867267-28-5|5-Hydroxy-2-methoxyisonicotinaldehyde| Ambeed

Structure of 867267-28-5

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Quality Control of [ 867267-28-5 ] Purity: 97% SDS Specification

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Product Details of [ 867267-28-5 ]

CAS No. :	867267-28-5
Formula :	C₇H₇NO₃
M.W :	153.14
SMILES Code :	O=CC1=C(O)C=NC(OC)=C1
MDL No. :	MFCD13189872
InChI Key :	GRJJLRLFOQLVKR-UHFFFAOYSA-N
Pubchem ID :	72212498

Safety of [ 867267-28-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 867267-28-5 ]

* 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.

Downstream synthetic route of [ 867267-28-5 ]

[ 867267-28-5 ] Synthesis Path-Downstream 1~54

1
[ 867267-27-4 ]
[ 867267-28-5 ]

Yield	Reaction Conditions	Operation in experiment
55%	With hydrogenchloride; In tetrahydrofuran; water; at 50℃; for 0.5h;	Step 3 ;To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (10 g, 0.05 mol) in THF (100 mL) was added 3 N HCl (150 mL). The reaction was stirred at 50 C. for 30 min, cooled to rt, and diluted with water (100 mL). The mixture was neutralized to pH 7-8 and extracted with EtOAc (200 mL) three times. The organic layer was dried over Na2SO4 and concentrated to give 5-hydroxy-2-methoxyisonicotinaldehyde (4.2 g, 55%) as a yellow solid. 1H NMR (400 MHz; DMSO) δ=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H).
	With hydrogenchloride; In tetrahydrofuran; at 50℃; for 0.5h;	[0172] To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (10 g, 0.05 mol) in THF (100 mL) was added 3 N HC1 (150 mL). The reaction was stirred at 50 C for 30 mm, cooled to rt, and diluted with water (100 mL). The mixture was neutralized to pH 7-8 and extracted with EtOAc (200 mL) three times. The organic layer was dried over Na2SO4 andconcentrated to give 5-hydroxy-2-methoxyisonicotinaldehyde (4.2 g, 55%) as a yellow solid. 1H NMR (400 MHz; DMSO) δ= l0.31(s, 1 H), 8.03 (s, 1 H), 6.89 (s, 1 H), 3.80 (s, 3 H).
	With hydrogenchloride; In tetrahydrofuran; at 50℃; for 1h;	[02601 To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol,1 eq.) in THF (150 mL) was added HC1 (3 N, 250 mL, 4.4 eq.). The reaction was stirred at 50 Cfor 1 h, cooled to rt, and diluted with water (500 mL). The mixture was neutralized to pH 7-8with solid K2C03. The pale yellow solid was collected, washed with water, and dried to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%) as a pale yellow solid. 1H NMR (400 MHz; DMSO) = 10.31 (s, 1 H), 8.03 (s, 1 H), 6.89 (s, 1 H), 3.80 (s, 3 H). LRMS (M+H+) m/z 154.0.

17.9 g	With hydrogenchloride; water; In tetrahydrofuran; at 50℃; for 1h;	To a solution of 2-methoxy-5-(methoxymethoxy)isonicotinaldehyde (33.5 g, 0.17 mol) in THF (150 mL) was added HCl (3 N, 250 mL). The reaction was stirred at 50 C. for 1 h, cooled to RT and diluted with water (500 mL). The mixture was neutralized to pH 7-8 with solid K2CO3. The pale yellow solid was collected, washed with water, and dried in vacuum oven (40 C.) overnight to give 5-hydroxy-2-methoxyisonicotinaldehyde (17.9 g, 74.6%). 1H NMR (400 MHz; DMSO)=10.31 (s, 1H), 8.03 (s, 1H), 6.89 (s, 1H), 3.80 (s, 3H); MS (ESI) m/z 154.0 [M+H]+.
600 mg	With hydrogenchloride; In tetrahydrofuran; at 70℃; for 2h;	To a stirred solution of 2-methoxy-5-methoxymethoxypyridine-4-carbaldehyde (1.5 g, 7.61 mmol) in THF (3 mL) was added 3N HC1 (15 mL) at room temperature and the reaction mixture was heated to 70C for 2 hr. The reaction mixture was cooled under ice bath, neutralizedwith K2C03 and extracted with ethyl acetate (50 mL x 2). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to provide the crude product which was purified by column chromatography to afford 600 mg of 5-hydroxy-2-methoxy-pyridine-4- carbaldehyde. ‘H-NMR (DMSO-d6, 400 MHz): ö 10.33 (s, 1H), 10.30 (s, 1H), 8.02 (s, 1H), 6.88 (s, 1H), 3.79 (s, 3H).

References: [1]Synlett,2005,p. 2080 - 2082.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1364 - 1376.
[3]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0366; 0367; 0494; 0495.
[4]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.
[5]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0172.
[6]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0260.
[7]Patent: US2014/275008,2014,A1 .Location in patent: Paragraph 0281-0282.
[8]Patent: WO2014/186035,2014,A1 .Location in patent: Page/Page column 152; 153.

