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Quality Control of 7-Azaindazole Purity: 97% SDS Specification

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NMR

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Product Details of 7-Azaindazole

CAS No. :	271-73-8
Formula :	C₆H₅N₃
M.W :	119.12
SMILES Code :	C12=NC=CC=C1C=NN2
MDL No. :	MFCD05663981
Boiling Point :	No data available
InChI Key :	GVLRTOYGRNLSDW-UHFFFAOYSA-N
Pubchem ID :	2755850

Safety of 7-Azaindazole

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 7-Azaindazole

* 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 [ 271-73-8 ]

[ 271-73-8 ] Synthesis Path-Downstream 1~35

1
[ 36404-88-3 ]
[ 116854-97-8 ]
[ 271-73-8 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 420-428.

2
[ 100-14-1 ]
[ 271-73-8 ]
[ 619-93-2 ]
[ 75427-18-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 938 - 942.

3
[ 70-34-8 ]
[ 271-73-8 ]
[ 116855-11-9 ]
[ 116855-12-0 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 420-428.

4
[ 100-44-7 ]
[ 271-73-8 ]
[ 116855-10-8 ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 12300 - 12306.
[2]Canadian Journal of Chemistry,1988,vol. 66,p. 420-428.

5
[ 4330-21-6 ]
[ 271-73-8 ]
[ 119368-13-7 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 945 - 951.

6
[ 75427-06-4 ]
[ 271-73-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 938 - 942.

7
[ 77287-34-4 ]
[ 271-73-8 ]
[ 116855-16-4 ]

References: [1]Canadian Journal of Chemistry,1988,vol. 66,p. 420-428.

8
[ 75427-09-7 ]
[ 271-73-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 938 - 942.

9
[ 271-73-8 ]
[ 117007-52-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide; water; iodine; In 1,4-dioxane; at 55℃;	lEta-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> Compound 4a (0.50 g, 4.2 mmol), iodine (2.1 g, 8.3 mmol), 3M aqueous NaOH (20 mL) and 1,4-dioxane (20 mL) were added to a flask and the mixture was heated to 55 0C overnight. The organic solvent was removed in vacuo and acetic acid was added dropwise to adjust the solution pH to 5. A yellow solid was . precipitated, 'cqllected by filtration and air-dried to afford Compound 4b (0.93 g, 90percent). 1H NMR (400 MHz, CDCl3) delta 13.80 (br, s, 1 H), 8.66 (d, J = 4.8 Hz, IH), 7.88 (d, / = 7.2 Hz, IH), 7.26 (dd, /= 7.2, 4.8 Hz, IH); MS (ESI) m/z: 246 (M+H)+.
84%		To a solution of 1 H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> (I-6) (4 g, 34 mmol) in DMF (150 mL) was added KOH (7.6 g, 136 mmol) at 0 °C. The mixture was stirred at room temperature for 30 min. To the resulting mixture was added iodine (15 g, 61 mmol) in portions at 0°C and the mixture was stirred at room temperature overnight. TLC (petroleum ether/ EtOAc = 1 :1) showed the reaction was complete. The reaction mixture was poured into ice water and extracted with CH2CI2 (300 mL x 2). The combined organic layers were washed with sat. aq.Na2S03 (300 mL chi 2), brine (200 mL x 3), dried over Na2S04 and concentrated in vacuo to give 3-iodo-1 H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> (I-7) (7 g, 84percent) as a yellow solid.
	With potassium hydroxide; iodine; In N,N-dimethyl-formamide; at 20℃; for 1h;	Step 2: 3-iodo-<strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> (49-3); A solution of 1.00 g (8.40 mmol) of <strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> in 15 mL of DMF was treated with 4.26 g (16.80 mmol) of iodine, followed by 1.77 g (31.50 mmol) of solid KOH. The resulting reddish-brown mixture was stirred at ambient temperature for 1 hour. The reaction was diluted with 5.x. its volume with a solution of aq. 10percent NaHSO3, and the mixture stirred. The yellow solid precipitate was filtered off, washed with water, and dried in vacuo to give the desired product. The crude product was used as is in the next reaction. MS M+1=246.

