[ CAS No. 123148-66-3 ] {[proInfo.proName]}

Name: 123148-66-3|(2-Methoxypyridin-4-yl)methanol|98%
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SKU: A245874
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Quality Control of [ 123148-66-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 123148-66-3 ]

Product Details of [ 123148-66-3 ]

CAS No. :	123148-66-3	MDL No. :	MFCD00859298
Formula :	C₇H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YENBVKZRNXXJSF-UHFFFAOYSA-N
M.W :	139.15	Pubchem ID :	14462410
Synonyms :

Calculated chemistry of [ 123148-66-3 ]

Physicochemical Properties

Num. heavy atoms :	10
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 :	36.86
TPSA :	42.35 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) :	-6.96 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	0.27
Log Po/w (WLOGP) :	0.43
Log Po/w (MLOGP) :	0.01
Log Po/w (SILICOS-IT) :	1.17
Consensus Log Po/w :	0.73

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.18
Solubility :	9.09 mg/ml ; 0.0653 mol/l
Class :	Very soluble
Log S (Ali) :	-0.72
Solubility :	26.5 mg/ml ; 0.19 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.95
Solubility :	1.55 mg/ml ; 0.0111 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 123148-66-3 ]

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 [ 123148-66-3 ]

* 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 [ 123148-66-3 ]
Downstream synthetic route of [ 123148-66-3 ]

[ 123148-66-3 ] Synthesis Path-Upstream 1~12

1
[ 123148-66-3 ]
[ 72716-87-1 ]

Yield	Reaction Conditions	Operation in experiment
646 mg	With chromium trioxide pyridine In dichloromethane at 20℃; for 2 h;	LiAlH₄ (1.9 g, 49 mmol) was added portionwise to a solution of 2-methoxy isonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0 °C. The reaction mixture was continuously stirred at 0 °C for 1 h, then saturated sodium sulphate solution was added dropwise slowly. After filtration, the filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and concentrated under vacuum. The resulting residue was dissolved in dichloromethane (30 mL), and chromium trioxide pyridine (10.6 g, 49 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, then poured onto the short silica gel column and eluted with ethyl acetate. The resulting solution was concentrated under vacuum to remove the solvent. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 10:1) to afford the title compound (646 mg, 14 percent). ¹H NMR (CDCl₃): δ 10.01 (1H, s), 8.36 (1H, d, J = 5.2 Hz), 7.29 (1H, dd, J = 1.2 Hz, 5.2 Hz), 7.14 (1H, d, J = 1.2 Hz), 3.99 (3H, s).
260 mg	With manganese(IV) oxide In ethyl acetate for 3 h; Reflux	Manganese dioxide (1.04 g) was added to a solution of (2-methoxypyridin-4-yl)methanol (417 mg) in ethyl acetate (5 mL), followed by refluxing for 1.5 hours. Manganese dioxide (1.04 g) was added thereto, followed by refluxing for 1.5 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:6), whereby 2-methoxyisonicotinic aldehyde (260 mg) was obtained as a colorless oily material

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5580 - 5585
[2] Patent: EP2816032, 2014, A1, . Location in patent: Paragraph 0458
[3] Patent: EP2862571, 2015, A1, . Location in patent: Paragraph 0103; 0104
[4] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0942; 0943

2
[ 754218-84-3 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: With hydrogenchloride In ethyl acetate at 0℃; for 0.5 h; Stage #2: With sodium hydrogencarbonate In chloroform; water; ethyl acetate	Reference Example 9 2-Methoxypyridine-4-methanol (Reference compound No.9-1) A solution of 4 N hydrogen chloride in ethyl acetate (11 mL, 44 mmol) was added to 2-methoxypyridine-4-methyl methoxymethyl ether (0.77g, 4.2 mmol, Reference compound No.8-1) under ice-cooling, then the mixture was stirred for 30 minutes. The mixture was diluted with chloroform (100 mL) and washed with a saturated aqueous sodium hydrogencarbonate solution (50 mL) twice. The chloroform layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure to give 0.69 g of the title reference compound as a yellow oil. (Yield 99percent) ¹H-NMR(500MHz,CDCl₃) δ 1.89(s,1H),3.94(s,3H),4.69(d,J = 4.3 Hz,2H),6.75(s,1H),6.85(d,J = 5.2 Hz,1H),8.12(d,J = 5.2 Hz,1H)

