[ CAS No. 228251-24-9 ] 5-Bromo-2-chloronicotinaldehyde

Cat. No.: A109483

2D 3D

Structure of 228251-24-9 * Storage: Inert atmosphere,2-8°C

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Quality Control of [ 228251-24-9 ]

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Product Details of [ 228251-24-9 ]

CAS No. :	228251-24-9	MDL No. :	MFCD08689713
Formula :	C₆H₃BrClNO	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	YGPYNLZCNDPHTQ-UHFFFAOYSA-N
M.W :	220.45	Pubchem ID :	23090988
Synonyms :

Calculated chemistry of [ 228251-24-9 ] Expand+

Safety of [ 228251-24-9 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 228251-24-9 ]

* 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 [ 228251-24-9 ]

[ 228251-24-9 ] Synthesis Path-Downstream 1~20

1
[ 228251-24-9 ]
C₂₈H₂₆NO₂PS [ No CAS ]
6-carboethoxy-2-methyl-4-(2'Cl,5'Br-3'-pyridine)thieno<3,2-c>pyridine [ No CAS ]

Reference： [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1999,vol. 55,p. 1035 - 1048

2
[ 742100-61-4 ]
[ 228251-24-9 ]
[ 742100-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; dimethyl sulfoxide; at 80℃; for 3h;	Reference Example 164 A suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.5 g), 3,4-dimethylpyrrolidine hydrochloride (1.85 g) and sodium carbonate (1.8 g) in DMSO (45 ml) and water (22.5 ml) was stirred for 3 hours at 80C under a nitrogen atmosphere. After returning to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, which was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 19: 1 ? hexane: ethyl acetate = 4: 1). The resulting residue recrystallized from hexane-ethyl acetate to give 5-bromo-2-(3,4-dimethylpyrrolidin-1-yl)nicotinaldehyde (1.56 g) as yellow crystals. m.p. 98.5-99.5C. 1H-NMR (300 MHz, CDCl3) delta 0.98 (6H, d, J=6.6 Hz), 2.31-2.41 (2H, m), 3.22-3.28 (2H, m), 3.59-3.65 (2H, m), 8.00 (1H, d, J=2.4 Hz), 8.29 (1H, d, J=2.4 Hz), 9.95 (1H, s). Elementary analysis C12H15N2OBr, Calcd. C, 50.90; H, 5.34; N, 9.89: Found C, 50.93; H, 5.35; N, 9.82.

Reference： [1]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 100

3
[ 644971-22-2 ]
[ 228251-24-9 ]
[ 742100-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; dimethyl sulfoxide; at 75℃; for 2h;	Reference Example 159 A suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.5 g), 3-hydroxymethylpyrrolidine hydrochloride (1.87 g) and sodium carbonate (1.8 g) in DMSO (45 ml) and water (22.5 ml) was heated for 2 hours at 75C under a nitrogen atmosphere. After returning to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 2: 1 ? ethyl acetate). The resulting solids were washed with hexane to give 5-bromo-2-[3-(hydroxymethyl)pyrrolidin-1-yl]nicotinaldehyde (1.67 g) as yellow crystals. m.p. 84.0-85.5C. 1H-NMR (300 MHz, CDCl3) delta 1.47-1.60 (1H, m), 1.78-1.90 (1H, m), 2.08-2.20 (1H, m), 2.49-2.59 (1H, m), 3.42-3.74 (6H, m), 8.02 (1H, d, J=2.4 Hz), 8.32 (1H, d, J=2.4 Hz), 9.96 (1H, s). Elementary analysis C11H13N2O2Br, Calcd. C, 46.33; H, 4.60; N, 9.82: Found C, 46.50; H, 4.57; N, 9.74.

Reference： [1]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 99

4
[ 34375-89-8 ]
[ 228251-24-9 ]
[ 742100-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; dimethyl sulfoxide; at 75℃; for 2h;	Reference Example 155 A suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.2 g), 3-methylpyrrolidine (928 mg) and sodium carbonate (1.16 g) in DMSO (40 ml) and water (20 ml) was stirred for 2 hours at 75C under a nitrogen atmosphere. After returning to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was separated and purified by silica gel column chromatography (hexane: ethyl acetate = 20: 1 ? hexane: ethyl acetate = 4: 1). The resulting solids were washed with hexane to give 5-bromo-2-(3-methylpyrrolidin-1-yl)nicotinaldehyde (761 mg) as yellow crystals. m.p. 72.0-73.0C. 1H-NMR (300 MHz, CDCl3) delta 1.13 (3H, d, J=6.6 Hz), 1.53-1.67 (1H, m), 2.07-2.16 (1H, m), 2.28-2.41 (1H, m), 3.17-3.24 (1H, m), 3.46-3.56 (2H, m), 3.61-3.70 (1H, m), 8.01 (1H, d, J=2.4 Hz), 8.31 (1H, d, J=2.4 Hz), 9.96 (1H, s). Elementary analysis C11H13N2OBr, Calcd. C, 49.09; H, 4.87; N, 10.41: Found C, 49.07; H, 4.88; N, 10.29.

