[ CAS No. 54923-31-8 ] {[proInfo.proName]}

Name: 54923-31-8|5-Bromo-6-methylpyridin-2-ol|96%
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Quality Control of [ 54923-31-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 54923-31-8 ]

CAS No. :	54923-31-8	MDL No. :	MFCD03427653
Formula :	C₆H₆BrNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UJHCRBDEJPQFIA-UHFFFAOYSA-N
M.W :	188.02	Pubchem ID :	2734417
Synonyms :

Calculated chemistry of [ 54923-31-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.17
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.93
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) :	-6.08 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	1.92
Log Po/w (WLOGP) :	1.86
Log Po/w (MLOGP) :	1.33
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.78

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.71
Solubility :	0.368 mg/ml ; 0.00196 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.08 mg/ml ; 0.00577 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.69
Solubility :	0.383 mg/ml ; 0.00204 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 54923-31-8 ]

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

Application In Synthesis of [ 54923-31-8 ]

* 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 [ 54923-31-8 ]
Downstream synthetic route of [ 54923-31-8 ]

[ 54923-31-8 ] Synthesis Path-Upstream 1~7

1
[ 375368-83-5 ]
[ 54923-31-8 ]

Reference： [1] Patent: WO2015/89809, 2015, A1, . Location in patent: Page/Page column 74
[2] Patent: WO2015/95256, 2015, A1, . Location in patent: Page/Page column 74; 75

2
[ 42753-71-9 ]
[ 54923-31-8 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1186,1191

3
[ 1824-81-3 ]
[ 54923-31-8 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1186,1191

4
[ 3279-76-3 ]
[ 54923-31-8 ]
[ 500587-45-1 ]
[ 374633-33-7 ]

Reference： [1] Synlett, 2003, # 11, p. 1678 - 1682

5
[ 54923-31-8 ]
[ 74-88-4 ]
[ 126717-59-7 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: With silver carbonate In chloroform at 20℃; Stage #2: With triethylamine In chloroform for 1.5 h;	Example 3 3-(2,5-Dimethyl-6-oxo-1 6-dihydropyridin-3-(at)l)benzonitrile Step 1: 3-Bromo-6-methoxy-2-methylpyridine: A mixture of 5-bromo-6-methyl-1H-pyridin- 2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20percent ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2- methylpyridine (3.7 g, 63percent yield) as an oil. LC/MS RT 3.76 min; MS m/e = 202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (lH, d), 3.89 (3H, s), 2.57 (3H, s).

Reference： [1] Heterocycles, 1990, vol. 31, # 5, p. 819 - 824
[2] Patent: WO2005/97750, 2005, A1, . Location in patent: Page/Page column 71

6
[ 54923-31-8 ]
[ 100-39-0 ]
[ 126717-60-0 ]

Reference： [1] Heterocycles, 1990, vol. 31, # 5, p. 819 - 824

7
[ 54923-31-8 ]
[ 39919-65-8 ]

Reference： [1] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 95

[ 54923-31-8 ] Synthesis Path-Downstream 1~79

1
[ 42753-71-9 ]
[ 54923-31-8 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 1186,1191

2
[ 54923-31-8 ]
[ 100-39-0 ]
[ 126717-60-0 ]

Reference： [1]Heterocycles,1990,vol. 31,p. 819 - 824

3
[ 54923-31-8 ]
[ 74-88-4 ]
[ 126717-59-7 ]