	With N-iodo-succinimide; In acetonitrile; at 75℃; for 18.5h;Inert atmosphere;	A solution of the intermediate from Step A above (14.3g, 120mmol) and iV-iodosuccinimide (28.4g, 126mmoI) in acetonitrile (210 mL) was heated at 75 °C. After 17 hours, N- iodosuccinimide (5.4g, 24mmol) was added and the reaction solution stirred at 75 °C for an additional 1.5 hours. The reaction solution was cooled to room temperature and diluted with water. The slurry was concentrated in vacuo to remove most of the acetonitrile. The solid was collected, washed with water, and dried under a vacuum with a nitrogen sweep for 17 hours to give the title compound. NMR (400 MHz, CH CN-d3): delta 11.85 (s, 1 H); 8.55 (dd, J = 4.53,1.53 Hz, 1 H); 7.87 (dd, J = 8.1 1, 1.53 Hz, 1 H); 7.24 (dd, J = 8.1 1, 4.51 Hz, 1 H). m/z = 246.1 (M+H).
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 1h;Cooling with ice;	(2); Compound 2 (12.2 g) was dissolved in DMF (200 ml), and then thereto was added potassium hydroxide (26.86 g) with stirring under ice-cooling, then added gradually iodine (52.24 g), and then the mixture was warmed slowly to room temperature, and stirred at room temperature for an hour. The reaction mixture was poured into 10percent aqueous sodium hydrogen sulfite solution (1 L), and the precipitated crystals were filtered, washed with water, and then dried to give Compound 3 (21.07 g) as pale yellow crystals.MS (APCI) 246 [M+H]+
	With iodine; potassium hydroxide; In N,N-dimethyl-formamide; at 20℃; for 16h;	A. 3-lodo-I H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong>To a solution of iH-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> (2.00 g, i6.8 mmol) in DMF (35 mL) were added iodine (6.39 g, 25.2 mmol) and potassium hydroxide (2.35 g, 42.0 mmol). The reaction mixture was stirred at RT for i6 h. The mixture was diluted with iOpercent sodium thiosulfate and water and the resulting suspension was filtered to give the title compound as a yellow powder. TLC, R (EtOAc) = 0.8; MS (UPLCMS): 246.0 [M+H]+, 243.9 [M-H]-; tR (HPLC conditions f): i .3i mm.
	With N-iodo-succinimide; In acetonitrile; at 75℃; for 17h;	Compound (M-1) (100 mg, 0.839 mmol) was dissolved in acetonitrile (2.8 mL), NIS (208 mg, 0.923 mmol) wasadded and the mixture was stirred at 75°C for 17 hr. The reaction mixture was allowed to cool, ethyl acetate was added,and the mixture was successively washed with water and saturated brine, dried over anhydrous sodium sulfate, andfiltered. The solvent was evaporated under reduced pressure to give compound (M-2)
	With N-iodo-succinimide; In acetonitrile; at 75℃; for 17h;	Compound (M-1) (100 mg, 0.839 mmol) was dissolved in acetonitrile (2.8 mL)NIS (208 mg, 0.923 mmol) was added,And the mixture was stirred at 75 ° C. for 17 hours.The reaction solution was allowed to cool, ethyl acetate was added, water,And then washed successively with saturated brine,After drying with anhydrous sodium sulfate, filtration was carried out.By distilling off the solvent under reduced pressure,To obtain a compound (M-2).

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[2]Patent: WO2006/130673,2006,A1 .Location in patent: Page/Page column 86.
[3]European Journal of Medicinal Chemistry,2013,vol. 68,p. 361 - 371.
[4]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4763 - 4772.
[5]Patent: WO2016/97918,2016,A1 .Location in patent: Page/Page column 51-52.
[6]Patent: US2007/21442,2007,A1 .Location in patent: Page/Page column 56.
[7]Journal of Medicinal Chemistry,2010,vol. 53,p. 8368 - 8375.
[8]Patent: WO2011/149921,2011,A1 .Location in patent: Page/Page column 98.
[9]Patent: US2012/16117,2012,A1 .Location in patent: Page/Page column 28.
[10]Patent: WO2014/2057,2014,A1 .Location in patent: Page/Page column 52.
[11]Patent: EP3351533,2018,A1 .Location in patent: Paragraph 0201; 0202.
[12]Patent: JP2018/145180,2018,A .Location in patent: Paragraph 0210; 0211; 0212.