Reference： [1]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 98

5
[ 742100-75-0 ]
[ 228251-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridinium chlorochromate; In dichloromethane; at 18 - 25℃; for 2h;	(5-Bromo-2-chloropyridin-3-yl)methanol (Intermediate 3, 0.67 g, 3.01 mmol) and pyridinium chlorochromate (0.779 g, 3.61 mmol) were combined in anhydrous dichloromethane (10 ml) and stirred at room temperature. The reaction was stirred for 2 hours. The reaction mixture was diluted with diethyl ether and filtered. The filtrate was concentrated to a tan solid. The solid was suspended in methanol and deposited onto Isolute and dried. Purification by normal phase Isco column (40%- 100% dichloromethane/hexane) afforded the desired compound as a white solid(0.24g).MS (ES) MH+: 220 for C6H3BrClNO.1H NMR: 8.40 (s, IH), 8.85 (s, IH), 10.18 (s, IH)
		Reference Example 154 To a solution of oxalyl chloride (1.98 ml) in dichloromethane (20 ml) was added dropwise a solution of DMSO (3.45 ml) in dichloromethane (30 ml) at -78C under a nitrogen atmosphere. The mixture was stirred as such for 10 minutes, and then a solution of 5-bromo-2-chloropyridin-3-yl)methanol (3.6 g) in dichloromethane (35 ml) was added dropwise thereto. The mixture was stirred as such for 10 minutes, and then triethylamine (13.5 ml) was added dropwise thereto. After stirring as such for 10 minutes, the resulting mixture was returned to room temperature and stirred for 1 hour. To the reaction solution was added water, followed by separation. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 6: 1) to give 5-bromo-2-chloronicotinaldehyde (3.4 g) as colorless crystals. m.p. 88.0-89.0C. 1H-NMR (300 MHz, CDCl3) delta 8.33 (1H, d, J=2.7 Hz), 8.67 (1H, d, J=2.7 Hz), 10.38 (1H, s). Elementary analysis C6H3NOClBr, Calcd. C, 32.69; H, 1.37; N, 6.35: Found C, 32.51; H, 1.33; N, 6.18.
	With Dess-Martin periodane; In dichloromethane; at 0 - 20℃; for 12h;	To a solution of (5-bromo-2-chloropyridin-3-yl)methanol (6.8 g, 30.6 mmol) in DCM (200 mL), was added Dess-Martin periodinane (32.4 g, 76.6 mmol) at 0C. The resulting mixture was stirred at room temperature for 12h. The reaction mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (0 to 30% EtOAc in petroleum ether) to afford 5.05 g of 5-bromo-2-chloronicotinaldehyde. LCMS [M+H]+ 221.1.

	With manganese(IV) oxide; In dichloromethane; at 20℃; for 9h;Inert atmosphere;	To (5-bromo-2-choropyridin-3-y)methano (5.24 g, 22.1 mmo) in DCM (250 m) under N2 atmosphere was added Mn02 (19.2 g, 22.1 mmo). After 2h of stirring at RT, Mn02 (3.85 g, 44.2 mmo) was added, the reaction mixture was stirred for 3h at RT. Then Mn02 (1.92 g, 22.1 mmo) was added and the mixture was stirred at RT for 4h. Mn02 was coHected by fi?tration through a pad of cehte, washed with DCM and the fitrate was evaporated. The residue was purified by flash co?umn chromatography on siHca g& (hexane/TBME 1/0 to 3/7) to afford 5-bromo-2-choronicotinadehyde. Rt = 1.02 mm (UPLC Method B2), 1H NMR (400 MHz, DMSO-d5) O ppm: 10.19 (s, IH), 8.85 (d, IH), 8.39(d, IH).
		To a solution of(COC1)2 (2.95 mL, 34.84 mmol) in dried DCM (26 mL) at -78 C was added a solution of DMSO (4.94 mL, 69.7mmol) in DCM (45 mL) dropwise, and stirred at-78C for 10 mm. Then a solution of (5-bromo-2-chloropyridin-3-yl)methanol (B-2) in DCM (45 mL) was added dropwise. The mixture was stirred at -78C for 10 mm. TEA (18.2 mL, 131 mmol) was added dropwise, and stirred for 1 h at -78C. The mixture was warmed to r.t. and stirred for 1 h. The mixture was diluted with water (100 mL). Layers were separated. The organic layer was washed with water and brine, dried over MgSO4, and concentrated. The residue was purified by column chromatography on silica gel eluting with 3-5% EA in hexane to give 5-bromo-2-chloronicotinaldehyde (B-3) as a white solid. MS-ESI (m/z): 220 [M + 1]