Yield	Reaction Conditions	Operation in experiment
63%		Example 3 3-(2,5-Dimethyl-6-oxo-1 6-dihydropyridin-3-(at)l)benzonitrile Step 1: 3-Bromo-6-methoxy-2-methylpyridine: A mixture of 5-bromo-6-methyl-1H-pyridin- 2-one (5.5 g, 29 mmol), silver carbonate (10.89 g, 39 mmol), iodomethane (13.6 mL, 217 mmol) and chloroform (115 mL) is stirred overnight in the dark at room temperature. Triethylamine (10 mL) is added and stirring continued for 1.5 hr. The reaction mixture is filtered through a pad of Hi-Flo and the filtrate is washed with water (100 mL), dried, filtered and concentrated. The residue is purified by filtration through a pad of silica gel washing with cyclohexane-20% ethyl acetate. The solvent is concentrated to afford 3-bromo-6-methoxy-2- methylpyridine (3.7 g, 63% yield) as an oil. LC/MS RT 3.76 min; MS m/e = 202/204 (M); NMR (CDCl3) 7.6 (1H, d), 6.43 (lH, d), 3.89 (3H, s), 2.57 (3H, s).

Reference： [1]Heterocycles,1990,vol. 31,p. 819 - 824
[2]Patent: WO2005/97750,2005,A1 .Location in patent: Page/Page column 71

4
[ 3279-76-3 ]
[ 54923-31-8 ]
[ 500587-45-1 ]
[ 374633-33-7 ]

Reference： [1]Synlett,2003,p. 1678 - 1682

5
[ 1824-81-3 ]
[ 54923-31-8 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 1186,1191

6
[ 54923-31-8 ]
[ 39919-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; phosphorus(V) oxybromide; In toluene; for 4h;Reflux;	Phosphorus oxybromide (2.3 g, 8.0 mmol) was dissolved in toluene (4 mL) and <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong> (1.0 g, 5.3 mmol) was added, followed by pyridine (0.43 mL, 5.3 mmol). The reaction was heated at reflux for 4 h, then cooled to room temperature and taken up in ethyl acetate and dilute aqueous sodium bicarbonate. After separating the layers, the aqueous was extracted with ethyl acetate (2.x.). The organics were dried over sodium sulfate, concentrated in vacuo, and purified via chromatography (20 to 50percent ethyl acetate/hexanes). This provided the product, 3,6-dibromo-2-methylpyridine, as a white solid. 1H NMR (400 MHz, CDCl3) delta 2.63 (s, 3H), 7.18 (d, J=8.3 Hz, 1H), 7.62 (d, J=8.3 Hz, 1H).

Reference： [1]Patent: US2010/222345,2010,A1 .Location in patent: Page/Page column 95

7
[ 54923-31-8 ]
[ 6226-25-1 ]
[ 1375471-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In 1,4-dioxane; at 50.0℃; for 4.0h;	Intermediate 14 (3S,5S,6R)-3-Amino-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one hydrochloride; Step A: 5-Bromo-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one; To a stirred mixture of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong> (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2-trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50 C. for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 60:40, to give the title compound. MS: m/z=269.9 (M+1).
	With caesium carbonate; In 1,4-dioxane; at 50.0℃; for 4.0h;	To a stirred mixture of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong> (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2- trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50 C for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of Omicron¾Omicron2:Epsilon0Alpha? - 100:0 to 60:40, to give the title compound. MS: mlz - 269.9 (M + 1).
	With caesium carbonate; In 1,4-dioxane; at 50.0℃; for 4.0h;	Step A: 5-Bromo-6-methyl-l-(2,2,2-trifluoroethyl)pyridin-2(lH)-oneTo a stirred mixture of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong> (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2- trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50 C for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc - 100:0 to 60:40, to give the title compound. MS: mlz = 269.9 (M + 1).

With caesium carbonate; In 1,4-dioxane; at 50.0℃; for 4.0h;

Step A: 5-Bromo-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-2(1H)-one (0263) To a stirred mixture of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong> (25.0 g, 133 mmol) and cesium carbonate (52.0 g, 160 mmol) in 1,4-dioxane (600 mL) was added 2,2,2-trifluoroethyl triflate (40.1 g, 173 mmol) and the resulting mixture was heated at 50 C. for 4 h and then allowed to cool to ambient temperature. The resulting mixture was filtered and the filtrate was concentrated to dryness in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc-100:0 to 60:40, to give the title compound. MS: m/z=269.9 (M+1).