Reference： [1] Patent: EP1602647, 2005, A1, . Location in patent: Page/Page column 51

3
[ 26156-51-4 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
33.55 g	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 3 h; Inert atmosphere	To methyl 2-chloroisonicotinate (18, 53.63 g) were added dioxane (150 mL) and sodium methoxide (25.32 g), and the mixture was stirred at reflux temperature for 26 h and then cooled down to room temperature. To the mixture was added acetic acid (28 mL), and the mixture was evaporated in vacuo. To the resulting residue were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried, filtered, and the filtrate was evaporated in vacuo. The resulting residue was dissolved in THF (300 mL). Under an argon atmosphere, the solution was added dropwise to a suspension of lithium aluminum hydride (11.88 g) in THF (500 mL) at 0 °C over 1 h. Then the reaction mixture was stirred at 0 °C for 2 h. To the mixture was added water (30 mL) dropwise at 0 °C, and then THF (270 mL) was added. The mixture was filtered over celite, and the filtrate was evaporated in vacuo to obtain 19 (33.55 g, 75percent) as a orange oil: ¹H NMR (DMSO-d₆) δ 3.83 (3H, s), 4.49 (2H, d, J = 5.3 Hz), 4.70 (1H, t, J = 5.3 Hz), 6.73 (1H, s), 6.90 (1H, d, J = 5.4 Hz), 8.07 (1H, d, J = 5.4 Hz); EI-MS m/z 139 [(M)⁺].

Reference： [1] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5580 - 5585
[2] Patent: WO2011/25851, 2011, A1, . Location in patent: Page/Page column 71
[3] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 582; 583
[4] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5235 - 5246
[5] Patent: EP2816032, 2014, A1, . Location in patent: Paragraph 0457

4
[ 105596-63-2 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: With 4-methyl-morpholine; chloroformic acid ethyl ester In tetrahydrofuran at 0℃; for 0.333333 h; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 20℃; for 16 h;	To a cold (0° C. ice bath) solution of 2-methoxyisonicotinic acid (0.285 g, 1.861 mmol) in anhydrous tetrahydrofuran (10 mL), under nitrogen, was added N-methylmorpholine (0.215 mL, 1.954 mmol) and then ethyl chloroformate (0.187 mL, 1.954 mmol). After stirring for 20 minutes sodium borohydride (0.211 g, 5.58 mmol) was added portionwise. The mixture was cooled (−78° C. dry ice acetone bath) and methanol (10 mL) was added over 5 minutes. The temperature was then allowed to rise to room temperature and stirring was continued for 16 hours. The reaction was poured onto a pad of silica gel, and eluted with dichloromethane until turbid flow stopped, then 10percent methanol in dichloromethane. The later filtrate was concentrated under reduced pressure, and purified by silica gel column chromatography (24 g SiO2, 0-10percent (20CV) methanol in dichloromethane) to afford the product (0.24 g, 1.725 mmol, 93percent yield) as an amber oil. LCMS (Condition ACN-TFA, ES+) M+H=140.1, broad elution, calculated exact mass=139.06. ¹H NMR (400 MHz, CDCl₃) δ: 8.13 (d, J=5.4 Hz, 1H), 6.91-6.83 (m, 1H), 6.76 (s, 1H), 4.70 (d, J=5.6 Hz, 2H), 3.94 (s, 3H), 1.91 (br. s., 1H).

