[ CAS No. 84547-61-5 ] {[proInfo.proName]}

Name: 84547-61-5|(1-Methyl-1H-pyrazol-5-yl)methanol|98%
Brand: Ambeed
SKU: A237158
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Quality Control of [ 84547-61-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 84547-61-5 ]

Product Details of [ 84547-61-5 ]

CAS No. :	84547-61-5	MDL No. :	MFCD08556301
Formula :	C₅H₈N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WQFOGLYQVFBDEY-UHFFFAOYSA-N
M.W :	112.13	Pubchem ID :	11815316
Synonyms :

Calculated chemistry of [ 84547-61-5 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.62
TPSA :	38.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.94
Log Po/w (XLOGP3) :	-0.62
Log Po/w (WLOGP) :	-0.24
Log Po/w (MLOGP) :	-0.53
Log Po/w (SILICOS-IT) :	0.19
Consensus Log Po/w :	-0.05

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.54
Solubility :	32.3 mg/ml ; 0.288 mol/l
Class :	Very soluble
Log S (Ali) :	0.29
Solubility :	220.0 mg/ml ; 1.96 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.57
Solubility :	30.4 mg/ml ; 0.271 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.32

Safety of [ 84547-61-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 84547-61-5 ]

* 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 [ 84547-61-5 ]
Downstream synthetic route of [ 84547-61-5 ]

[ 84547-61-5 ] Synthesis Path-Upstream 1~6

1
[ 16034-46-1 ]
[ 84547-61-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2 h; Inert atmosphere	To a solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) in tetrahydrofuran (50 mL) was added L1AIH₄ (720 mg, 18.97 mmol) in portions at 0 °C under an inert atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature then quenched by the addition of water (2 mL). The mixture was dried over by anhydrous sodium sulfate and the solids were filtered out. The filtrates were concentrated under reduced pressure to afford (1 -methyl- lH-pyrazol- 5-yl)methanol as colorless oil (1.2 g, 67 ). (ES, m/z) [M+H]⁺ 113.0 *H NMR (300 MHz, CDC1₃) δ 7.36 (d, 7 = 1.8 Hz, 1H), 6.18 (d, 7 = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H)

Reference： [1] Patent: WO2014/66795, 2014, A1, . Location in patent: Paragraph 0175
[2] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2297 - 2303[3] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2598 - 2605
[4] Patent: WO2014/151142, 2014, A1,
[5] Patent: WO2016/29454, 2016, A1, . Location in patent: Page/Page column 64

2
[ 17827-60-0 ]
[ 84547-61-5 ]

Yield	Reaction Conditions	Operation in experiment
83.3%	With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 12 h;	To a stirred solution of methyl l-methyl-lH-pyrazole-5-carboxylate (3 g, 21.4 mmol) in tetrahydrofuran (50 mL) at 0 °C was added lithium aluminum hydride (977 mg, 25.7 mmol). The mixture was stirred at room temperature for 12 h. The reaction was quenched by adding water, extracted with ethyl acetate (100 mL), dried, concentrated and the residue was purified by column chromatography on silica gel (petroleum ether/ acetic ester =10: 1), to afford the title compound as an off-white oil (2 g, 83.3percent).

Reference： [1] Patent: WO2014/151142, 2014, A1, . Location in patent: Paragraph 0093

3
[ 27258-33-9 ]
[ 84547-61-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 2, p. 363 - 386
[2] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 11, p. 1409 - 1414
[3] Patent: EP1422228, 2004, A1, . Location in patent: Page 221-222
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 10, p. 1099 - 1104
[5] Patent: WO2008/125600, 2008, A2, . Location in patent: Page/Page column 30

4
[ 930-36-9 ]
[ 68-12-2 ]
[ 84547-61-5 ]
[ 84547-62-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 961 - 982

5
[ 84547-59-1 ]
[ 84547-61-5 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1982, vol. 52, # 11, p. 2297 - 2303[2] Zhurnal Obshchei Khimii, 1982, vol. 52, # 11, p. 2598 - 2605

6
[ 930-36-9 ]
[ 68-12-2 ]
[ 84547-61-5 ]
[ 84547-62-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 4, p. 961 - 982

[ 84547-61-5 ] Synthesis Path-Downstream 1~56

1
[ 84547-59-1 ]
[ 84547-61-5 ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

2
[ 84547-61-5 ]
5-(chloromethyl)-1-methyl-1H-pyrazole hydrochloride [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

3
[ 18162-48-6 ]
[ 84547-61-5 ]
[ 351529-85-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