Reference： [1]Patent: US2012/122899,2012,A1 .Location in patent: Page/Page column 27
[2]Patent: WO2012/129014,2012,A1 .Location in patent: Page/Page column 38
[3]Patent: WO2013/169574,2013,A2 .Location in patent: Page/Page column 75; 76
[4]Patent: US9499541,2016,B2 .Location in patent: Page/Page column 49; 50

8
[ 54923-31-8 ]
[ 1375471-09-2 ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2012/129014,2012,A1
[3]Patent: US9499541,2016,B2

9
[ 54923-31-8 ]
[ 1375471-03-6 ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2013/169574,2013,A2
[3]Patent: US9499541,2016,B2

10
[ 54923-31-8 ]
(5SR,6RS)-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2012/129014,2012,A1

11
[ 54923-31-8 ]
(5SR,6RS)-3-azido-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2012/129014,2012,A1

12
[ 54923-31-8 ]
tert-butyl [(5SR,6RS)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-3-yl]carbamate [ No CAS ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2012/129014,2012,A1

13
[ 54923-31-8 ]
[ 1375471-07-0 ]
[ 1375471-08-1 ]

Reference： [1]Patent: US2012/122899,2012,A1
[2]Patent: WO2012/129014,2012,A1

14
[ 54923-31-8 ]
[ 1401008-12-5 ]

Reference： [1]Patent: WO2012/129014,2012,A1

15
[ 54923-31-8 ]
[ 1312789-74-4 ]

Reference： [1]Patent: US2013/203739,2013,A1

16
[ 54923-31-8 ]
[ 1312788-27-4 ]

Reference： [1]Patent: US2013/203739,2013,A1

17
[ 54923-31-8 ]
[ 17689-66-6 ]
[ 955932-47-5 ]

Yield	Reaction Conditions	Operation in experiment
1.3 g	With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 60.0℃;Cooling with ice;	Step 1> Synthesis of 4-(5-bromo-6-methylpyridin-2-yloxy)-2-methylbutan-2-ol To a suspension of sodium hydride (containing about 40% of a mineral oil, 0.38 g) in N,N-dimethylformamide (10 mL), <strong>[54923-31-8]5-bromo-2-hydroxy-6-methylpyridine</strong> (1.00 g) and 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (1.51 g) were added under ice-cooling and the resultant reaction mixture was stirred at 60 C. for 2.5 hours. To the mixture, 3-hydroxy-3-methylbutyl 4-methylbenzenesulfonate (0.50 g) was further added and the resultant reaction mixture was stirred at 60 C. for 1.5 hours. Sodium hydride (containing about 40% of a mineral oil, 40 mg) was further added. To the reaction mixture, a saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate. The organic phase was washed with brine and then dried over anhydrous sodium sulfate. From the organic phase, the solvent was removed by evaporation under reduced pressure and the resultant residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=50:50 to 33:67) to give the title compound (1.3 g) as a pale yellow oil.

Reference： [1]Patent: US2013/203739,2013,A1 .Location in patent: Paragraph 1275

18
[ 54923-31-8 ]
(5S,6R)-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]
(5R,6S)-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]

Reference： [1]Patent: WO2013/169574,2013,A2
[2]Patent: US9499541,2016,B2

19
[ 54923-31-8 ]
[ 1356924-73-6 ]
3-(((5-bromo-6-methylpyridin-2-yl)oxy)methyl)cyclobutanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 16.0h;	Step B: 3-(((5-bromo-6-methylpyridin-2-yl)oxy)methyl)cyclobutanol A mixture of (3- hydroxycyclobutyl)methyl 4-methylbenzenesulfonate (10.0 g, 39.0 mmol), 5-bromo-6- methylpyridin-2-ol (8.80 g, 46.8 mmol) and K2C03 (13.48 g, 98 mmol) in DMF (100 mL) wasstirred at 100C for 16 h. Then the reaction mixture was cooled to room temperature and poured into water (300 mL). The resulting mixture was extracted with EtOAc (100 mLx3), and the combined organic layers were washed with brine (100 mL), dried over anhydrous Mg504, and filtered. The filtrate was concentrated in vacuo to give the crude product, which was purified by flash column chromatography on silica gel (PE: EtOAc= 10: 1 to 4: 1) to give the titlecompound. ?H NMR (400 MHz, CDC13) oe: 7.59 (d, J= 8.61 Hz, 1 H), 6.43 (d, J= 8.61 Hz, 1 H),4.21 (dd, J= 9.39, 6.65 Hz, 2 H), 2.42 - 2.56 (m, 4 H), 2.06 - 2.36 (m, 3 H), 1.70 - 1.91 (m, 2 H). MS (ESI) mle (M+Hj: 272. 1/274.1