2
[ 867267-28-5 ]
[ 74-88-4 ]
[ 867267-25-2 ]

Yield	Reaction Conditions	Operation in experiment
99%		2,5-Dimethoxyisonicotinaldehyde (52). A mixture of 51 (1.28 g, 8.36 mmol) and potassium carbonate(1.73 g, 12.5 mmol) in DMF (50 mL, anhydrous) was heated at 50 C for 10 min. Methyl iodide(1.42 g, 10.0 mmol) was then added and the mixture stirred at this temperature for 2 h. The resultantsolution was diluted with EtOAc and washed with brine three times. The organic layer was dried and evaporated to aord the product 52 (1.39 g, 99%) [23]. 1H NMR (CDCl3) 10.43 (s, 1H), 8.01 (s, 1H),7.08 (d, J = 0.6 Hz, 1H), 3.97 (s, 3H), 3.91 (s, 3H). LRMS: calculated for C8H9NO3: 167.1; found: [M + H]= 168.2.
82%		A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (S31) (2.50 g, 16.33 mmol) and potassium carbonate (3.39 g, 24.45 mmol) in DMF (80 mL, anhydrous) was heated at 50 C for 10 min. Methyl iodide (1.22 ml, 19.59 mmol) was then added and the mixture stirred at this temperature for 2 h. The resultant solution was diluted with EtOAc and washed with brine three times. The organic layer was dried and evaporated to afford 2,5-dimethoxyisonicotinaldehyde (S32). Yield = 2.25 g, 82%. 1H NMR (CDCl3) d 10.4 (s, 1H), 8.01 (s, 1H), 7.07 (s, 1H), 3.97 (s, 3H), 3.91 (s, 3H). Found [M+MeOH]= 200.4

References: [1]Molecules,2020,vol. 25.
[2]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1364 - 1376.
[3]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1292 - 1307.
[4]Synlett,2005,p. 2080 - 2082.

3
[ 867267-28-5 ]
(Z)-2-Azido-3-(2,5-dimethoxy-pyridin-4-yl)-acrylic acid methyl ester [ No CAS ]

References: [1]Synlett,2005,p. 2080 - 2082.

4
[ 867267-28-5 ]
[ 867267-35-4 ]

References: [1]Synlett,2005,p. 2080 - 2082.

5
[ 51834-97-0 ]
[ 867267-28-5 ]

References: [1]Synlett,2005,p. 2080 - 2082.
[2]Patent: WO2013/102145,2013,A1 .
[3]Patent: WO2013/102145,2013,A1 .
[4]Patent: WO2013/102145,2013,A1 .
[5]Patent: WO2013/102145,2013,A1 .
[6]Patent: US2014/275152,2014,A1 .
[7]Patent: US2014/275008,2014,A1 .
[8]Patent: WO2014/186035,2014,A1 .
[9]Patent: US2015/344483,2015,A1 .
[10]Patent: US2015/344483,2015,A1 .
[11]Patent: US2015/344483,2015,A1 .
[12]Patent: US2015/344483,2015,A1 .
[13]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.
[14]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 1292 - 1307.
[15]Molecules,2020,vol. 25.

6
[ 431942-25-5 ]
[ 867267-28-5 ]

References: [1]Synlett,2005,p. 2080 - 2082.
[2]Patent: WO2013/102145,2013,A1 .
[3]Patent: WO2013/102145,2013,A1 .
[4]Patent: US2014/275152,2014,A1 .
[5]Patent: US2014/275008,2014,A1 .
[6]Patent: WO2014/186035,2014,A1 .
[7]Patent: US2015/344483,2015,A1 .
[8]Patent: US2015/344483,2015,A1 .
[9]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.

7
[ 867267-28-5 ]
[ 167883-99-0 ]
5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With potassium carbonate; In N,N-dimethyl-formamide; at 125℃; for 0.25h;Microwave irradiation;	[0173] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (723.6 mg, 4.7 mmol), 8- (chloromethyl)-imidazol{1,2-a] pyridine (785 mg, 4.7 mmol), and K2C03 (1.9 g, 14.1 mmol) in DMF (20 mL) was heated at microwave reactor at 125 C for 15 mm. The mixture was filteredand concentrated. The residue was purified on silica gel (50-100% EtOAc in hexanes) to give 5- (imidazo[l,2-a]pyridin-8-ylmethoxy)-2-methoxyisonicotinaldehyde (500 mg, 38%) as an off- white solid. 1H NMR (400 MHz; DMSO) = 10.37 (s, 1 H), 8.58 (d, 1 H), 8.39 (s, 1 H), 8.02 (s, 1 H), 7.61 (s, 1 H), 7.44 (d, 1 H), 6.98 (s, 1 H), 6.93 (t, 1 H), 5.61 (s, 2 H), 3.84 (s, 3 H). LRMS (M+H+) m/z 284.0.
38%	With potassium carbonate; In N,N-dimethyl-formamide; at 125℃; for 0.25h;	Step 4 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (723.6 mg, 4.7 mmol), 8-(chloromethyl)-imidazol[1,2-a]pyridine (785 mg, 4.7 mmol), and K2CO3 (1.9 g, 14.1 mmol) in DMF (20 mL) was heated at microwave reactor at 125 C. for 15 min. The mixture was filtered and concentrated. The residue was purified on silica gel (50-100% EtOAc in hexanes) to give 5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxyisonicotinaldehyde (500 mg, 38%) as an off-white solid. 1H NMR (400 MHz; DMSO) 6=10.37 (s, 1H), 8.58 (d, 1H), 8.39 (s, 1H), 8.02 (s, 1H), 7.61 (s, 1H), 7.44 (d, 1H), 6.98 (s, 1H), 6.93 (t, 1H), 5.61 (s, 2H), 3.84 (s, 3H). LRMS (M+H+) m/z 284.0.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0173.
[2]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0361; 0368; 0369.
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.

8
[ 867267-28-5 ]
5-((2-(2H-tetrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .

9
[ 867267-28-5 ]
2-methoxy-5-[[2-(4-methyl-1H-pyrazol-5-yl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

10
[ 867267-28-5 ]
5-((3-(1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .

11
[ 867267-28-5 ]
2-(5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxypyridin-4-yl)thiazolidine [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

12
[ 867267-28-5 ]
1-(2-(5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-methoxypyridin-4-yl)thiazolidin-3-yl)ethanone [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

13
[ 867267-28-5 ]
methyl 3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinate [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

14
[ 867267-28-5 ]
5-((2-(2-hydroxypropan-2-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

15
[ 867267-28-5 ]
5-((2-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

16
[ 867267-28-5 ]
5-((2-(2-isopropyl-2H-1,2,4-triazol-3-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

17
[ 867267-28-5 ]
5-((2-(4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

18
[ 867267-28-5 ]
2-(5-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .

19
[ 867267-28-5 ]
3-(3-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoic acid [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .

20
[ 867267-28-5 ]
2-methoxy-5-((2-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.

21
[ 867267-28-5 ]
5-((2-(1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde dihydrochloride [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.

22
[ 867267-28-5 ]
3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)picolinonitrile [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

23
[ 867267-28-5 ]
2-methoxy-5-((2-(4-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

24
[ 867267-28-5 ]
2-methoxy-5-((3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)isoquinolin-4-yl)methoxy)isonicotinaldehyde [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

25
[ 867267-28-5 ]
5-(imidazo[1,2-a]pyridin-8-ylmethoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde formate [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

26
[ 867267-28-5 ]
3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinic acid [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

27
[ 867267-28-5 ]
3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinonitrile [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

28
[ 867267-28-5 ]
1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)ethanone [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

29
[ 867267-28-5 ]
2-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-2-ol [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

30
[ 867267-28-5 ]
5-((2-bromopyridin-3-yl)methoxy)-4-(1,3-dioxolan-2-yl)-2-methoxypyridine [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

31
[ 867267-28-5 ]
3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)picolinohydrazide [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

32
[ 867267-28-5 ]
4-(1,3-dioxolan-2-yl)-5-((2-(2-isopropyl-2H-1,2,4-triazol-3-yl)pyridin-3-yl)methoxy)-2-methoxypyridine [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

33
[ 867267-28-5 ]
1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)propan-1-one [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

34
[ 867267-28-5 ]
(E)-1-(3-((4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-3-(dimethylamino)-2-methylprop-2-en-1-one [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

35
[ 867267-28-5 ]
4-(1,3-dioxolan-2-yl)-5-((2-(1-isopropyl-4-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxypyridine [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .
[2]Patent: US2015/344483,2015,A1 .

36
[ 867267-28-5 ]
methyl 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinate [ No CAS ]

References: [1]Patent: WO2013/102145,2013,A1 .

37
[ 867267-28-5 ]
[ 944906-87-0 ]
5-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h;	Step 3 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (306 mg, 2 mmol, 1 eq.), 2-bromo-3-(chloromethyl)pyridine (crude above, 2 mmol), and K2CO3 (828 mg, 6 mmol, 3 eq.) in DMF (1.0 mL) was heated at 50 C. for 2 h. The mixture was cooled and added to water (50 mL) dropwise. The precipitate was filtered, washed with water, dried under high vacuo to give 5-((2-bromopyridin-3-yl)methoxy)-2-methoxyisonicotinaldehyde (350 mg, 85%) as an yellow solid. 1H NMR (400 MHz; CDCl3) δ=10.51 (s, 1H), 8.42 (dd, 1H), 8.09 (s, 1H) 7.91 (d, 1H), 7.40 (dd, 1H), 7.15 (s, 1H), 5.27 (s, 2H), 3.95 (s, 3H). LRMS (M+H+) m/z 323.0.
	With potassium carbonate; In N,N-dimethyl-formamide; at 50℃; for 2h;	[0185] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (306 mg, 2 mmol, 1 eq.), 2-bromo-3-(chloromethyl)pyridine (crude above, 2 mmol), and K2C03 (828 mg, 6 mmol, 3 eq.) inDMF (1.0 mL) was heated at 50 C for 2 h. The mixture was cooled and added to water (50 mL)dropwise. The precipitate was filtered, washed with water, dried under high vacuo to give 5-((2-bromopyridin-3 -yl)methoxy)-2-methoxyisonicotinaldehyde (350 mg, 85%) as an yellow solid. 1H NMR (400 MHz; CDC13) 6 = 10.51 (s, 1 H), 8.42 (dd, 1 H), 8.09 (s, 1 H) 7.91 (d, 1 H), 7.40 (dd, 1 H), 7.15 (s, 1 H), 5.27 (s, 2 H), 3.95 (s, 3 H). LRMS (M+H+) mz 323.0.

References: [1]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0383; 0384; 0390.
[2]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0185.
[3]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.

38
[ 867267-28-5 ]
methyl 5-(chloromethyl)nicotinate hydrochloride [ No CAS ]
methyl 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	[0199] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (352 mg, 2.29 mmol, 1 eq.), methyl 5-(chloromethyl)nicotinate hydrochloride (506 mg, 2.29 mmol, leq.), and K2C03 (1.26 g, 9.16 mmol, 4 eq.) in DMF (8.0 mL) was heated at 60 C for 3 h. The mixture was cooled and added into water (50 mL) dropwise. The precipitate was filtered, washed with water, and dried to give methyl 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinate (350 mg, 85%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.47 (s, 1H), 9.26 (d,J= 2.0 Hz, 1H), 8.90 (d, J= 2.2 Hz, lH), 8.42 (t,J= 2.1 Hz, 1H), 8.09 (s, 1H), 7.15 (s, 1H), 5.29 (s, 2H), 4.01 (s, 3H), 3.95(s, 3H). LRMS (M+H+) m/z 303.1.
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 3h;	Step 1 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (352 mg, 2.29 mmol, 1 eq.), methyl 5-(chloromethyl)nicotinate hydrochloride (506 mg, 2.29 mmol, 1 eq.), and K2CO3 (1.26 g, 9.16 mmol, 4 eq.) in DMF (8.0 mL) was heated at 60 C. for 3 h. The mixture was cooled and added into water (50 mL) dropwise. The precipitate was filtered, washed with water, and dried to give methyl 5-((4-formyl-6-methoxypyridin-3-yloxy)methyl)nicotinate (350 mg, 85%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 10.47 (s, 1H), 9.26 (d, J=2.0 Hz, 1H), 8.90 (d, J=2.2 Hz, 1H), 8.42 (t, J=2.1 Hz, 1H), 8.09 (s, 1H), 7.15 (s, 1H), 5.29 (s, 2H), 4.01 (s, 3H), 3.95 (s, 3H). LRMS (M+H+) m/z 303.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0199.
[2]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0400; 0401.