4
[ 27258-33-9 ]
[ 84547-61-5 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of aluminum lithium hydride (691 mg) in THF (10 ml), a solution of 1-methylpyrazole-5-carboxyaldehyde (2.0 g) in THF (20 ml) was added dropwise at 0C under nitrogen atmosphere. After finishing the dropping, water (0.7 ml), 15% aqueous solution of sodium hydroxide (0.7 ml) and water (2.1 ml) were sequentially added to the mixture at 0C, and the mixture was stirred for 2 hours at room temperature. The mixture was dried over magnesium sulfate, and the insolubles were filtered off. The solvent was distilled off under reduced pressure, to give 5-hydroxymethyl-1-methylpyrazole (2.04 g) as colorless oil. 1H-NMR (200 MHz, CDCl3) delta 3.90 (3H, s), 4.68 (2H, s), 6.19 (1H, d, J = 2.0 Hz), 6.39 (1H, d, J = 1.8 Hz)
		(ii) (1-Methyl-1 H-pyrazol-5-yl)methanol was prepared as follows (c.f. Bioorg. Med. Chem., 2001 , 9, 961-982): A stirred solution of 1-methyl-1 H-pyrazole-5- carbaldehyde (5.2 g, 47 mmol) in ethanol (50 ml) at 5C was treated with sodium borohydride (893 mg, 23. 5mmol). The reaction mixture was stirred at 5C for 30 minutes, hydrochloric acid (5N, 10 ml) was added and the organic solvent was evaporated. The residue was partitioned between ethyl acetate and water. The layers were separated and the aqueous solution was saturated with sodium chloride and re-extracted with ethyl acetate. The combined organic extracts were washed with brine, then dried and evaporated to afford (1-methyl-1 H-pyrazol-5-yl)methanol which was used in the next step.

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 363 - 386
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414
[3]Patent: EP1422228,2004,A1 .Location in patent: Page 221-222
[4]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 1099 - 1104
[5]Patent: WO2008/125600,2008,A2 .Location in patent: Page/Page column 30

5
[ 84547-61-5 ]
[ 1193-02-8 ]
[ 497855-73-9 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of <strong>[84547-61-5]5-hydroxymethyl-1-methylpyrazole</strong> (645 mg) in chloroform (10 ml) was added one droplet of DMF, and thionyl chloride (0.55 ml) was added to the mixture at 0C. The mixture was allowed to be at room temperature under nitrogen atmosphere, and the mixture was stirred for 40 hours. The solvent was distilled off under reduced pressure and the obtained residue was dissolved in methanol (10 ml). This solution was added to a mixed solution of 4-aminothiophenol (600 mg) and sodium hydroxide (460 mg) in methanol (10 ml) and water (6 ml) at 0C. The mixture was allowed to be at room temperature and stirred for 30 minutes, and water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was recrystallized from hexane-ethyl acetate, to give 4-[[(1-methylpyrazol-5-yl)methyl]sulfanyl]aniline (972 mg) as brown crystals. 1H-NMR (200 MHz, CDCl3) delta 3.75 (3H, s), 3.89 (2H, s), 5.92 (1H, d, J = 1.8 Hz), 6.57 (2H, d, J = 8.8 Hz), 7.10 (2H, d, J = 8.8 Hz), 7.31 (1H, d, J = 1.8 Hz). Elemental Analysis C11H13N3S Calcd. C, 60.24; H, 5.97; N, 19.16; Found. C, 60.09; H, 6.08; N, 19.11.

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 363 - 386
[2]Patent: EP1422228,2004,A1 .Location in patent: Page 222

6
[ 930-36-9 ]
[ 68-12-2 ]
[ 84547-61-5 ]
[ 84547-62-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

7
[ 84547-61-5 ]
[ 164162-14-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

8
[ 84547-61-5 ]
[ 164162-16-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

9
[ 84547-61-5 ]
[ 164162-15-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

10
[ 84547-61-5 ]
2-[5-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-1-methyl-1<i>H</i>-pyrazol-4-ylmethyl]-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid allyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

11
[ 84547-61-5 ]
[ 164162-12-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

12
[ 84547-61-5 ]
C₂₇H₄₈N₃O₅S₂Si₂^(1-)*Na⁽¹⁺⁾ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982

13
[ 84547-61-5 ]
[ 164162-09-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

14
[ 84547-61-5 ]
(2R,4S)-2-(5-Hydroxymethyl-1-methyl-1H-pyrazol-4-ylmethyl)-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

15
[ 84547-61-5 ]
[5-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methyl-1H-pyrazol-4-yl]-[(2S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-methanol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

16
[ 84547-61-5 ]
[ 164162-17-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

17
[ 84547-61-5 ]
[ 164162-13-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