Reference： [1]Patent: WO2015/73342,2015,A1 .Location in patent: Page/Page column 107

20
[ 54923-31-8 ]
(1S,1aS,6aR)-4-((2-fluoro-5-(2-methyl-6-((tetrahydro-2H-pyran-4-yl)methoxy)pyridin-3-yl)benzyl)oxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene-1-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/89809,2015,A1

21
[ 54923-31-8 ]
1-[3-(5-bromo-6-methylpyridin-2-yloxy)propyl]cyclopropanol [ No CAS ]

Reference： [1]Patent: WO2015/89809,2015,A1

22
[ 54923-31-8 ]
(1S,1aS,6aR)-4-(2-fluoro-5-{6-[3-(1-hydroxycyclopropyl)propoxy]-2-methylpyridin-3-yl}benzyloxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene-1-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Patent: WO2015/89809,2015,A1

23
[ 54923-31-8 ]
(1S,1aS,6aR)-4-((2-fluoro-5-(6-(3-(1-hydroxycyclopropyl)propoxy)-2-methylpyridin-3-yl)benzyl)oxy)-1,1a,6,6a-tetrahydrocyclopropa[a]indene-1-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2015/89809,2015,A1

24
[ 125552-89-8 ]
[ 54923-31-8 ]
3-bromo-2-methyl-6-((tetrahydro-2H-pyran-4-yl)methoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With silver carbonate; In toluene;Reflux;	Step B.3-bromo-2-methyl-6-((tetrahydro-2H-pyran-4-yl)methoxy)pyridine To a stirred solution of <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> in toluene was added 4- bromomethyl-tetrahydro-[2H]-pyran (1 equivalent) and Ag2C( (2 equivalents). Then the mixture was heated to reflux overnight. TLC showed <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> was consumed. The mixture was filtered and the filtrate was concentrated to afford crude product which was purified by preparative TLC (PE/EA=1/1) to give the title compound. MS m/z: 287 (M+H+).
	With silver carbonate; In toluene;Reflux;	Step B.3-bromo-2-methyl-6-((tetrahydro-2H-pyran-4-yl)methoxy)pyridine To a stirred solution of <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> in toluene was added 4- bromomethyl-tetrahydro-[2H]-pyran (1 equivalent) and Ag2C( (2 equivalents). Then the mixture was heated to reflux overnight. TLC showed <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> was consumed. The mixture was filtered and the filtrate was concentrated to afford crude product which was purified by preparative TLC (PE/EA=1/1) to give the title compound. MS m/z: 287 (M+H+).

Reference： [1]Patent: WO2015/89809,2015,A1 .Location in patent: Page/Page column 74
[2]Patent: WO2015/95256,2015,A1 .Location in patent: Page/Page column 75

25
[ 54923-31-8 ]
[ 2969-81-5 ]
4-(5-bromo-6-methylpyridin-2-yloxy)butyric acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 110.0℃; for 16.0h;Inert atmosphere;	Step B.4-(5-Bromo-6-methyl-pyridin-2-yloxy)-butyric acid, ethyl ester A mixture of <strong>[54923-31-8]5-bromo-6-methyl-pyridin-2-ol</strong> (1.3 g, 6.9 mmol), 4-bromo-butyric acid ethyl ester (2.7 g, 13.8 mmol) and K2C03 (2.8 g, 20.7 mmol) in DMF (20 mL) was heated at 110C under a dry N2 atmosphere for 16 h. After cooling, the mixture was diluted with 200 mL of H2O, and twice extracted with ethyl acetate. The combined organic phase was washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (EA/PE=1/10) to give the title compound.

