :	2.42 mg/ml ; 0.0214 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 1547-29-1 ]

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 [ 1547-29-1 ]

* 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 [ 1547-29-1 ]
Downstream synthetic route of [ 1547-29-1 ]

[ 1547-29-1 ] Synthesis Path-Upstream 1~2

1
[ 2267-37-0 ]
[ 1547-29-1 ]

Reference： [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1616

2
[ 1547-29-1 ]
[ 1079179-12-6 ]

Reference： [1] MedChemComm, 2016, vol. 7, # 5, p. 1022 - 1032

[ 1547-29-1 ] Synthesis Path-Downstream 1~53

1
[ 2267-37-0 ]
[ 1547-29-1 ]

Reference： [1]Journal of Organic Chemistry,1958,vol. 23,p. 1616

2
[ 1547-29-1 ]
[ 873009-38-2 ]
5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; phosphate potassium salt; N,N`-dimethylethylenediamine; In 1,4-dioxane; dimethyl sulfoxide; at 120℃;	EXAMPLE 291; 5-Chloro-N-(( 1 -(4-(3 -fluoro-2-oxopyridin- 1 (2H)-yl)phenyl)- 1 H- 1 ,2,3 -triazol-4- yl)methyl)thiophene-2-carboxamide; [0814] Aryl iodide 35 (Example 290, 50 mg, 0.11 mmol) and <strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong> (38 mg, 0.33 mmol) were dissolved in 1.0 mL dry dioxane and 0.3 mL dry DMSO in a sealed tube. To it were added N,N'-dimethylethylenediamine (8 muL, 0.066 mmol), CuI (11 mg, 0.055 mmol) and K3PO4 (48 mg, 0.22 mmol) in order. The mixture was stirred and heated in 1200C bath for overnight. The mixture was filtered and directly subjected to reverse phase preparative HPLC to isolate the title compound as a white powder after lyophilization. MS found for C19Hi3ClFN5O2S as (M+H)+ 430.0, 432.0.

Reference： [1]Patent: WO2006/2099,2006,A2 .Location in patent: Page/Page column 184

3
[ 1547-29-1 ]
[ 945559-61-5 ]
5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 8-quinolinol; potassium carbonate;copper(l) iodide; In dimethyl sulfoxide; at 130℃;	Example 32 5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (43) A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-6 (66 mg, 0.15 mmol), <strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong> (46 mg, 0.40 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (50 mg, 0.36 mmol) in DMSO (1 mL) was degassed with Ar before being charged with CuI (15 mg, 0.079 mmol). The mixture in a sealed tube, was heated at 130 C. overnight. The mixture was then purified by HPLC to give the titled compound (8 mg). MS 429.0 and 431.0 (M+H, Cl pattern).

Reference： [1]Patent: US2007/259924,2007,A1 .Location in patent: Page/Page column 35

4
[ 1547-29-1 ]
[ 955133-31-0 ]
5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-2-(methylsulfinyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide [ No CAS ]
5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-2-(methylsulfonyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5-chloro-N-((1-(4-(3-fluoro-2-oxopyridin-1(2H)-yl)phenyl)-2-(methylsulfonyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (67) A mixture of 5-chloro-N-((1-(4-iodophenyl)-2-(methylthio)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide (50 mg, 0.10 mmol), <strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong> (30 mg, 0.26 mmol), 8-hydroxyquinoline (10 mg, 0.069 mmol) and K2CO3 (70 mg, 0.50 mmol) in DMSO (2 mL) was degassed with Ar before being charged with CuI (28 mg, 0.15 mmol). The mixture in a sealed tube was heated at 130 C. overnight. After being cooled down to room temperature, H2O (5 mL) was added to induce precipitation, which was collected and dried on vacuum to give a solid (34 mg). To a solution of the solid (34 mg, 0.072 mmol) in DMF (4 mL), a solution of oxone (200 mg, 0.65 mmol) in H2O (3 mL) was added. The mixture was stirred at room temperature overnight. It was then purified by HPLC to give both the sulfone (2 mg) and sulfoxide (4 mg) products. MS 507.0 and 509.0 (M+H, Cl pattern, for sulfone); 491.0 and 493.0 (M+H, Cl pattern, for sulfoxide).