18
[ 84547-61-5 ]
[ 351529-78-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

19
[ 84547-61-5 ]
[ 191734-33-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

20
[ 84547-61-5 ]
[ 164162-78-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 961 - 982
[2]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

21
[ 84547-61-5 ]
[ 497852-78-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 363 - 386

22
[ 84547-61-5 ]
7-[4-(2-butoxyethoxy)phenyl]-1-isobutyl-N-[4-[[(1-methylpyrazol-5-yl)methyl]sulfinyl]phenyl]-2,3-dihydro-1-benzazepine-4-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 363 - 386

23
[ 84547-61-5 ]
4-{(2R,4S)-4-[(4R,5S,6S)-2-Carboxy-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-5-hydroxymethyl-1,2-dimethyl-2H-pyrazol-1-ium; chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

24
[ 84547-61-5 ]
4-{(2R,4S)-1-Allyloxycarbonyl-4-[(4R,5S,6S)-2-allyloxycarbonyl-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-pyrrolidin-2-ylmethyl}-5-hydroxymethyl-1,2-dimethyl-2H-pyrazol-1-ium; chloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1997,vol. 7,p. 1409 - 1414

25
[ 16034-46-1 ]
[ 84547-61-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere;	To a solution of 1 -methyl- lH-pyrazole-5-carboxylic acid (2 g, 15.86 mmol) in tetrahydrofuran (50 mL) was added L1AIH4 (720 mg, 18.97 mmol) in portions at 0 C under an inert atmosphere of nitrogen. The reaction was stirred for 2 hours at room temperature then quenched by the addition of water (2 mL). The mixture was dried over by anhydrous sodium sulfate and the solids were filtered out. The filtrates were concentrated under reduced pressure to afford (1 -methyl- lH-pyrazol- 5-yl)methanol as colorless oil (1.2 g, 67 ). (ES, m/z) [M+H]+ 113.0 *H NMR (300 MHz, CDC13) delta 7.36 (d, 7 = 1.8 Hz, 1H), 6.18 (d, 7 = 1.8 Hz, 1H), 4.66 (s, 2H), 3.88 (s, 3H)
	With dimethylsulfide borane complex; In tetrahydrofuran;Reflux;	A mixture of 1-methyl-1 H-pyrazole-5-carboxylic acid (1.0 g, 7.93 mmol), BH3. DMS (39.6 mL, 79 mmol) in THF (40 mL) was stirred at reflux overnight. The mixture was diluted with MeOH (30 mL) and stirred for 30 min, and the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with CH2Cl2/MeOH. The residue was dissolved in DCM (20 mL) and to the solution was added SOCl2(5 mL, 68.5 mmol) at room temperature. The mixture was stirred for 3 h then concentrated to afford the product as an oil which was used in the next step without further purification. MS (ESI) calc? d for (C5H7ClN2) [M+H]+, 131.0, found, 131.0

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175
[2]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605
[3]Patent: WO2014/151142,2014,A1
[4]Patent: WO2016/29454,2016,A1 .Location in patent: Page/Page column 64

26
[ 84547-61-5 ]
[ 132668-86-1 ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

27
[ 84547-61-5 ]
4-[(E)-2-(2-Methyl-2H-pyrazol-3-yl)-vinyl]-phenylamine [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

28
[ 84547-61-5 ]
[ 84547-71-7 ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

29
[ 84547-61-5 ]
<(1-methylpyrazol-5-yl)methyl>-triphenylphosphonium chloride [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1982,vol. 52,p. 2297 - 2303
Zhurnal Obshchei Khimii,1982,vol. 52,p. 2598 - 2605

30
[ 84547-61-5 ]
[ 84547-63-7 ]