Reference： [1]Patent: WO2015/89809,2015,A1 .Location in patent: Page/Page column 80

26
[ 375368-83-5 ]
[ 54923-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; for 2h;Reflux;	Step A. 5-bromo-6-methylpyridin-2-ol 3-Bromo-6-fluoro-2-methylpyridine (5 g, 0.021 mol) was added into HQ (6mol/L, 40mL), and the mixture was stirred, and refluxed for 2 hours. The product was detected by TLC. After the reaction was finished, the mixture was quenched with saturated aqueous NaHC(, filtered, and concentrated to afford the title compound.
	With hydrogenchloride; water; for 2h;Reflux;	Step A. 5-bromo-6-methylpyridin-2-ol 3-Bromo-6-fluoro-2-methylpyridine (5 g, 0.021 mol) was added into HQ (6mol/L, 40mL), and the mixture was stirred, and refluxed for 2 hours. The product was detected by TLC. After the reaction was finished, the mixture was quenched with saturated aqueous NaHC(, filtered, and concentrated to afford the title compound.

Reference： [1]Patent: WO2015/89809,2015,A1 .Location in patent: Page/Page column 74
[2]Patent: WO2015/95256,2015,A1 .Location in patent: Page/Page column 74; 75

27
[ 54923-31-8 ]
1-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea [ No CAS ]
1-(2-fluoro-4-(2-methyl-6-oxo-1,6-dihydropyridin-3-yl)phenyl)-3-(4-((3-methyloxetan-3-yl)oxy)-3-(trifluoromethyl)phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26.1%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 110.0℃; for 0.25h;Microwave irradiation;	A solution of <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> (17.69 mg 0.094 mmol) 1- (2-fluoro-4- (4 4 5 5-tetramethyl-1 3 2-dioxaborolan-2-yl) phenyl) -3- (4- ( (3-methyloxetan-3-yl) oxy) -3- (trifluoromethyl) phenyl) urea (40 mg 0.078 mmol) PdCl2(dppf) (5.74 mg 7.84 mumol) and Cs2CO3(51.1 mg 0.157 mmol) in 1 4-dioxane (1.5 mL) and water (0.5 mL) was stirred at 110 on microwave for 15min. After LCMS analysis showed the starting material was disappeared. The mixture was dissolved in EA (20 mL) and washed with H2O (10 mL) . The combined organic extract was washed with brine (10 mL) dried over Na2SO4 filtered and concentrated. The residue was purified by preparative HPLC. After lyophilization a white solid of 1- (2-fluoro-4- (2-methyl-6-oxo-1 6-dihydropyridin-3-yl) phenyl) -3- (4- ( (3-methyloxetan-3-yl) oxy) -3- (trifluoromethyl) phenyl) urea (10.21 mg 0.020 mmol 26.1yield) was obtained1HNMR(400 MHz CD3OD) delta 8.13 (t J 8.6 Hz 1H) 7.78 (d J 2.4 Hz 1H) 7.55-7.50 (m 2H) 7.14-7.06 (m 2H) 6.62 (d J 8.8 Hz 1H) 6.42 (d J 9.2 Hz 1H) 4.89-4.88 (m 2H) 4.62 (d J 7.2 Hz 2H) 2.28 (s 3H) 1.72 (s 3H) ES-LCMS m/z 492.1 (M+H)

Reference： [1]Patent: WO2016/37578,2016,A1 .Location in patent: Page/Page column 191; 192