10
[ 271-73-8 ]
[ 1001413-89-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; Iodine monochloride; In dichloromethane; at 0℃; for 0.833333h;	lH-Pyrazolo[3,4-b]pyridine (0.225 g, 0.00189 mol) was dissolved in pyridine (2.0 mL, 0.025 mol; Acros) and cooled in an ice bath. A solution of 1.00 M of iodine monochloride in methylene chloride (2.1 mL; Aldrich) was added over 5 min. After 15 min the cooling bath was removed, and after another 30 min the solution was diluted with 200 mL of ethyl acetate. The organic solution was washed sequentially with 1 N hydrogen chloride and 1 N sodium hydroxide, dried over magnesium sulfate, and concentrated. The residue was taken up in DMF and purified by preparative HPLC to yield the desired product as TFA salt in 55.5 mg yield (8percent). MS m/z = 245.87 (M+l). IH NMR (400 MHz, DMSO-d6) .(TM). ppm 14.070 (s(br), IH) 8.564 (dd, J= 4.5, 1.6Hz, IH) 7.917 (d, J=8.0Hz, IH) 7.253 (dd, J=8.1, 4.5Hz, IH).

References: [1]Patent: WO2008/5457,2008,A2 .Location in patent: Page/Page column 116.

11
[ 271-73-8 ]
[ 875781-18-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[2]Patent: WO2006/130673,2006,A1 .

12
[ 271-73-8 ]
tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.

13
[ 271-73-8 ]
[ 916326-33-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[3]Patent: WO2006/130673,2006,A1 .

14
[ 271-73-8 ]
[ 916326-31-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[2]Patent: WO2006/130673,2006,A1 .

15
[ 271-73-8 ]
[ 916326-32-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1243 - 1245.
[2]Patent: WO2006/130673,2006,A1 .

16
[ 271-73-8 ]
[ 916326-34-6 ]

17
[ 271-73-8 ]
4-[3-(1H-benzoimidazol-2-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-isoquinoline [ No CAS ]

18
[ 271-73-8 ]
[ 916326-35-7 ]

19
[ 271-73-8 ]
[ 119368-18-2 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 945 - 951.

20
[ 271-73-8 ]
[ 119368-26-2 ]

References: [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 945 - 951.

21
[ 75427-15-5 ]
[ 271-73-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 938 - 942.