Reference： [1]Patent: US2007/259924,2007,A1 .Location in patent: Page/Page column 43

5
[ 1547-29-1 ]
Na₂ SO₃ [ No CAS ]
5-bromo-3-fluoro-2-hydroxypyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In N-methyl-acetamide; water;	EXAMPLE 5 3-fluoro-2-octyloxy-5-(4-octyloxyphenyl)pyridine 32.0 ml (620.0 mmol) of bromine are added dropwise at 0 C. to 63.7 g (563.2 mmol) of <strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong> in 700 ml of dimethylformamide. After the mixture has been stirred at room temperature for a further two hours, 800 ml of water are added, and 78 g of Na2 SO3 in 350 ml of water are added dropwise. The mixture is then extracted three times with 400 ml of dichloromethane in each case, and the organic phase is dried over Na2 SO4 and evaporated to dryness, giving 97.6 g of 5-bromo-<strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong>. STR21

Reference： [1]Patent: US5445763,1995,A

6
[ 1547-29-1 ]
[ 1191454-81-5 ]
[ 1191454-84-8 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 4h;	A solution of 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (0.38 g, 1 mmol) in N,N-dimethylformamide (10 mL) was treated with <strong>[1547-29-1]3-fluoro-pyridin-2-ol</strong> (0.15 g, 1 mmol) and potassium carbonate (0.16 g, 1.2 mmol). The reaction was heated at 120 C. for 4 h and then concentrated in vacuo. The residue was partitioned between water and methylene chloride. The aqueous layer was back extracted with methylene chloride. The combined organics were washed with a saturated aqueous sodium chloride solution, and then concentrated in vacuo. Chromatography (1/1 ethyl acetate/petroleum ether) afforded 3-cyclopentyl-2-[4-(3-fluoro-pyridin-2-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester (0.19 g, 53%).

Reference： [1]Patent: US2009/264434,2009,A1 .Location in patent: Page/Page column 65

7
[ 1547-29-1 ]
[ 141699-59-4 ]
[ 1189550-34-2 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 75℃;	t-Butyl 4-(methanesulfonyloxy)piperidine-1-carboxylate (2.96 g, 10.6 mmol) and potassium carbonate (2.69 g, 19.5 mmol) were added to a N,N-dimethylformamide solution (45 ml) of <strong>[1547-29-1]3-fluoro-2-hydroxypyridine</strong> (1.00 g, 8.84 mmol), at room temperature, and stirring was carried out at 75C overnight. The reaction solution was cooled to room temperature, and water was added to the residue resulting from concentration, followed by extraction with methylene chloride. After the resulting organic layer was dried over anhydrous sodium sulfate, the residue resulting from concentration was purified by silica gel column chromatography to afford t-butyl 4-[(3-fluoropyridin-2-yl)oxy]piperidine-1-carboxylate (1.63 g, yield 62%) as a colorless oil. 1H-NMR (CDCl3, 400 MHz) delta: 7.88 (1H, d, J=3.9 Hz), 7.33-7.29 (1H, m), 6.84-6.81 (1H, m), 5.32-5.27 (1H, m), 3.81-3.77 (2H, m), 3.33-3.28 (2H, m), 2.02-1.98 (2H, m), 1.82-1.75 (2H, m), 1.47 (9H, s). MS (ESI, m/z): 241 (M-tBu+H)+.