Reference： [1] Patent: US2015/291549, 2015, A1, . Location in patent: Paragraph 1148; 1149
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2669 - 2684
[3] Patent: WO2011/84368, 2011, A1, . Location in patent: Page/Page column 57-58
[4] Patent: EP2862571, 2015, A1, . Location in patent: Paragraph 0103; 0104

5
[ 105596-61-0 ]
[ 123148-66-3 ]

Reference： [1] Patent: US5962458, 1999, A,
[2] Patent: US6362336, 2002, B1, . Location in patent: Example 62

6
[ 100704-10-7 ]
[ 124-41-4 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	for 24 h; Heating / reflux	(2-Methoxy-pyridin-4-yl)-methanol:; (2-Chloro-pyridin-4-yl)-methanol (2.82 g, 19.67 mmol) was refluxed with 25 wt. percent sodium methoxide (25 ml) solution for 24 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1)) to afford 1.8 g (60percent) of (2-Methoxy-pyridin-4-yl)-methanol as a pale brown oil. ¹H NMR (200 MHz, CDCl₃) δ 2.16(3H, s), 2.21 (3H, s), 5.13 (2H, s), 6.99 (1H, d, J=5.6 Hz), 8.11 (1H, br. s), 8.12 (1H, s), 8.23 (1H, d, J=5.6 Hz).

Reference： [1] Patent: US2008/70920, 2008, A1, . Location in patent: Page/Page column 98

7
[ 22282-72-0 ]
[ 123148-66-3 ]

Reference： [1] Patent: WO2011/25851, 2011, A1,

8
[ 58481-11-1 ]
[ 123148-66-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5235 - 5246

9
[ 6313-54-8 ]
[ 123148-66-3 ]

Reference： [1] Patent: EP2816032, 2014, A1,

10
[ 72716-86-0 ]
[ 123148-66-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2669 - 2684

11
[ 33252-30-1 ]
[ 123148-66-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2669 - 2684

12
[ 123148-66-3 ]
[ 120277-15-8 ]

Reference： [1] Patent: WO2012/27261, 2012, A1, . Location in patent: Page/Page column 583; 584
[2] Patent: WO2011/84368, 2011, A1, . Location in patent: Page/Page column 58

[ 123148-66-3 ] Synthesis Path-Downstream 1~79

1
[ 26156-51-4 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium borohydride; In tetrahydrofuran; at 0 - 20℃; for 20h;	To a solution of the above compound (0.425 g, 2.54 mmol) in 2 mL of THF at 0 C under an atmosphere of nitrogen was added lithium borohydride (0.089 g, 4.1 mmol). The mixture was warmed to rt, and after 20 h, filtered and washed with dichloromethane. The organic filtrate was concentrated in vacuo and the residue was purified via silica gel chromatography, eluting with 0- 5% methanol in dichloromethane to provide (2-methoxypyridin-4-yl)methanol that gave proton NMR spectra consistent with theory.
		To a 100-mL round-bottomed flask was added methyl 2- methoxyisonicotinate (2.04 mL, 14.12 mmol, Aldrich, St. Louis, MO) and borane methyl sulfide complex (4.02 mL, 42.4 mmol, Aldrich, St. Louis, MO) in THF (30 mL). The reaction mixture was stirred at 70 C for 18 h, cooled to 0 C and quenched by the addition of MeOH (5 mL), followed by IN NaOH (20 mL). The reaction mixture was extracted with EtOAc (2 x 50 mL), the organic extract was washed with saturated NaCl (20 mL) and dried over Na2S04. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give (2-methoxy-4-pyridinyl)methanol (1.56 g) as colorless oil.
33.55 g	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 3h;Inert atmosphere;	To methyl 2-chloroisonicotinate (18, 53.63 g) were added dioxane (150 mL) and sodium methoxide (25.32 g), and the mixture was stirred at reflux temperature for 26 h and then cooled down to room temperature. To the mixture was added acetic acid (28 mL), and the mixture was evaporated in vacuo. To the resulting residue were added ethyl acetate and water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried, filtered, and the filtrate was evaporated in vacuo. The resulting residue was dissolved in THF (300 mL). Under an argon atmosphere, the solution was added dropwise to a suspension of lithium aluminum hydride (11.88 g) in THF (500 mL) at 0 C over 1 h. Then the reaction mixture was stirred at 0 C for 2 h. To the mixture was added water (30 mL) dropwise at 0 C, and then THF (270 mL) was added. The mixture was filtered over celite, and the filtrate was evaporated in vacuo to obtain 19 (33.55 g, 75%) as a orange oil: 1H NMR (DMSO-d6) delta 3.83 (3H, s), 4.49 (2H, d, J = 5.3 Hz), 4.70 (1H, t, J = 5.3 Hz), 6.73 (1H, s), 6.90 (1H, d, J = 5.4 Hz), 8.07 (1H, d, J = 5.4 Hz); EI-MS m/z 139 [(M)+].