39
[ 867267-28-5 ]
[ 1446321-85-2 ]
2-methoxy-5-((1-methyl-1H-indazol-4-yl)methoxy)isonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; for 2h;Reflux;	[0215] A mixture of 2-hydroxy-5-methoxyisonicatinaldehyde (170 mg, 1.12 mmol), 4-(chloromethyl)- 1-methyl-1H-indazole (1.12 mmol), and K2C03 (618 mg, 4.48 mmol) is refluxed in CH3CN (20 mL) for 2 h. The mixture is filtered and the solid is washed with DCM. Thefiltrate is concentrated and purified on silica gel using a mixture of EtOAc and MeOH as eluent to give 5-methoxy-2-(( 1-methyl-1H-indazol-4-yl)methoxy)isonicatinaldehyde as a white solid.

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 321 - 326.
[2]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0215.

40
[ 867267-28-5 ]
3-(chloromethyl)-2-(1-methyl-1H-pyrazol-5-yl)pyridine hydrochloride [ No CAS ]
2-methoxy-5-((2-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)isonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	[0233] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (147 mg, 0.96 mmol, 1 eq.), 3- (chloromethyl)-2-( 1 -methyl- 1H-pyrazol-5-yl)pyridine hydrochloride (236 mg, 0.96 mmol, 1 eq.), and K2C03(532 mg, 3.85 mmol, 3 eq.) in DMF (3.0 mL) was heated at 70 C for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 2-methoxy-5-((2-( 1 -methyl- 1H-pyrazo 1-5-yl)pyridin-3- yl)methoxy)isonicotinaldehyde (232.5 mg, 75%) as an off-white solid. 1H NMR (400 MHz, CDCl3) 5 10.40 (s, 1H), 8.77 (dd,J= 4.7, 1.7 Hz, 1H), 8.03 (dd, J= 7.9, 1.7 Hz, 1H), 7.93 (s, 1H), 7.55 (d, J- 1.9 Hz, 1H), 7.44 (dd, J = 7.9, 4.8 Hz, 1H), 7.1 1 (d, J= 0.4 Hz, 1H), 6.43 (d, J = 1.9 Hz, 1H), 5.20 (s, 2H), 3.97 (s, 3H), 3.92 (s, 3H). LRMS (M+H+) m/z 325.1

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0233.

41
[ 867267-28-5 ]
3-chloro-4-(chloromethyl)isoquinoline [ No CAS ]
5-((3-chloroisoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14%	With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; for 1h;	[0244] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (73 mg, 0.48 mmol, 1 eq.), 3- chloro-4-(chloromethyl)isoquinoline (crude above, 0.48 mmol), and K2C03 (265 mg, 1.92 mmol, 4 eq.) in DMF (2.0 mL) was heated at 60 C for 1 h. The mixture was cooled, filtered, concentrated to dryness. The crude was purified on silica gel using a mixture of EtOAc and hexanes to give 5-((3-chloroisoquinolin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (22 mg,.14%) as an yellow solid. 1H NMR (400 MHz; CDCl3) = 10.19 (s, 1 H), 9.05 (s, 1 H), 8.23 (s, 1 H) 8.06 (d, 1 H), 7.98 (d, 1 H), 7.76 (t, 1 H), 7.63 (t, 1 H), 7.01 (s, 1H), 5.72 (s, 2 H), 3.87 (s, 3H). LRMS (M+H+) m/z 329.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0244.

42
[ 867267-28-5 ]
3-(chloromethyl)-2-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride [ No CAS ]
5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-methoxy isonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	[0263] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (395 mg, 2.58 mmol, 1 eq.), 3- (chloromethyl)-2-(l-isopropyl-lH-pyrazol-5-yl)pyridine hydrochloride (700 mg, 2.58 mmol, 1 eq.), and K2C03(1.4 g, 10.32 mmol, 4 eq.) in DMF (10.0 mL) was heated at 70 C for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((2-(l-isopropyl-lH-pyrazol-5-yl)pyridin-3-yl)methoxy)-2- methoxyisonicotinaldehyde (590 mg, 65%) as an off-white solid. 1H NMR (400 MHz, CDC13) δ 10.41 (s, 1H), 8.76 (dd, J= 4.7, 1.6 Hz, 1H), 8.04 (dd, J= 7.9, 1.6 Hz, 1H), 7.90 (s, 1H), 7.61 (d, J= 1.8 Hz, 1H), 7.44 (dd, J = 7.9, 4.8 Hz, 1H), 7.10 (s, 1H), 6.37 (d, J= 1.8 Hz, lH), 5.14 (s, 2H), 4.65 (sep, J = 6.6 Hz, 1H), 3.91 (s, 3H), 1.49 (d, J= 6.6 Hz, 6H). LRMS (M+H+) m/z 353.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0263.