22
[ 36404-88-3 ]
[ 271-73-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With toluene-4-sulfonic acid; hydrazine hydrate; at 130℃; for 3h;Inert atmosphere;	Hydrazine hydrate (10 mL) was added to a mixture of 2-chloro-3-formylpyridine 1 (5.00 g, 35 mmol) and p-TsOH (3.50 g, 18 mmol). The reaction mixture was stirred for 3 h at 130 °C. Upon cooling with cold water, the mixture was extracted with EtOAc. The combined organic extracts were dried over anhydrous MgSO4. After filtration, the solvent was removed in vacuum and gave compound 2 (3.65 g, 87percent) as a yellow solid; mp 88?90 °C(97-98 °C);34 FTIR (KBr) numax/cm-1 3450 (N-H), 3089, 3026 (C-H Ar), 2958, 2915 (C-H), 1606, 1588, 1509, 1470, 1429 (C=N, C=C); 1H NMR (300 MHz, CDCl3) delta/ppm 1.69 (s, 1H, N-H), 7.19 (dd, 1H, J 4.7 and 7.5, ArH, 5-H), 8.12 (s, 1H, ArH, 3-H), 8.15 (d, 1H, J 8.1, ArH, 4-H), 8.63 (d, 1H, J 4.5, ArH, 6-H).
62%		Preparation of 1H-pyrazolo[3,4-b]pyridine 2-Chloro-3-pyridinecarboxyaldehyde (1.0 g, 7.0 mmol) and p-toluenesulfonic acid monohydrate (700 mg) were dissolved in hydrazine monohydrate (1.4 mL, 28.0 mmol). The resulting mixture was heated at 120°C for 10 minutes in a sealed tube under irradiation with a macrowave of 100 watts. After cooled to room temperature, the mixture was neutralized with a saturated sodium bicarbonate aqueous solution and extracted with DCM (50 mL) three times. The organic layer was dried over anhydrous sodium sulfate. The concentrated residue was purified by silica gel (Fuji Silysia, BW300, 30 g, n-hexane: ethyl acetate = 1:1) to give 1H-pyrazolo[3,4-b]pyridine (513 mg, yield: 62percent). 1H-NMR (270MHz, CDCl3) delta (ppm): 7.16 (1H, dd, J=4.6, 8.1Hz), 8.08 (1H, d, J=2.0Hz), 8.10 (1H, d, J=1.5Hz), 8.60 (1H, d, J=4.6Hz) ESI (LC-MS positive mode) m/z 120 (M+H).
	With hydrazine; In ethanol; water; for 24h;Heating / reflux;	EXAMPLE 49; 3-Chloro-5-{2-chloro-5-[2-(1H-pyrazolo[3,4-b]pyridin-3-yl)ethyl]phenoxy}benzonitrile (49-9); Step 1: 1H-pyrazolo[3,4-b]pyridine (49-2) A mixture of 10.00 g (70.65 mmol) of 2-chloro-3-formylpyridine(49-1) in 225 mL of absolute ethanol/100 mL of hydrazine hydrate was heated at reflux for 24 hours. The reaction mixture was then cooled to room temperature and concentrated in vacuo to a brown oil-solid. The crude product was chromatographed over silica gel with 2.5percent methanol/chloroform to give the desired product as a yellow oil that slowly crystallized to a yellow solid. 1H NMR (CDCl3): 7.20(m,1H), 8.15(m,2H), 8.66 (dd,1H), 12.49 (br s, 1H).

	With hydrazine hydrate; In water; at 100℃; for 72h;Inert atmosphere;	A solution of 2-chloropyridine-3-carbaldehyde (20g, 141mmol) and hydrazine monohydrate(60percent in water, 1 13g, 2.1 mol) in 140 mL water was heated at 100 °C for 72 hours. The reaction mixture was cooled to room temperature and diluted with 200 mL of EtOAc. The aqueous layer was separated and extracted with EtOAc (3x). The combined organics were dried over MgS04, filtered and concentrated in vacuo to give a light orange solid which was crystallized from hexanes to give the title compound as an off-white solid. NMR (400 MHz, CH3CN-d3): delta11.56 (s, 1 H); 8.51 (dd, J = 4.52, 1.56 Hz, 1 H); 8.17 (dd, J = 8.05, 1.58 Hz, 1 H); 8.05 (s, 1H); 7.17 (dd, J = 8.05, 4.51 Hz, 1 H).
		Reference Example 1; (1); According to the method of Chemical Communications 293-294 (1966), to a mixture of Compound 1 (20.0 g) and p-toluenesulfonic acid monohydrate (15.6 g) was added slowly hydrazine monohydrate (26.6 ml) with stirring under ice-cooling. The mixture was heated to stir at 130° C. for 21 hours. The reaction mixture was let stand to cool, and then poured into 25percent aqueous potassium carbonate solution, and extracted with ethyl acetate. The extracted layer was combined, and dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate 2:1 to 1:1). The resulting solid was triturated by hexane-ethyl acetate (1:1) to give Compound 2 (12.27 g) as colorless powdery crystals.MS (APCI) 120 [M+H]+
4 g	With hydrazine; In ethanol; for 24h;Reflux;	A stirred solution of 2-chloronicotinaldehyde (I-5) (5.1 g, 36 mmol) in EtOH (100 mL) and NH2NH2 (85 percent in H20, 50 mL) was heated to reflux for 24 hr. TLC (petroleum ether/ EtOAc = 1 :1) showed the reaction was complete. The mixture was concentrated and separated between H20 (100 mL) and EtOAc (200 mL). The aqueous layer was extracted with EtOAc (100 mL x 2). The combined organic layers were washed with brine (100 mL), dried over Na2S04 and concentrated in vacuo to give 1 H-pyrazolo[3,4-b]pyridine (I-6) (4 g, 93percent) as a yellow solid.
	With toluene-4-sulfonic acid; hydrazine hydrate; at 130℃; for 16h;	To a solution of 2-chloropyridine-3-carbaldehyde (3.00 g, 21.19 mmol, 1.00 eq) in hydrazine; hydrate (6.36 g, 127.14 mmol, 6.18 mL, 6.00 eq) was added PTSA (1.82 g, 10.60 mmol, 0.50 eq). The mixture was stirred at 130 C for 16 h. It was concentrated. The residue was purified by column chromatography to afford the title compound (1.50 g, 11.33 mmol, 53.48percent yield, 90percent purity) as a white solid.