With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at 0℃; for 0.333333h;

B) (2-methoxypyridin-4-yl)methanol To a suspension of lithium aluminum hydride (2.92 g) in diethyl ether (200 mL) and THF (50 mL) was added dropwise a solution of <strong>[26156-51-4]methyl 2-methoxyisonicotinate</strong> (8.57 g) in diethyl ether (50 mL) at 0C, and the reaction mixture was stirred at 0C for 20 min. Water (3.0 mL), 4N aqueous sodium hydroxide solution (3.0 mL) and water (9.0 mL) were successively added to the reaction mixture at 0C, and the mixture was stirred at room temperature for 15 min. The resulting white precipitate was filtered off, and the solvent in the filtrate was evaporated under reduced pressure to give a crude product of the title compound (6.74 g) as a pale-yellow oil.

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5580 - 5585
[2]Patent: WO2011/25851,2011,A1 .Location in patent: Page/Page column 71
[3]Patent: WO2012/27261,2012,A1 .Location in patent: Page/Page column 582; 583
[4]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 5235 - 5246
[5]Patent: EP2816032,2014,A1 .Location in patent: Paragraph 0457

2
[ 123148-66-3 ]
[ 72716-87-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur trioxide pyridine complex; triethylamine; In water; dimethyl sulfoxide; at 10 - 35℃; for 0.5h;	C) 2-methoxyisonicotinaldehyde To a solution of (2-methoxypyridin-4-yl)methanol (6.74 g) and triethylamine (67.5 mL) in DMSO (200 mL) was added sulfur trioxide pyridine complex (30.8 g), and the mixture was stirred at room temperature for 30 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give a crude product of the title compound (4.33 g) as a brown oil.
646 mg	With chromium trioxide pyridine; In dichloromethane; at 20℃; for 2h;	LiAlH4 (1.9 g, 49 mmol) was added portionwise to a solution of 2-methoxy isonicotinic acid (5.0 g, 33 mmol) in tetrahydrofuran (40 mL) at 0 C. The reaction mixture was continuously stirred at 0 C for 1 h, then saturated sodium sulphate solution was added dropwise slowly. After filtration, the filtrate was extracted with ethyl acetate, and the organic layer was washed with brine, and concentrated under vacuum. The resulting residue was dissolved in dichloromethane (30 mL), and chromium trioxide pyridine (10.6 g, 49 mmol) was added. The resulting mixture was stirred at room temperature for 2 h, then poured onto the short silica gel column and eluted with ethyl acetate. The resulting solution was concentrated under vacuum to remove the solvent. The residue was purified by column chromatography (petroleum ether : ethyl acetate = 10:1) to afford the title compound (646 mg, 14 %). 1H NMR (CDCl3): delta 10.01 (1H, s), 8.36 (1H, d, J = 5.2 Hz), 7.29 (1H, dd, J = 1.2 Hz, 5.2 Hz), 7.14 (1H, d, J = 1.2 Hz), 3.99 (3H, s).
260 mg	With manganese(IV) oxide; In ethyl acetate; for 3h;Reflux;	Manganese dioxide (1.04 g) was added to a solution of (2-methoxypyridin-4-yl)methanol (417 mg) in ethyl acetate (5 mL), followed by refluxing for 1.5 hours. Manganese dioxide (1.04 g) was added thereto, followed by refluxing for 1.5 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (hexane:ethyl acetate=9:1?4:6), whereby 2-methoxyisonicotinic aldehyde (260 mg) was obtained as a colorless oily material

Reference： [1]Journal of Organic Chemistry,1989,vol. 54,p. 5580 - 5585
[2]Patent: EP2816032,2014,A1 .Location in patent: Paragraph 0458
[3]Patent: EP2862571,2015,A1 .Location in patent: Paragraph 0103; 0104
[4]Patent: US2016/168139,2016,A1 .Location in patent: Paragraph 0942; 0943