43
[ 867267-28-5 ]
4-(chloromethyl)-3-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride [ No CAS ]
5-((3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methoxy)-2-methoxyisonicotinaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 2h;	[02841 A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (79 mg, 0.52 mmol, 1.5 eq.), 4- (chloromethyl)-3 -(1 -isopropyl- 1 H-pyrazol-5-yl)pyridine hydrochloride (crude above, 0.35 mmol), and K2C03 (145 mg, 1.05 mmol, 3 eq.) in DMF (10.0 mL) was heated at 100C for2 h. The mixture was cooled, filtered, concentrated, and purified on RP-HPLC (Gemini 21.2 x 150 mm) twice using a mixture of CH3CN/water (0.1% HCOOH) as eluent to give 5-((3-(1-isopropyl- I H-pyrazol-5 -yl)pyridin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (6.0 mg, 5%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.29 (s, 1H), 8.63 (s, 111), 8.42 (s, 1H), 7.67 (s, 1H), 7.54 (s, 1 H), 7.52 (d, J= 1.7 Hz, 111), 6.96 (s, 1H), 6.15 (d, J= 1.8 Hz, 1H), 4.87 (s, 2H), 4.06 (sep,J= 6.6 Hz, 1H), 3.75 (s, 311), 1.31 (d,J= 6.6 Hz, 6H). LRMS (M+H+) m/z 353.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0284.

44
[ 867267-28-5 ]
2-(chloromethyl)-3-(1-isopropyl-1H-pyrazol-5-yl)pyrazine hydrochloride [ No CAS ]
2-methoxy-5-[[3-(2-propan-2-ylpyrazol-3-yl)pyrazin-2-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.5h;	[0293] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (110 mg, 0.60 mmol, 1.2 eq.), 2- (chloromethyl)-3-(l-isopropyl-lH-pyrazol-5-yl)pyrazine hydrochloride (crude above, 0.5 mmol, 1 eq.), and K2C03(207 mg, 1.50 mmol, 3 eq.) in DMF (15.0 mL) was heated at 100 C for 30 min. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((3-(l-isopropyl-lH-pyrazol-5-yl)pyrazin-2-yl)methoxy)- 2-methoxyisonicotinaldehyde (12.0 mg, 68%) as an off-white solid. 1H NMR (400 MHz, CDCl3) 5 10.31 (s, 1H), 8.73 (d, J= 2.4 Hz, 1H), 8.65 (d, J= 2.4 Hz, 1H), 8.05 (s, 1H), 7.61 (d, J= 1.9 Hz, 1H), 7.06 (s, 1H), 6.49 (d, J= 1.9 Hz, 1H), 5.32 (s, 2H), 4.68 (sep, J= 6.6 Hz, 1H), 3.89 (s, 2H), 1.48 (d,J= 6.6 Hz, 6H). LRMS (M+H+) m/z 354.1.
68%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 0.5h;	Step 4 _A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (110 mg, 0.60 mmol, 1.2 eq.), 2-(chloromethyl)-3-(1-isopropyl-1H-pyrazol-5-yl)pyrazine hydrochloride (crude above, 0.5 mmol, 1 eq.), and K2CO3 (207 mg, 1.50 mmol, 3 eq.) in DMF (15.0 mL) was heated at 100 C. for 30 min. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give 5-((3-(1-isopropyl-1H-pyrazol-5-yl)pyrazin-2-yl)methoxy)-2-methoxyisonicotinaldehyde (12.0 mg, 68%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.31 (s, 1H), 8.73 (d, J=2.4 Hz, 1H), 8.65 (d, J=2.4 Hz, 1H), 8.05 (s, 1H), 7.61 (d, J=1.9 Hz, 1H), 7.06 (s, 1H), 6.49 (d, J=1.9 Hz, 1H), 5.32 (s, 2H), 4.68 (sep, J=6.6 Hz, 1H), 3.89 (s, 2H), 1.48 (d, J=6.6 Hz, 6H). LRMS (M+H+) m/z 354.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0293.
[2]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0542; 0543.

45
[ 867267-28-5 ]
[ 107-21-1 ]
4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With toluene-4-sulfonic acid; In toluene;Reflux;	[0319] To <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (1.0 g, 6.54 mmol, 1.0 eq.) in toluene (50.0 mL) were added ethane- 1,2-diol (10.0 mL) and PTSA (248 mg, 1.31 mmol, 0.2 eq.). The mixture was heated to reflux O/ , cooled to rt, neutralized to pH 8, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2S04, and concentrated to give 4-(l,3-dioxolan-2-yl)-6-methoxypyridin-3-ol (980 mg, 76%) as an off-white solid. LRMS (M+H+) m/z 198.1.
76%	With toluene-4-sulfonic acid; In toluene;Reflux;	Step 1 ;To <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (1.0 g, 6.54 mmol, 1.0 eq.) in toluene (50.0 mL) were added ethane-1,2-diol (10.0 mL) and PTSA (248 mg, 1.31 mmol, 0.2 eq.). The mixture was heated to reflux O/N, cooled to rt, neutralized to pH 8, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give 4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-ol (980 mg, 76%) as an off-white solid. LRMS (M+H+) m/z 198.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0319.
[2]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0590; 0591.