Reference： [1]Patent: EP2258697,2010,A1 .Location in patent: Page/Page column 65

8
[ 1547-29-1 ]
[ 572-09-8 ]
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(3-fluoropyridin-2-yloxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate [ No CAS ]

Reference： [1]Molecules,2013,vol. 18,p. 3789 - 3805

9
[ 1547-29-1 ]
[ 1354894-94-2 ]
2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-(3-fluoro-2-oxopyridin-1(2H)-yl)-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20 mg	With salicylaldehyde-oxime; caesium carbonate; copper(II) oxide; In acetonitrile; at 200℃; for 1h;Microwave irradiation; Inert atmosphere;	Example 24 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-(3-fluoro-2-oxopyridin-1(2H)-yl)-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one Under argon atmosphere, 200 mg (purity 62%, 0.24 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one (example 15A) was suspended in 2.5 ml of absolute acetonitrile, and 545 mg (4.82 mmol) of <strong>[1547-29-1]3-fluoropyridin-2-ol</strong>, 157 mg (0.48 mmol) of caesium carbonate, 7 mg (0.05 mmol) of copper(I) oxide and 20 mg (0.15 mmol) of 2-hydroxybenzaldehyde-oxime were added. The mixture was heated in the microwave for 1 h at 200 C. The reaction solution was filtered and purified by preparative HPLC (eluent: acetonitrile/water, gradient 20:80?100:0). 20 mg (23% of theor.) of the target compound was obtained. LC-MS (method 1): Rt=1.11 min; MS (ESIpos): m/z=500 [M+H]+ 1H-NMR (400 MHz, DMSO-d6): delta [ppm]=1.49 (s, 6H), 5.81 (s, 2H), 7.10-7.23 (m, 4H), 7.32-7.38 (m, 1H), 7.61-7.65 (m, 2H), 8.07-8.12 (m, 1H), 8.36 (dd, 1H), 8.59 (dd, 1H), 11.75 (s, 1H).

Reference： [1]Patent: US2013/338137,2013,A1 .Location in patent: Paragraph 1790; 1791; 1792; 1793

10
[ 120277-69-2 ]
[ 1547-29-1 ]
1-(5-bromopyridin-3-ylmethyl)-3-fluoro-1-pyridin-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 6h;	General procedure: To a solution of <strong>[120277-69-2]3-bromo-5-chloromethyl-pyridine</strong> (0.05 g, 0.242 mmol) in DMF (1 mL) were added 6-chloro-lH-pyridin-2-one (0.031 g, 0.242 mmol) and K2C03 (0.067 g, 0.484 mmol) and the reaction mixture was stirred at room temperature for 6 h. The mixture was diluted with EtOAc, poured into H20 (3 mL) and the aqueous layer was extracted with EtOAc (2 x 10 mL). Combined organics were dried over Na2S04, filtered and evaporated. The residue was purified by silica gel flash chromatography eluting with a 0 to 100% EtO Ac-heptane gradient to give 2- ((5-bromopyridin-3-yl)methoxy)-6-chloropyridine (0.05 g, 69 %) as a colorless liquid, MS: 301.3 (M+H+); and l-(5-bromo-pyridin-3-ylmethyl)-6-chloro-lH-pyridin-2-one (0.011 g, 15 %) as a yellow solid. MS: 301.3 (M+H+). The following intermediates listed in Table 1 were prepared from 3-bromo-5-chloromethyl- pyridine (intermediate A-2 [A]), in analogy to the procedure described for the preparation of intermediates A-2 [B], using appropriate reaction partners.

Reference： [1]Patent: WO2014/139981,2014,A1 .Location in patent: Page/Page column 25; 26; 30

11
[ 1547-29-1 ]
[ 456-04-2 ]
C₁₃H₉F₂NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate; In acetone; for 1h;Reflux;	Step 1 [0251] Acetone (6.3 mL) was added to <strong>[1547-29-1]3-fluoropyridin-2-ol</strong> (V-2) (300 mg, 3.15 mmol) and potassium carbonate (1.13 g, 3.47 mmol), and then 2-chloro-1-(4-fluorophenyl)ethanone (II-37) (691 mg, 3.47 mmol) was added, and the resultant mixture was heated under reflux for 1 hour. The reaction solution was filtered, and then the solvent was removed under reduced pressure. The resultant product was purified by silica gel column chromatography to obtain compound (IV-49) (amount 395 mg, yield 90%).
90%	With caesium carbonate; In acetone; for 1h;Reflux;	Step 1 Acetone (6.3 mL) was added to <strong>[1547-29-1]3-fluoropyridin-2-ol</strong> (V-2) (300 mg, 3.15 mmol) and cesium carbonate (1.13 g, 3.47 mmol), and then 2-chloro-1-(4-fluorophenyl)ethanone (II-37) (691 mg, 3.47 mmol) was added, and the resultant mixture was heated under reflux for 1 hour. The reaction solution was filtered, and then the solvent was removed under reduced pressure. The resultant product was purified by silica gel column chromatography to obtain compound (IV-49) (amount 395 mg, yield 90%).

