1309774-03-5|7-Bromo-2-chloro-1,5-naphthyridine| Ambeed

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Quality Control of [ 1309774-03-5 ] Purity: 95% SDS Specification

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Product Details of [ 1309774-03-5 ]

CAS No. :	1309774-03-5
Formula :	C₈H₄BrClN₂
M.W :	243.49
SMILES Code :	ClC1=NC2=CC(Br)=CN=C2C=C1
MDL No. :	MFCD24848136
InChI Key :	GPFKNUQKQAMKLP-UHFFFAOYSA-N
Pubchem ID :	58310544

Safety of [ 1309774-03-5 ]

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

Application In Synthesis of [ 1309774-03-5 ]

* 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 [ 1309774-03-5 ]

[ 1309774-03-5 ] Synthesis Path-Downstream 1~35

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References: [1]Patent: WO2011/64250,2011,A1 .
[2]Patent: EP2332939,2011,A1 .
[3]Patent: WO2011/149937,2011,A1 .
[4]Patent: WO2013/78441,2013,A1 .
[5]Patent: WO2014/151147,2014,A1 .
[6]Patent: US2015/30588,2015,A1 .
[7]Patent: US9295673,2016,B2 .

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Yield	Reaction Conditions	Operation in experiment
22%; 48%		Example 2.1.1 and Example 2.1.2: 7-Bromo-2-chloro-[1 ,5]naphthyridine and 7- Bromo-4-chloro-[1 ,5]naphthyridine7.97 g (35.4 mmol, 1 eq) of 3-bromo-1 ,5-naphthyridine-5-oxide and 9.9 ml. (106.2 mmol, 3 eq) of phosphorus oxychloride were introduced in 600 ml. of methylene chloride. The mixture was stirred at reflux for 18 h. Methylene chloride was evaporated in part (3/4). 1 M aqueous NaOH solution was added carefully at 0 C. Aqueous layer was extracted with methylene chloride. Organic layers were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride as eluent. The solvent was evaporated to dryness to afford 1 .97 g of 7-bromo-2-chloro-1 ,5-naphthyridine (white powder) with 22% yield and 4.16 g of 7- bromo-4-chloro-1 ,5-naphthyridine (white powder) with 48% yield. 7-Bromo-2-chloro-[1 ,5]naphthyridineYield: 1.97 g (22 % of theory), m.p.: 168-169 C.1H-NMR (DMSO-d6, 400 MHz): = 9, 15 (d, 1 H); 8,79 (d, 1 H); 8,55 (d, 1 H); 7,93 (d, 1 H) ppm.MS: m/z 245 (M+H+).7-Bromo-4-chloro-[1 ,5]naphthyridineYield: 4.16 g (48 % of theory). m.p.: 162-163 C.1H-NMR (DMSO-d6, 400 MHz): delta = 9,22 (d, 1 H); 8,99 (d, 1 H); 8,88 (d, 1 H); 8, 1 1 (d, 1 H) ppm. MS: m/z 245 (M+H+).
22%; 48%		Example 2.1.1 and Example 2.1.2: 7-Bromo-2-chloro-[1,5]naphthyridine and 7-Bromo-4-chloro-[1,5]naphthyridine [Show Image] [Show Image] 7.97 g (35.4 mmol, 1 eq) of 3-bromo-1,5-naphthyridine-5-oxide and 9.9 mL (106.2 mmol, 3 eq) of phosphorus oxychloride were introduced in 600 mL of methylene chloride. The mixture was stirred at reflux for 18 h. Methylene chloride was evaporated in part (3/4). 1M aqueous NaOH solution was added carefully at 0 C. Aqueous layer was extracted with methylene chloride. Organic layers were dried over Na2SO4, filtered and evaporated to dryness.The residue was purified by column chromatography using methylene chloride as eluent. The solvent was evaporated to dryness to afford 1.97 g of 7-bromo-2-chloro-1,5-naphthyridine (white powder) with 22% yield and 4.16 g of 7-bromo-4-chloro-1,5-naphthyridine (white powder) with 48% yield.7-Bromo-2-chloro-[1,5]naphthyridine Yield: 1.97 g (22 % of theory). m.p.: 168-169 C. 1H-NMR (DMSO-d6, 400 MHz); = 9,15 (d, 1H); 8,79 (d, 1H); 8,55 (d, 1H); 7,93 (d, 1H) ppm. MS: m/z 245 (M+H+).7-Bromo-4-chloro-[1,5]naphthyridine Yield: 4.16 g (48 % of theory). m.p.: 162-163 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 9,22 (d, 1H); 8,99 (d, 1H); 8,88 (d, 1H); 8,11 (d, 1H) ppm. MS: m/z 245 (M+H+).