46
[ 867267-28-5 ]
ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate hydrochloride [ No CAS ]
ethyl 2-(5-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	[0340] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (107mg, 0.70 mmol, 1 eq.), ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-lH-pyrazol-l-yl)acetate hydrochloride (220 mg, 0.70 mmol, 1 eq.), and K2C03(386 mg, 2.8 mmol, 4 eq.) in DMF (6.0 mL) was heated at 70 C for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtO Ac and hexanes as eluent to give ethyl 2-(5-(3-((4-formyl-6-methoxypyridin-3- yloxy)methyl)pyridin-2-yl)-lH-pyrazol-l-yl)acetate (261 mg, 94%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.45 (s, 1H), 8.69 (d, J= 3.8 Hz, 1H), 8.02 (s, 1 H), 8.01 (d, J= 7.5 Hz, 1H), 7.63 (d, J = 1.6 Hz, 1H), 7.40 (dd, J= 7.6, 4.0 Hz, 1H), 7.13 (s, 1H), 6.53 (d, J= 1.6 Hz, 1H), 5.30 (s, 2 H), 5.28 (s, 2H), 4.12 (q, J= 7.1 Hz, 2H), 3.93 (s, 3H), 1.18 (t, J- 7.1 Hz, 3H). LRMS (M+H+) m/z 397.1.
94%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	Step 3 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (107 mg, 0.70 mmol, 1 eq.), ethyl 2-(5-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate hydrochloride (220 mg, 0.70 mmol, 1 eq.), and K2CO3 (386 mg, 2.8 mmol, 4 eq.) in DMF (6.0 mL) was heated at 70 C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give ethyl 2-(5-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)acetate (261 mg, 94%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.45 (s, 1H), 8.69 (d, J=3.8 Hz, 1H), 8.02 (s, 1H), 8.01 (d, J=7.5 Hz, 1H), 7.63 (d, J=1.6 Hz, 1H), 7.40 (dd, J=7.6, 4.0 Hz, 1H), 7.13 (s, 1H), 6.53 (d, J=1.6 Hz, 1H), 5.30 (s, 2H), 5.28 (s, 2H), 4.12 (q, J=7.1 Hz, 2H), 3.93 (s, 3H), 1.18 (t, J=7.1 Hz, 3H). LRMS (M+H+) m/z 397.1.

References: [1]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0340.
[2]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0630; 0631.

47
[ 867267-28-5 ]
methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate hydrochloride [ No CAS ]
methyl 3-(3-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	Step 5 ;A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (30 mg, 0.20 mmol, 1 eq.), methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate hydrochloride (63 mg, 0.20 mmol, 1 eq.), and K2CO3 (100 mg, 10.32 mmol, 4 eq.) in DMF (5.0 mL) was heated at 70 C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give methyl 3-(3-(3-((4-formyl-6-methoxypyridin-3-yloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate (88 mg, quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.50 (s, 1H), 8.65 (dd, J=4.7, 0.9 Hz, 1H), 8.09 (s, 1H), 8.02 (dd, J=7.8, 0.8 Hz, 1H), 7.53 (d, J=2.3 Hz, 1H), 7.31 (dd, J=7.9, 4.8 Hz, 1H), 7.12 (s, 1H), 6.96 (d, J=2.3 Hz, 1H), 5.71 (s, 2H), 4.46 (t, J=6.6 Hz, 2H), 3.93 (s, 3H), 3.69 (s, 3H), 2.91 (t, J=6.6 Hz, 2H). LRMS (M+H+) m/z 397.1.
88 mg	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 2h;	[0349] A mixture of <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (30 mg, 0.20 mmol, 1 eq.), methyl 3-(3-(3-(chloromethyl)pyridin-2-yl)-lH-pyrazol-l-yl)propanoate hydrochloride (63 mg, 0.20 mmol, 1 eq.), and K2C03(100 mg, 10.32 mmol, 4 eq.) in DMF (5.0 mL) was heated at 70 C for 2 h. The mixture was cooled, filtered, concentrated, and purified on silica gel using a mixture of EtOAc and hexanes as eluent to give methyl 3-(3-(3-((4-formyI-6-methoxypyridin-3- yloxy)methyl)pyridin-2-yl)-lH-pyrazol-l-yl)propanoate (88 mg, quantitative yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 10.50 (s, 1H), 8.65 (dd, J= 4.7, 0.9 Hz, 1H), 8.09 (s, 1H), 8.02 (dd, J= 7.8, 0.8 Hz, 1H), 7.53 (d, J= 2.3 Hz, 1H), 7.31 (dd, J = 7.9, 4.8 Hz, lH), 7.12 (s, 1H), 6.96 (d,J= 2.3 Hz, 1H), 5.71 (s, 2H), 4.46 (t, J= 6.6 Hz, 2H), 3.93 (s, 3H), 3.69 (s, 3H), 2.91 (t, J= 6.6 Hz, 2H). LRMS (M+H+) m/z 397.1.

References: [1]Patent: US2015/344483,2015,A1 .Location in patent: Paragraph 0645; 0646.
[2]Patent: WO2013/102145,2013,A1 .Location in patent: Paragraph 0349.

48
[ 867267-28-5 ]
5-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)-2-oxo-1,2-dihydropyridine-4-carbaldehyde [ No CAS ]

References: [1]Patent: US2014/275152,2014,A1 .

49
[ 867267-28-5 ]
tert-butyl 4-(bromomethyl)-5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
tert-butyl 4-(((4-formyl-6-methoxypyridin-3-yl)oxy)methyl)-5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Step 5: To a solution of tert-butyl 4-(bromomethyl)-5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydropyridine-1(2H)-carboxylate (18 mg, 0.05 mmol) and <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (10 mg, 0.06 mmol) in DMF (1 mL) was added K2CO3 (14 mg, 0.1 mmol). After stirred at room temperature for 1 h, it was diluted with water and EtOAc, organic layer was separated, and the aqueous layer was extracted with EtOAc, organic layer was combined, washed with brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=2:1) to give tert-butyl 4-(((4-formyl-6-methoxypyridin-3-yl)oxy)methyl)-3-(1-isopropyl-1H-pyrazol-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (7.2 mg). 1H NMR (400 MHz, CDCl3) (ppm) 10.39 (s, 1H), 7.79 (s, 1H), 7.56 (d, J=1.6 Hz, 1H), 7.05 (s, 1H), 6.11 (d, J=1.6 Hz, 1H), 4.40 (s, 2H), 4.38 (m, 1H), 4.01 (s, 2H), 3.88 (s, 3H), 3.66 (bs, 2H), 2.46 (bs, 2H), 1.48 (s, 9H), 1.43 (d, 6.4 Hz, 6H). MS (ESI) m/z 457.3 [M+H]+.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