28
[ 54923-31-8 ]
1-(2-(bromomethyl)-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.7 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	Reference Production Example 33 (0647) A mixture of 3.04 g of 3A mentioned in Reference Production Example 3, 1.88 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 2.76 g of potassium carbonate, and 22 ml of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 3.70 g of 1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-chlorophenyl]-4-methyl-1,4-dihydrotetrazol-5-on e (hereinafter referred to as 33A). (0648) 1H-NMR (CDCl3) delta:7.60-7.56 (2H, m), 7.43 (1H, t, J=8.0 Hz), 7.37-7.33 (1H, m), 6.35 (1H, d, J=8.5 Hz), 5.53 (2H, s), 3.65 (3H, s), 2.49 (3H, s).
3.7 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 3.04g embodiment of preparing in the reference 3 referred to in 3A, the 1.88g <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 2.76g the potassium carbonate and 22 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 3.70g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one (called below 33A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0647; 0648
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 1027; 1028; 1029; 1030

29
[ 54923-31-8 ]
1-(2-(bromomethyl)-3-methoxyphenyl)-4-methyl-1,4-dihydro-5H-tetrazole-5-one [ No CAS ]
1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.8 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	Reference Production Example 46 (0672) A mixture of 0.60 g of 7A mentioned in Reference Production Example 7, 0.38 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 0.55 g of potassium carbonate, and 8 ml of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 0.80 g of 1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as 46A). (0673) 1H-NMR (CDCl3) delta:7.55 (1H, d, J=8.5 Hz), 7.46 (1H, t, J=8.2 Hz), 7.08 (1H, dd, J=8.5, 0.7 Hz), 7.05-7.01 (1H, m), 6.34 (1H, dd, J=8.6, 0.6 Hz), 5.43 (2H, s), 3.92 (3H, s), 3.62 (3H, s), 2.50 (3H, s).
0.80 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 0.60g in the reference embodiment of preparing 7 mentioned in 7A, the 0.38g <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 0.55g the potassium carbonate and 8 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 0.80g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazole-5-one(called below 46A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0672; 0673
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 1077; 1078; 1079; 1080

30
[ 54923-31-8 ]
1-{2-(bromomethyl)-3-methylphenyl}-4-methyl-1,4-dihydro-5H-tetrazol-5-one [ No CAS ]
1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.51 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	Reference Production Example 25 (0631) A mixture of 5.56 g of 14A mentioned in Reference Production Example 14, 3.76 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 5.53 g of potassium carbonate, and 80 ml of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 4.51 g of 1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as 25A). (0632) 1H-NMR (CDCl3) delta:7.57 (1H, d, J=8.5 Hz), 7.39-7.35 (2H, m), 7.25-7.21 (1H, m), 6.37 (1H, dd, J=8.6, 0.6 Hz), 5.35 (2H, s), 3.67 (3H, s), 2.54 (3H, s), 2.49 (3H, s).
4.51 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 5.56g in the reference embodiment of preparing 14 of the mentioned in 14A, the 3.76g <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 5.53g the potassium carbonate and 80 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 4.51g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one (called below 25A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0631; 0632
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 0995; 0996; 0997; 0998

31
[ 54923-31-8 ]
1-(2-(bromomethyl)-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-cyclopropylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.04 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	Reference Production Example 27 (0635) A mixture of 1.64 g of 16A mentioned in Reference Production Example 16, 1.00 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 1.47 g of potassium carbonate, and 21 ml of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2.04 g of 1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-cyclopropylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as 27A). (0636) 1H-NMR (CDCl3) delta:7.60 (1H, d, J=8.6 Hz), 7.42 (1H, t, J=7.9 Hz), 7.28-7.24 (2H, m), 6.40 (1H, dd, J=8.6, 0.6 Hz), 5.58 (2H, s), 3.68 (3H, s), 2.53 (3H, s), 2.27-2.22 (1H, m), 1.06-1.00 (2H, m), 0.82-0.76 (2H, m).
2.04 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 1.64g in the reference embodiment of preparing 16 mentioned in 16A, the 1.00g <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 1.47g the potassium carbonate and 21 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 2.04g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-cyclophenyl]-4-methyl-1,4-dihydrotetrazole-5-one called below 27A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0636; 0635
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 1003; 1004; 1005; 1006