References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3748 - 3752.
[3]Patent: WO2011/64250,2011,A1 .Location in patent: Page/Page column 22-23.
[4]Patent: EP2332939,2011,A1 .Location in patent: Page/Page column 14.

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Yield	Reaction Conditions	Operation in experiment
85%	With ammonium hydroxide; In 1,4-dioxane; at 140℃; for 24h;Sealed tube;	In a sealed tube, a mixture of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> 4b (2.50 g, 10.3 mmol) and 28% aqueous ammonia solution (60 mL) in dioxane (60 mL) was heated at 140 C for 24 h. Then, the reaction mixture was allowed to cool at room temperature and water was added. The aqueous layer was extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtrated and the solvent was removed under reduced pressure. The crude mixture was purified by column chromatography on silica gel eluting with dichloromethane, then dichloromethane/ethanol 98:2 to give compound 5 as a white solid (1.95 g, 85%); Rf=0.39 (CH2Cl2/EtOH, 96:4); mp: 168-169 C; 1H NMR (400 MHz, [D6]DMSO): delta=8.57 (d, J=2.1 Hz, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.96 (d, J=9.1 Hz, 1H), 6.98 (br s, 2H), 6.04 (d, J=9.1 Hz, 1H); 13C NMR (100 MHz, [D6]DMSO): delta= 159.1, 145.1, 144.2, 138.6, 137.7, 133.8, 119.6, 116.9; MS (ESI) m/z (%): 224.0 (100) [M+H]+, 226.1 (100) [M+H+2]+.
80%	With ammonia; In 1,4-dioxane; water; at 160℃; for 24h;Sealed reactor;	Example 3.1 : 7-Bromo-[1 ,5]naphthyridin-2-ylamineIn a sealed reactor, 500 mg (1 .23 mmol, 1 eq) of 7-bromo-2-chloro-1 ,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2S04, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C.1H-NMR (DMSO-d6, 400 MHz): delta = 8,57 (d, 1 H); 8,05 (d, 1 H); 7,96 (d, 1 H); 6,04 (d, 1 H); 6,98 (s, 2H) ppm.MS: m/z 225 (M+H+).
80%	With ammonia; In 1,4-dioxane; water; at 160℃; for 24h;Sealed reactor;	Example 3.1: 7-Bromo-[1,5]naphthyridin-2-ylamine [Show Image] In a sealed reactor, 500 mg (1.23 mmol, 1 eq) of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 8,57 (d, 1H); 8,05 (d, 1H); 7,96 (d, 1H); 6,04 (d, 1H); 6,98 (s, 2H) ppm. MS: m/z 225 (M+H+).

90 mg	With ammonium hydroxide; In 1,4-dioxane; water; at 120℃; for 3h;Microwave irradiation;	A mixed solution of the compound 0001-3 (100 mg) in 1,4-dioxane (2 ml) and a 25% aqueous ammonia solution was stirred at 120C for 3 hours using a microwave reaction device. The reaction solution was cooled, and brine and ethyl acetate were added thereto. The organic layer was separated and then dried over sodium sulfate. The solvent was evaporated under reduced pressure to obtain a 0001-4 (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.02 (1H, d), 7.92 (1H, d), 7.01 (1H, d), 6.94 (1H, s). MS m/z (M+H): 224,226.
90 mg	With ammonium hydroxide; In 1,4-dioxane; at 120℃; for 3h;Microwave irradiation;	0031-1 A mixture solution of <strong>[1309774-03-5]7-bromo-2-chloro-1,5-naphthyridine</strong> (100 mg) in 1,4-dioxane (2 mL) and a 25% ammonia aqueous solution was stirred at 120 C. for 3 hours using a microwave reaction apparatus. The reaction mixture was cooled to room temperature, and a saturated sodium chloride aqueous solution and ethyl acetate were added thereto. The organic layer was collected by separation, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 7-bromo-1,5-naphthyridine-2-amine (90 mg) as a white solid. 1H-NMR (DMSO-d6) delta: 8.53 (1H, d), 8.0 (1H, d), 7.9 (1H, d), 7.0 (1H, d), 6.9 (1H, s). MS m/z (M+H): 224, 226.

References: [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3748 - 3752.
[2]Patent: WO2011/64250,2011,A1 .Location in patent: Page/Page column 23-24.
[3]Patent: EP2332939,2011,A1 .Location in patent: Page/Page column 15.
[4]Patent: EP2727920,2014,A1 .Location in patent: Paragraph 0269-0270.
[5]Patent: US2015/322063,2015,A1 .Location in patent: Paragraph 0603; 0604; 0605; 0606; 1079; 1080; 1081.