50
[ 867267-28-5 ]
5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole [ No CAS ]
2-methoxy-5-[[5-(2-propan-2-ylpyrazol-3-yl)-3,6-dihydro-2H-pyran-4-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	GBT863 Preparation of 2-methoxy-5-[[5-(2-propan-2-ylpyrazol-3-yl)-3,6-dihydro-2H-pyran-4-yl]methoxy]pyridine-4-carbaldehyde To a solution of 5-(4-(bromomethyl)-5,6-dihydro-2H-pyran-3-yl)-1-isopropyl-1H-pyrazole (50 mg, 0.19 mmol) (see the synthesis of GBT861) and <strong>[867267-28-5]5-hydroxy-2-methoxyisonicotinaldehyde</strong> (30 mg, 0.23 mmol) in DMF (1 mL) was added K2CO3 (50 mg, 0.38 mmol). After stirred at room temperature for 3 h, it was diluted with water and EtOAc, organic layer was separated, and the aqueous layer was extracted with EtOAc, organic layer was combined, washed with brine, dried and concentrated to give crude product, which was purified by column (Hexanes/EtOAc=1:1) to give 5-((5-(1-isopropyl-1H-pyrazol-5-yl)-3,6-dihydro-2H-pyran-4-yl)methoxy)-2-methoxyisonicotinaldehyde (26 mg). 1H NMR (400 MHz, CDCl3) δ (ppm) 10.40 (s, 1H), 7.81 (s, 1H), 7.54 (d, J=1.6 Hz, 1H), 7.05 (s, 1H), 6.08 (d, J=1.6 Hz, 1H), 4.42 (s, 2H), 4.40 (m, 1H), 4.19 (s, 2H), 3.98 (t, J=5.6 Hz, 2H), 3.88 (s, 3H), 2.47 (s, 2H), 1.41 (d, J=6.8 Hz, 6H); MS (ESI) m/z 358.4 [M+H]+.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

51
[ 867267-28-5 ]
3-(chloromethyl)-2-(2-methoxyphenyl)pyridine [ No CAS ]
2-methoxy-5-[[2-(2-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde bis(trifluoroacetic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	Step 3: Into a 100-mL round-bottom flask, was placed a solution of 3-(chloromethyl)-2-(2-methoxyphenyl)pyridine (306 mg, 1.31 mmol, 1.00 equiv) in CH3CN (20 mL). 5-Hydroxy-2-methoxypyridine-4-carbaldehyde (200 mg, 1.31 mmol, 1.00 equiv), potassium carbonate (364 mg, 2.63 mmol, 2.00 equiv), and KI (44 mg, 0.27 mmol, 0.20 equiv) were added to the reaction mixture. The resulting solution was stirred for 5 h at 60 C., and then it was concentrated under vacuum. The crude product (200 mg) was purified by Prep-HPLC with the following conditions (Prep-HPLC-010): Column, SunFire Prep C18 OBD Column, 5 um, 19*150 mm; mobile phase, water with 0.1% HCOOH and MeCN (10.0% MeCN up to 40.0% in 10 min, up to 95.0% in 2 min, down to 10.0% in 2 min); Detector, Waters 2545 UvDector 254 & 220 nm. This resulted in 65 mg (9%) of 2-methoxy-5-[[2-(2-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde bis(trifluoroacetic acid) as a yellow solid. The compound exhibited a melting point of 105-107 C. 1HNMR (300 MHz, CDCl3) δ 10.32 (s, 1H), 8.69 (s, 1H), 7.93 (m, 2H), 7.36 (m, 3H), 6.99 (m, 3H), 5.35 (s, 2H), 3.86 (m, 6H); MS (ESI) m/z 351 [M+Hr.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

52
[ 867267-28-5 ]
3-(chloromethyl)-2-(2-methoxyphenyl)pyridine [ No CAS ]
2-methoxy-5-[[2-(4-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; trifluoroacetic acid; In acetonitrile;	Step 3: Into a 50-mL round-bottom flask, was placed a solution of 3-(chloromethyl)-2-(2-methoxyphenyl)pyridine (234 mg, 1.00 mmol, 1.00 equiv), 5-hydroxy-2-methoxypyridine-4-carbaldehyde (153 mg, 1.00 mmol, 1.00 equiv), and potassium carbonate (278 mg, 2.01 mmol, 2.00 equiv) in CH3CN (20 mL). The resulting solution was stirred for 4 h at 70 C., and then it was concentrated under vacuum. The crude product (300 mg) was purified by Prep-HPLC with the following conditions (Prep-HPLC-010): Column, SunFire Prep C18 OBD Column, 5 um; 19*150 mm; mobile phase, water with 0.1% TFA and MeCN (20.0% MeCN up to 50.0% in 10 min, up to 95.0% in 2 min, down to 20.0% in 1 min); Detector, Waters 2545 UvDector 254 & 220 nm. This resulted in 265.1 mg (46%) of 2-methoxy-5-[[2-(4-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde; bis(trifluoroacetic acid) as a brown oil. 1HNMR (300 MHz, DMSO-d6) δ 10.08 (s, 1H), 8.69 (m, 1H), 8.15 (m, 2H), 7.50 (m, 1H), 7.37 (m, 1H), 7.18 (m, 2H), 7.16 (m, 1H), 6.99 (m, 1H), 5.34 (s, 2H), 3.86 (s, 3H), 3.77 (s, 3H); MS (ESI) mk 351 [M+H]+.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