References: [1]European Journal of Medicinal Chemistry,2012,vol. 57,p. 311 - 322.
[2]Journal of Organic Chemistry,2017,vol. 82,p. 12300 - 12306.
[3]Journal of the Brazilian Chemical Society,2013,vol. 24,p. 1295 - 1306.
[4]Patent: EP1921078,2008,A1 .Location in patent: Page/Page column 32.
[5]Patent: US2007/21442,2007,A1 .Location in patent: Page/Page column 56.
[6]Patent: WO2011/149921,2011,A1 .Location in patent: Page/Page column 98.
[7]Patent: US2012/16117,2012,A1 .Location in patent: Page/Page column 28.
[8]Heteroatom Chemistry,2016,vol. 27,p. 3 - 11.
[9]Patent: WO2016/97918,2016,A1 .Location in patent: Page/Page column 51.
[10]Patent: WO2018/13867,2018,A1 .Location in patent: Paragraph 505.

23
[ 1072875-08-1 ]
[ 271-73-8 ]
[ 1072875-34-3 ]
[ 1072875-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 20℃;Product distribution / selectivity;	Example 36 3-(3-Chloro-2-methyl-phenyl)-1-(2-pyrazolo[3,4-b]pyridin-1-yl-acetyl)-imidazolidin-4-one A mixture of 1-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one (230 mg, 0.8 mmol, 1 eq), <strong>[271-73-8]1H-Pyrazolo[3,4-b]pyridine</strong> (96 mg, 0.8 mmol, 1 eq), Cesium carbonate (653 mg, 2.0 mmol, 2.5 eq) in DMF (6 ml) was stirred at room temperature overnight. It was diluted with ethyl acetate, washed with water and purified with HPLC to give the desired product. LCMS observed for (M+H)+: 370.1 Example 37; 3-(3-Chloro-2-methyl-phenyl)-1-(2-pyrazolo[3,4-b]pyridin-2-yl-acetyl)-imidazolidin-4-one; A mixture of 1-(2-Chloro-acetyl)-3-(3-chloro-2-methyl-phenyl)-imidazolidin-4-one (230 mg, 0.8 mmol, 1 eq), <strong>[271-73-8]1H-Pyrazolo[3,4-b]pyridine</strong> (96 mg, 0.8 mmol, 1 eq), Cesium carbonate (653 mg, 2.0 mmol, 2.5 eq) in DMF (6 ml) was stirred at room temperature overnight. It was diluted with ethyl acetate, washed with water and purified with HPLC to give the desired product. LCMS observed for (M+H)+: 370.1

References: [1]Patent: US2008/269280,2008,A1 .Location in patent: Page/Page column 28-29.