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References: [1]Patent: WO2011/64250,2011,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3748 - 3752.

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References: [1]Patent: WO2011/64250,2011,A1 .
[2]Patent: EP2332939,2011,A1 .
[3]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3748 - 3752.

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References: [1]Patent: WO2011/64250,2011,A1 .

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References: [1]Patent: WO2011/64250,2011,A1 .

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References: [1]Patent: WO2011/64250,2011,A1 .

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Yield	Reaction Conditions	Operation in experiment
74.7%	at 140℃;sealed tube;	A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino-l,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]
74.7%	at 140℃;Sealed tube;	Example 4b: Synthesis of 7-bromo-2-morpholino-l,5-naphthyridine F-32) [00336] A mixture of 7-bromo-2-chloro-l,5-naphthyridine (F-31) (200 mg, 0.82 mmol, 1.0 eq) and morpholine (10 mL) was stirred in a sealed-tube at 140 C overnight. The reaction mixture was cooled to RT, diluted with ethyl acetate (150 mL) and then washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-morpholino- 1,5-naphthyridine (F-32) (180 mg, 74.7% yield). ESI-MS m/z : 294.01 [M+H]+.

References: [1]Patent: WO2011/149937,2011,A1 .Location in patent: Page/Page column 41; 87.
[2]Patent: WO2013/78441,2013,A1 .Location in patent: Paragraph 00143; 00336.
[3]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641.
[4]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 66.
[5]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 342; 343.

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References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

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References: [1]Patent: WO2011/149937,2011,A1 .
[2]Patent: WO2013/78441,2013,A1 .
[3]Patent: WO2014/151147,2014,A1 .
[4]Patent: US2015/30588,2015,A1 .
[5]Patent: US9295673,2016,B2 .

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Yield	Reaction Conditions	Operation in experiment
62.9%		7-bromo-l,5-naphthyridin-2(lH)-one (C-4) (3.1 g, 13.78 mmol, 1.0 eq) was dissolved in POCl3 (20 mL) and the resulting mixture was stirred at reflux for lh. The reaction was complete based on TLC analysis. The mixture was concentrated in vacuo to remove POCI3. The residue was poured into ice water (30 mL) and neutralized with saturated aqueous Na2C03 solution to adjust the pH value to 7-8 while keeping the temperature below 10 C. The resulting mixture was extracted with ethyl acetate (3 x 30 mL), the combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo- 2-chloro-l,5-naphthyridine (F-31) (2.11 g, 62.9% yield). ESI-MS m/z : 242.9 [M+H]+.
62.9%	With trichlorophosphate; for 1h;Reflux;	Example 4a: Synthesis of 7-bromo-2-chloro-l,5-naphthyridine (F-31) [00335] 7-bromo-l,5-naphthyridin-2(lH)-one (C-4) (3.1 g, 13.78 mmol, 1.0 eq) was dissolved in POCI3 (20 mL) and the resulting mixture was stirred at reflux for lh. The reaction was complete based on TLC analysis. The mixture was concentrated in vacuo to remove POCI3. The residue was poured into ice water (30 mL) and neutralized with saturated aqueous Na2C03 solution to adjust the pH value to 7-8 while keeping the temperature below 10 C. The resulting mixture was extracted with ethyl acetate (3 x 30 mL), the combined organic layer was washed with brine, dried over Na2S04 and filtered. The filtrate was concentrated in vacuo to afford the desired product 7-bromo-2-chloro-l,5- naphthyridine (F-31) (2.11 g, 62.9% yield). ESI-MS m/z : 242.9 [M+H]+.

References: [1]Patent: WO2011/149937,2011,A1 .Location in patent: Page/Page column 41; 87.
[2]Patent: WO2013/78441,2013,A1 .Location in patent: Paragraph 00143; 00335.
[3]Patent: WO2014/151147,2014,A1 .Location in patent: Paragraph 00641.
[4]Patent: US2015/30588,2015,A1 .Location in patent: Page/Page column 66.
[5]Patent: US9295673,2016,B2 .Location in patent: Page/Page column 342.

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References: [1]Patent: WO2013/78441,2013,A1 .
[2]Patent: WO2014/151147,2014,A1 .
[3]Patent: US2015/30588,2015,A1 .
[4]Patent: US9295673,2016,B2 .

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References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.

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References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.

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References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.

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References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.

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References: [1]ChemMedChem,2014,vol. 9,p. 217 - 232.

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