53
[ 867267-28-5 ]
3-(chloromethyl)-2-(3-methoxyphenyl)pyridine [ No CAS ]
2-methoxy-5-[[2-(3-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde bis(trifluoroacetic acid) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; trifluoroacetic acid; In acetonitrile;	Step 3: Into a 100-mL round-bottom flask, was placed a solution of 3-(chloromethyl)-2-(3-methoxyphenyl)pyridine (234 mg, 1.00 mmol, 1.00 equiv), 5-hydroxy-2-methoxypyridine-4-carbaldehyde (153 mg, 1.00 mmol, 1.00 equiv), and potassium carbonate (278 mg, 2.01 mmol, 2.00 equiv) in CH3CN (30 mL). The resulting solution was stirred for 4 h at 70 C., and then it was concentrated under vacuum. The crude product (200 mg) was purified by Prep-HPLC with the following conditions (Prep-HPLC-010): Column, SunFire Prep C18 OBD Column, 5 um, 19*150 mm; mobile phase, water with 0.1% TFA and MeCN (20% MeCN up to 40% in 10 min, up to 95% in 2 min, down to 20% in 1 min); Detector, Waters 2545 UvDector 254 & 220 nm. This resulted in 100.8 mg (17%) of 2-methoxy-5-[[2-(3-methoxyphenyl)pyridin-3-yl]methoxy]pyridine-4-carbaldehyde bis(trifluoroacetic acid) as a yellow solid. 1HNMR (300 MHz, DMSO-d6) δ 10.01 (s, 1H), 8.65 (m, 1H), 8.39 (s, 1H), 8.10 (m, 2H), 7.57 (d, J=9 Hz, 2H), 7.42 (m, 1H), 6.97 (m, 3H), 5.33 (s, 2H) 3.80 (m, 6H); MS (ESI) m/z 351 [M+H]+.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

54
[ 867267-28-5 ]
3-(chloromethyl)-2-(2-chlorophenyl)pyridine [ No CAS ]
5-[[2-(2-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	Step 3: Into a 50-mL round-bottom flask, was placed a solution of 3-(chloromethyl)-2-(2-chlorophenyl)pyridine (309 mg, 1.30 mmol, 1.00 equiv), 5-hydroxy-2-methoxypyridine-4-carbaldehyde (200 mg, 1.31 mmol, 1.00 equiv), and potassium carbonate (361 mg, 2.61 mmol, 1.50 equiv) in CH3CN. (20 mL). The resulting solution was stirred for 4 h at 70 C., and then it was concentrated under vacuum. The residue was purified by prep-HPLC. This resulted in 86.2 mg (11%) of 5-[[2-(2-chlorophenyl)pyridin-3-yl]methoxy]-2-methoxypyridine-4-carbaldehyde; bis(trifluoroacetic acid) as a brown oil. 1HNMR (300 MHz, DMSO-d6) δ 10.06 (s, 1H), 8.69 (m, 1H), 8.19 (m, 1H), 8.05 (s, 1H), 7.56 (m, 2H), 7.41 (m, 3H), 6.92 (s, 1H), 5.14 (m, 2H), 3.81 (s, 3H); MS (ESI) m/z 355 [M+H]+.

References: [1]Patent: US2014/275152,2014,A1 .Location in patent: Page/Page column.

Historical Records

Technical Information

• Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Ethers • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 867267-28-5 ]

Aldehydes

A604609 [867267-25-2]

2,5-Dimethoxyisonicotinaldehyde

Similarity: 0.98

A219234 [867267-26-3]

2,5-Dimethoxynicotinaldehyde

Similarity: 0.86

A497733 [141580-71-4]

2-(Pyridin-2-yloxy)benzaldehyde

Similarity: 0.85

A284636 [1849-52-1]

3-Methoxyisonicotinaldehyde

Similarity: 0.83

A160818 [72716-87-1]

2-Methoxyisonicotinaldehyde

Similarity: 0.82

Ethers

A604609 [867267-25-2]

2,5-Dimethoxyisonicotinaldehyde

Similarity: 0.98

A528093 [1086389-80-1]

6-Methoxy-4-methylpyridin-3-ol

Similarity: 0.88

A219234 [867267-26-3]

2,5-Dimethoxynicotinaldehyde

Similarity: 0.86

A497733 [141580-71-4]

2-(Pyridin-2-yloxy)benzaldehyde

Similarity: 0.85

A284636 [1849-52-1]

3-Methoxyisonicotinaldehyde

Similarity: 0.83

Alcohols

A528093 [1086389-80-1]

6-Methoxy-4-methylpyridin-3-ol

Similarity: 0.88

A153590 [1227580-14-4]

2-Methoxy-4-methylpyridin-3-ol

Similarity: 0.82

Related Parent Nucleus of
[ 867267-28-5 ]

Pyridines

A604609 [867267-25-2]

2,5-Dimethoxyisonicotinaldehyde

Similarity: 0.98

A528093 [1086389-80-1]

6-Methoxy-4-methylpyridin-3-ol

Similarity: 0.88

A219234 [867267-26-3]

2,5-Dimethoxynicotinaldehyde

Similarity: 0.86

A497733 [141580-71-4]

2-(Pyridin-2-yloxy)benzaldehyde

Similarity: 0.85

A284636 [1849-52-1]

3-Methoxyisonicotinaldehyde

Similarity: 0.83

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P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
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H200	Unstable explosive
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Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 867267-28-5

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CAS No.: 867267-28-5

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[ 867267-28-5 ]

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Safety of [ 867267-28-5 ]

Application In Synthesis of [ 867267-28-5 ]

[ 867267-28-5 ] Synthesis Path-Downstream 1~54

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