3
[ 123148-66-3 ]
[ 124-63-0 ]
[ 1006300-61-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In chloroform; at 0℃; for 1.1h;	Example X; To a stirred solution of <strong>[123148-66-3](2-Methoxy-pyridin-4-yl)-methanol</strong> (155 mg, 1 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with 6-(3,5-Dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione (20) (286 mg, 1 mmol), powdered anhydrous potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol). DMF (5 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)) to afford 160 mg (38%) of a white solid. m.p. 166-167 C.; 1H-NMR (200 MHz, CDCl3) delta 1.13(3H, d, J=6.7 Hz), 1.22 (3H, d, J=6.7 Hz), 2.26 (1H, m), 3.82 (3H, s), 4.54 (1H, d, J=16.0 Hz), 4.94 (1H, d, J=16.0 Hz), 6.36 (1H, s), 6.56 (1H, d, J=5.3 Hz), 7.23 (1H, s), 7.34 (2H, s), 7.93 (1H, d, J=5.3 Hz), 9.30 (1H, s); m/z (EI) 407(M+); HRMS (EI) Calcd, 407.184662, Found 407.184507.; Example AE; To a stirred solution of <strong>[123148-66-3](2-Methoxy-pyridin-4-yl)-methanol</strong> (155 mg, 1 mmol) in chloroform (10 ml) cooled in an ice bath under nitrogen atmosphere, was added triethylamine (210 mul, 1.5 mmol) and methanesulfonyl chloride (90 mul, 1.2 mmol) was added dropwise. After stirring for 1.1 hr., the reaction mixture was washed with saturated aqueous sodium bicarbonate, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was further dried in high vacuo for ca. 20 min. and mixed with 6-(3-Chloro-5-methyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione (50) (306 mg, 1 mmol), powdered anhydrous potassium carbonate (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol). DMF (5 ml) was then added to the mixture at room temperature and stirred for overnight. After evaporation of DMF, the residue was dissolved in methanol-chloroform (1:9) and filtered through celite pad. The filtrate was then evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:2)) to afford 160 mg (37%) of a white solid. m.p. 98-101 C.; 1H-NMR (200 MHz, CDCl3) delta 1.12(3H, d, J=7.0 Hz), 1.21 (3H, d, J=7.0 Hz), 2.21-2.38 (4H, m), 3.82 (3H, s), 4.47 (1H, d, J=16.0 Hz), 5.05 (1H, d, J=16.0 Hz), 6.34 (1H, s), 6.54 (1H, d, J=5.3 Hz), 7.33 (1H, s), 7.37 (1H, s), 7.52 (1H, s), 7.92 (1H, d, J=5.3 Hz), 8.90 (1H, s); m/z (EI) 427(M+); HRMS (EI) Calcd, 427.129553, Found 427.129884.

Reference： [1]Patent: US2008/70920,2008,A1 .Location in patent: Page/Page column 50; 52; 54-55

4
[ 100704-10-7 ]
[ 124-41-4 ]
[ 123148-66-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	for 24h;Heating / reflux;	(2-Methoxy-pyridin-4-yl)-methanol:; (2-Chloro-pyridin-4-yl)-methanol (2.82 g, 19.67 mmol) was refluxed with 25 wt. % sodium methoxide (25 ml) solution for 24 hr. After cooling to room temperature, the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, EA:hexane (1:1)) to afford 1.8 g (60%) of (2-Methoxy-pyridin-4-yl)-methanol as a pale brown oil. 1H NMR (200 MHz, CDCl3) delta 2.16(3H, s), 2.21 (3H, s), 5.13 (2H, s), 6.99 (1H, d, J=5.6 Hz), 8.11 (1H, br. s), 8.12 (1H, s), 8.23 (1H, d, J=5.6 Hz).

Reference： [1]Patent: US2008/70920,2008,A1 .Location in patent: Page/Page column 98

5
[ 123148-66-3 ]
[ 123148-70-9 ]