32
[ 54923-31-8 ]
1-(2-(bromomethyl)-3-ethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]
1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-ethylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.04 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	Reference Production Example 26 (0633) A mixture of 1.59 g of 19A mentioned in Reference Production Example 19, 1.05 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 1.55 g of potassium carbonate, and 22 ml of acetonitrile was stirred with heating at 80 C. for 4 hours. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2.04 g of 1-[2-(5-bromo-6-methyl-pyridin-2-yloxymethyl)-3-ethylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as 26A). (0634) 1H-NMR (CDCl3) delta:7.57 (1H, d, J=8.5 Hz), 7.45-7.39 (2H, m), 7.26-7.21 (1H, m), 6.36 (1H, d, J=8.7 Hz), 5.36 (2H, s), 3.65 (3H, s), 2.89 (2H, q, J=7.6 Hz), 2.49 (3H, s), 1.28 (3H, t, J=7.6 Hz).
2.04 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 1.59g embodiment of the reference preparation of 19 referred to in 19A, 1.05g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 1.55g the potassium carbonate and 22 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 2.04g of 1-[2-(5-bromo-6-methylpyridine-2-yloxymethyl)-3-ethylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one (called below 26A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0633; 0634
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 0999; 1000; 1001; 1002

33
[ 54923-31-8 ]
1-[2-(3-bromo-5-phenyl-6-methyl-pyridin-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]

Reference： [1]Patent: US2016/157489,2016,A1
[2]Patent: CN105492432,2016,A

34
[ 54923-31-8 ]
5-bromo-6-hydroxyl-2-methyl-3-phenylpyridine [ No CAS ]

Reference： [1]Patent: US2016/157489,2016,A1
[2]Patent: CN105492432,2016,A

35
[ 54923-31-8 ]
[ 98-80-6 ]
[ 84596-29-2 ]

Yield	Reaction Conditions	Operation in experiment
0.3 g	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; for 4.0h;Reflux;	Reference Production Example 34 (0649) A mixture of 0.94 g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 0.91 g of phenylboronic acid, 3.18 g of tripotassium phosphate, 2.0 ml of water, 0.08 g of [1,1?-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 20 ml of dimethoxyethane was stirred with heating under reflux for 4 hours. After cooling, the reaction solution was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography to obtain 0.30 g of 6-hydroxy-2-methyl-3-phenylpyridine (hereinafter referred to as 34A). (0650) 1H-NMR (CDCl3) delta:7.46-7.39 (3H, m), 7.37-7.32 (1H, m), 7.28-7.26 (2H, m), 6.51 (1H, d, J=9.2 Hz), 2.38 (3H, s).
0.30 g	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; for 4.0h;Reflux;	The 0.94g of <strong>[54923-31-8]3-bromo-6-hydroxy-2-methylpyridine</strong>, 0.91g the phenyl boronic acid, 3.18g of potassium phosphate, 2.0 ml of water, 0.08g the [1,1 the [...] -bis (diphenylphosphino) ferrocene] palladium dichloride (II) dichloromethane adduct and 20 ml of dimethoxyethane mixture of heating to reflux with stirring in 4 hours. After cooling, the reaction solution is concentrated under reduced pressure. The residue thus obtained by silica gel column chromatography, to obtain 0.30g of the 6-hydroxyl-2-methyl-3-phenylpyridine (called below 34A).