Reference： [1]Patent: EP2789607,2014,A1 .Location in patent: Paragraph 0250-0251
[2]Patent: US2016/168540,2016,A1 .Location in patent: Paragraph 0419

12
[ 1547-29-1 ]
[ 135-73-9 ]
5-([1,1'-biphenyl]-4-yl)-5-[(3-fluoro-2-oxopyridin-1(2H)-yl)methyl]imidazolidine-2,4-dione [ No CAS ]

Reference： [1]Patent: EP2789607,2014,A1
[2]Patent: US2016/168540,2016,A1

13
[ 1547-29-1 ]
[ 135-73-9 ]
C₁₉H₁₄FNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.25h;	Step 1 [0254] Dimethyl sulfoxide (3.6 mL) was added to compound (V-2) (226 mg, 2.00 mmol) and potassium carbonate (628 mg, 4.54 mmol), and then 1-([1,1'-biphenyl]-4-yl)-2-bromoethanone (II-38) (500 g, 1.87 mmol) was added, and the resultant mixture was stirred for 1.25 hours at room temperature. Water was added to the reaction solution and the precipitated solid was collected by filtration to obtain compound (IV-50) (amount 665 mg, quantitative yield).
100%	With potassium carbonate; In dimethyl sulfoxide; at 20℃; for 1.25h;	Dimethyl sulfoxide (3.6 mL) was added to compound (V-2) (226 mg, 2.00 mmol) and potassium carbonate (628 mg, 4.54 mmol), and then 1-([1,1?-biphenyl]-4-yl)-2-bromoethanone (II-38) (500 mg, 1.87 mmol) was added, and the resultant mixture was stirred for 1.25 hours at room temperature. Water was added to the reaction solution and the precipitated solid was collected by filtration to obtain compound (IV-50) (amount 665 mg, quantitative yield).

Reference： [1]Patent: EP2789607,2014,A1 .Location in patent: Paragraph 0253-0254
[2]Patent: US2016/168540,2016,A1 .Location in patent: Paragraph 0424

14
[ 109-04-6 ]
[ 1547-29-1 ]
11-benzoyl-3-fluoroimidazo[1,2-a:3,4-a′]dipyridin-5-ium-4-olate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 1064 - 1067

15
[ 109-04-6 ]
[ 1547-29-1 ]
3-fluoro-2H-[1,2'-bipyridin]-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine; In toluene; at 120℃; for 2h;Inert atmosphere;	General procedure: Following a reported procedure,1 copper iodide (5 mol %), potassium phosphate tribasic (2.00 equiv), the corresponding 2-hydroxypyridine (1.00 equiv) and the corresponding 2-bromopyridine (2.00 equiv) were suspended in toluene [0.4 M] under N2. N,N?-Dimethylethylenediamine (0.10 equiv) was added and the resulting mixture was stirred 20 h at 120 C. The resulting mixture was allowed to cool to rt and then quenched with water. A small amount of N,N?-dimethylethylenediamine was added to dissolve the residual copper salts into the aqueous phase. The layers were separated and the aqueous layer was extracted three times with EtOAc (20 mL). The organic layers were combined, dried over MgSO4 and concentrated under reduced pressure. A purification by flash chromatography (eluent DCM/EtOAc 1:1 with 4%vv of NEt3) affordeded the desired product.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 1208 - 1214
[2]Organic Letters,2016,vol. 18,p. 1064 - 1067

16
[ 1547-29-1 ]
2-((3-fluoro-5-nitropyridin-2-yl)oxy)-N,N-dimethylethan-1-amine [ No CAS ]