Yield	Reaction Conditions	Operation in experiment
57%	With thionyl chloride; In dichloromethane; at 20℃; for 2h;	A solution of (1 -methyl- lH-pyrazol-5-yl)methanol (1.2 g, 10.71 mmol) in dichloromethane (25 mL) was treated with thionyl chloride (1.9 mL) at room temperature for 2 hours. Then the reaction was quenched by the addition of water (20 mL) and neutralized with saturated aqueous sodium carbonate. The organic layer was separated and the aqueous layer extracted with dichloromethane (3 x 20 mL). The combined organic layer was dried over by anhydrous sodium sulfate. The solids were filtered out and the filtrates were concentrated under reduced pressure to afford 5-(chloromethyl)-l -methyl-lH-pyrazole as light yellow oil (800 mg, 57 %). (ES, m/z): [M+H]+ 131.0 *H NMR (300 MHz, CDC13) delta 7.41 (d, 7 = 1.8 Hz, 1H), 6.27 (d, 7 = 1.8 Hz, 1H), 4.61 (s, 2H), 3.93 (s, 3H)
	With thionyl chloride; In dichloromethane; at 20℃; for 3h;	A mixture of 1-methyl-1 H-pyrazole-5-carboxylic acid (1.0 g, 7.93 mmol), BH3. DMS (39.6 mL, 79 mmol) in THF (40 mL) was stirred at reflux overnight. The mixture was diluted with MeOH (30 mL) and stirred for 30 min, and the mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with CH2Cl2/MeOH. The residue was dissolved in DCM (20 mL) and to the solution was added SOCl2(5 mL, 68.5 mmol) at room temperature. The mixture was stirred for 3 h then concentrated to afford the product as an oil which was used in the next step without further purification. MS (ESI) calc? d for (C5H7ClN2) [M+H]+, 131.0, found, 131.0
	With thionyl chloride; In dichloromethane; at 20℃; for 3h;	(iii) A solution of (1-methyl-1 H-pyrazol-5-yl)methanol (4.4 g, 40 mmol) in dichloromethane (30 ml) was treated with thionyl chloride (2.14 g, 1.3 ml, 18 mmol) and the reaction was stirred at room temperature for 3 hours. The solvent was evaporated and the residue co-evaporated with dichloromethane. The residue was partitioned between dichloromethane and water. The organic phase was separated and washed with saturated sodium bicarbonate solution, water, brine, then dried and evaporated to afford 5-(chloromethyl)-1-methyl-1 H-pyrazole which was used in the next step.

Reference： [1]Patent: WO2014/66795,2014,A1 .Location in patent: Paragraph 0175
[2]Patent: WO2016/29454,2016,A1 .Location in patent: Page/Page column 64
[3]Patent: WO2008/125600,2008,A2 .Location in patent: Page/Page column 30

31
[ 84547-61-5 ]
[ 1256561-69-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	With phosphorus tribromide; In dichloromethane; at 0 - 20℃; for 12h;Inert atmosphere;	To a solution of (l-methyl-lH-pyrazol-5-yl)methanol (500 mg, 4.46 mmol) in anhydrous dichloromethane (20 mL) was added PBr3 (1.21g, 4.46 mmol) at 0 C. The mixture was purged with nitrogen and stirred at room temperature for 12 h. The reaction mixture was adjusted to pH -8.5 with saturated aqueous sodium bicarbonate, and then was extracted with dichloromethane (10 mL x 3). The combined organic phase was dried by anhydrous sodium sulphate, filtered and concentrated. The residue was purified by preparative TLC (petroleum ether/ acetic ester =5: 1) to afford the title compound an off-white oil (500 mg, 64%) m/z 174.
	With phosphorus tribromide;	(1 -methyl- lH-pyrazol-5- yl)methanol, which gave 5-(bromomethyl)-l-methyl-lH-pyrazole upon reaction with phosphorous tribromide.

Reference： [1]Patent: WO2014/151142,2014,A1 .Location in patent: Paragraph 0095
[2]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 120
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 1099 - 1104

32
[ 84547-61-5 ]
[ 84476-99-3 ]
[ 1356998-45-2 ]

Yield	Reaction Conditions	Operation in experiment
1.08 g		Production Example 33 5-Fluoro-2-[(1-methyl-1H-pyrazol-5-yl)methoxy]pyridine 60% Sodium hydride (390 mg) was added to a dimethylformamide (9.0 mL) solution of <strong>[84547-61-5](1-methyl-1H-pyrazol-5-yl)methanol</strong> (1.00 g) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, 2,5-difluoropyridine (1.17 g) was added to the reaction solution, and the mixed solution was then stirred for 16 hours. Subsequently, water was added to the reaction solution, and the obtained mixture was then extracted with hexane/ethyl acetate (1/2). The organic layer was concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=95:5 to 60:40), so as to obtain the title compound (1.08 g) in the form of a colorless solid. 1H NMR (600 MHz, CHLOROFORM-d) delta ppm 3.92 (s, 3H) 5.33 (s, 2H) 6.33 (d, J=1.83 Hz, 1H) 6.73 (dd, J=9.17, 3.67 Hz, 1H) 7.35 (ddd, J=8.94, 7.57, 3.21 Hz, 1H) 7.43 (d, J=1.83 Hz, 1H) 7.99 (d, J=3.21 Hz, 1H)

Reference： [1]Patent: US2013/123500,2013,A1 .Location in patent: Paragraph 0379; 0380

33
[ 52334-81-3 ]
[ 84547-61-5 ]
[ 1356998-44-1 ]