Reference： [1]Patent: US2016/157489,2016,A1 .Location in patent: Paragraph 0649; 0650
[2]Patent: CN105492432,2016,A .Location in patent: Paragraph 1031; 1032; 1033; 1034

36
[ 54923-31-8 ]
1-{2-(bromomethyl)-3-methylphenyl}-4-methyl-1,4-dihydro-5H-tetrazol-5-one [ No CAS ]
1-[2-(3-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.08 g	With potassium carbonate; In acetonitrile; at 80.0℃; for 4.0h;	The 2.83g in the reference embodiment of preparing 14 of the mentioned in 14A, the 1.88g 3-bromo-2-hydroxy-6-methylpyridine, 2.76g the potassium carbonate and 40 ml of a mixture of acetonitrile in the accompanying 80 C heating and stirring of 4 hours. The water added to the reaction mixture and the mixture is extracted with chloroform. The organic layer with saturated aqueous salt solution washing, drying by anhydrous magnesium sulfate, and concentrated under reduced pressure, to obtain 4.08g of 1-[2-(3-bromo-6-methylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazole-5-one (called below 36A).

Reference： [1]Patent: CN105492432,2016,A .Location in patent: Paragraph 1039; 1040; 1041; 1042

37
[ 54923-31-8 ]
1-[2-(3,6-dimethyl-5-phenylpyridine-2-yloxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one [ No CAS ]

Reference： [1]Patent: CN105492432,2016,A

38
[ 54923-31-8 ]
(5S,6R)-3-azido-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]
(5R,6S)-3-azido-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-2-one [ No CAS ]

Reference： [1]Patent: US9499541,2016,B2

39
[ 54923-31-8 ]
tert-butyl ((5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-3-yl)carbamate [ No CAS ]
tert-butyl [(5R,6S)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-3-yl]carbamate [ No CAS ]

Reference： [1]Patent: US9499541,2016,B2

40
[ 54923-31-8 ]
[ 1375471-08-1 ]

Reference： [1]Patent: US9499541,2016,B2

41
[ 54923-31-8 ]
[ 1375471-07-0 ]

Reference： [1]Patent: US9499541,2016,B2

42
[ 54923-31-8 ]
(5S,6R)-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-2-one [ No CAS ]
(5R,6S)-6-methyl-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-2-one [ No CAS ]

Reference： [1]Patent: US9499541,2016,B2

43
[ 54923-31-8 ]
(2R)-N-[(3S,5S,6R)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,5-trifluorophenyl)piperidin-3-yl]-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: US9499541,2016,B2

44
[ 54923-31-8 ]
5-bromo-3-chloro-1,6-dimethylpyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: WO2019/28302,2019,A1

45
[ 54923-31-8 ]
5-bromo-3-chloro-6-methylpyridin-2-ol [ No CAS ]
C₆H₄BrCl₂NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide; In tetrahydrofuran; at 60.0℃; for 3.0h;	A solution containing <strong>[54923-31-8]5-bromo-6-methylpyridin-2-ol</strong> (1 g, 5.32 mmol) and NCS (0.852 g, 6.38 mmol) in THF (20 mL) was heated at 60 C for 2 h. Additional NCS (-100 mg) was added and the reaction mixture was heated for an additional 1 h, cooled to room temperature and concentrated to dryness. The residue was re-suspended in diethyl ether/hexanes (20 mL, 9/1), stirred and sonicated for lh. The solids were collected and rinsed with additional ether/hexanes mixture (20 mL, 9/1). The filtrate was re- concentrated -1/2 volume to afford second crop of 5-bromo-3-chloro-6-methylpyridin-2- ol (1 g total), m/z (224, M+H). The product was contaminated with -10% of a bis chlorinated material, m/z (268, M+H).

Reference： [1]Patent: WO2019/28302,2019,A1 .Location in patent: Page/Page column 60

46
[ 54923-31-8 ]
tert-butyl 4-(2-(5-chloro-1,2-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)-3-isopropyl-1H-indol-5-yl)piperidine-1-carboxylate [ No CAS ]
C₄₉H₆₅N₅O₅ [ No CAS ]

Reference： [1]Patent: WO2019/28302,2019,A1

47
[ 54923-31-8 ]
[ 86604-75-3 ]
2-[(5-bromo-6-methylpyridin-2-yl)oxy]methyl}-4-methoxy-3,5-dimethylpyridine [ No CAS ]