24
[ 76513-69-4 ]
[ 271-73-8 ]
[ 1021938-94-2 ]

Yield	Reaction Conditions	Operation in experiment
		l-(2-TrimethylsilanylethoxymethylV4,5,6,7-tetrahvdro-lH-pyrazolor3,4-b1pyridine To a solution of lH-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong> (380 mg, 3.2 mmol) in DMF (5 mL) was added NaH (60percent dispersion in mineral oil, 153 mg, 3.8 mmol). After stirring for 20 min, the mixture was heated with a heat gun and then allowed to cool to rt. SEM-Cl (647 muL, 3.8 mmol) was added dropwise and stirring continued for 2 h. The resulting mixture was partitioned between water and ethyl acetate. The organic layer was separated and concentrated, and the residue was purified by flash column chromatography (silica gel, eluting with 0-50percent ethyl acetate in hexanes) to provide l-(2-trimethylsilanylethoxymethyl)-lH-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong>, which was dissolved in ethanol (30 mL) and flushed with a nitrogen stream. Palladium on charcoal (5percent wet on carbon, -50 mg) was added and the mixture was placed under hydrogen (50 psi) for 2 days. The reaction mixture was filtered, and the filtrate was concentrated to provide the title compound: 1H NMR (500 MHz, CDCl3) delta 7.13 (s, IH), 5.24 (s, 2H), 3.68 (br, IH), 3.54 (t, J = 8.2 Hz, 2H), 3.28 (m, 2H), 2.51 (t, J = 6.1, 2H), 1.81 (m, 2H), 0.89 (t, J = 8.2 Hz, 2H), -0.01 (s, 9H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 2912 - 2915.
[2]Patent: WO2008/51405,2008,A1 .Location in patent: Page/Page column 74.

25
[ 271-73-8 ]
[ 937-14-4 ]
[ 924909-12-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethyl acetate; at 0 - 20℃; for 13h;	Preparation of <strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> 7N-oxide m-chlorobenzoate <strong>[271-73-8]1H-Pyrazolo[3,4-b]pyridine</strong> (1.0 g, 8.48 mmol) was dissolved in ethyl acetate (8.5 mL), and an ethyl acetate (8 mL) solution of m-CPBA (65percent, 2.8 g, 10.6 mmol) was dropwise added thereto under ice-cooling. The resulting mixture was stirred at room temperature for 13 hours. The precipitated solid was collected by filtration under reduced pressure, washed with ethyl acetate, and dried under reduced pressure to give <strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> 7N-oxide m-chlorobenzoate (1.25 g) containing m-chlorobenzoic acid in a molar ratio of 20percent (yield: 85percent).

References: [1]Patent: EP1921078,2008,A1 .Location in patent: Page/Page column 32.

26
[ 6752-16-5 ]
[ 271-73-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4763 - 4772.
[2]European Journal of Medicinal Chemistry,2013,vol. 68,p. 361 - 371.

27
[ 271-73-8 ]
[ 350-46-9 ]
[ 1330064-78-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 12; 1-Ethyl-3-[4-(1H-pyrazolo[3,4-b]pyridin-1-yl)phenyl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one 12a) 1-(4-nitrophenyl)-<strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> To a stirred solution of <strong>[271-73-8]1H-<strong>[271-73-8]pyrazolo[3,4-b]pyridine</strong></strong> (300 mg) in DMF (3.0 mL) was added sodium hydride (101 mg) (60percent in mineral oil) with ice-cooling. The mixture was stirred at room temperature for 30 min, and then 1-fluoro-4-nitrobenzene (355 mg) was added. After stirring at room temperature for 2 h, the mixture was warmed up to 50° C. The mixture was stirred at 50° C. for 12 h. Cesium carbonate (821 mg) was added and the mixture was stirred at 100° C. for 12 h, and treated with water and AcOEt. The insoluble material was filtered off. The organic layer was separated and the aqueous layer was extracted with AcOEt. The organic layer was combined, dried over MgSO4 and concentrated in vacuo. The residue was used for the next reaction.

References: [1]Patent: US2011/319394,2011,A1 .Location in patent: Page/Page column 63.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1989 - 1992.

28
[ 271-73-8 ]
[ 956010-88-1 ]