Reference： [1]Patent: WO2009/10801,2009,A1 .Location in patent: Page/Page column 72
[2]Patent: EP1593673,2005,A1 .Location in patent: Page/Page column 98
[3]Patent: WO2011/103202,2011,A2 .Location in patent: Page/Page column 180
[4]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 76
[5]Patent: WO2017/133701,2017,A1 .Location in patent: Paragraph 157; 158

6
[ 75-16-1 ]
[ 228251-24-9 ]
[ 1111638-41-5 ]

Yield	Reaction Conditions	Operation in experiment
73.6%		Preparation of 1-(5-bromo-2-chloropyridin-3-yl)ethanol (D-2-4).To a stirred solution of compound D-2-3 (8.0 g, 36.3 mmol) in dry THF (100 mL) was added a solution of 3 M CH3MgBr in THF (18.14 mL, 54.4 mmol) dropwise at -78 0C under N2 atmosphere. After the addition, the resulting mixture was allowed to warmed up to room temperature and stirred overnight. TLC (petroleum ether/EtOAc 8:1 ) indicated most of compound D-2-3 was consumed. H2O (200 mL) was added to the reaction mixture and the mixture was extracted with EtOAc (100 mL*3). The combined organic layers were washed with saturated aqueous NaCI (200 mL), dried over Na2SO4 and concentrated in vacuo to give crude compound D-2-4, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 50:1 ) to yield pure compound D-2-4 (6.3 g, 73.6%) as a yellow oil.

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 104

7
[ 885223-63-2 ]
[ 228251-24-9 ]

Yield	Reaction Conditions	Operation in experiment
45%	With lithium aluminium tetrahydride; In tetrahydrofuran; at -10 - 20℃;	Preparation of S-bromo^-chloronicotinaldehyde (D-2-3).To a stirred solution of compound D-2-2 (25 g, 89.4 mmol) in dry THF (200 mL) was added LiAIH4 (1.7 g, 27 mmol) at -10 0C under N2 atmosphere. After the addition, the reaction mixture was allowed to warm up to room temperature and stirred overnight. TLC (petroleum ether/EtOAc 5:1 ) indicated complete consumption of starting material. To the reaction mixture was added 1 N KHSO4 (200 mL) and extracted with EtOAc (300 mL><3). The combined organic layers were washed with saturated aqueous NaCI (200 mL), dried over Na2SO4 and concentrated in vacuo to yield crude compound D-2-3, which was purified by column chromatography (silica gel, petroleum ether/EtOAc 30:1 ) to yield pure compound D-2-3 (8.0 g, 45%) as a white solid.
	With diisobutylaluminium hydride; In dichloromethane; at -78 - 0℃; for 0.5h;	To a solution of 5-bromo-2-chloro-N-methoxy-N-methylnicotinamide (E-i) (11.8 g, 42 mmol) in CDM (250 mL) was added DIBA1-H (70 mL, 105 mmol) at -78C, and the mixture was stirred at 0C for 0.5 h. The reaction solution was concentrate and the residue was purified by column chromatography on silica gel eluting with PE/EtOAc (10:1) to give 5-bromo-2-chloronicotinaldehyde (E-2). MS-ESI (m/z): 220 [M + 1].

Reference： [1]Patent: WO2009/16460,2009,A2 .Location in patent: Page/Page column 104
[2]Patent: WO2017/133701,2017,A1 .Location in patent: Paragraph 192; 193

8
1-isobutyl-2-piperidone [ No CAS ]
[ 228251-24-9 ]
[ 74-88-4 ]
[ 741702-61-4 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 1 To N-isobutyl-2-piperidone (1.13 g) was added an aqueous methanesulfonic acid solution (2.8 g/3.8 ml), and the mixture was refluxed at 120C for 2 days. The mixture was returned to room temperature, and sodium carbonate (1.55 g) was slowly added thereto. Then, the resulting solution was added dropwise to a suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.0 g) and sodium carbonate (1.25 g) in DMSO (10 ml) at 90C. After stirring as it is for 2 hours, the mixture was cooled to 0C and water was added thereto. Then, 1 N hydrochloric acid (20 ml) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue as it is was dissolved in DMF (20 ml). Then, potassium carbonate (1.25 g) and iodomethane (0.57 ml) were added thereto, and the mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. Water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and then the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1 ? hexane: ethyl acetate = 4: 1) to give methyl 5-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]pentanoate (867 mg) as a yellow oily material. 1H-NMR (300MHz, CDCl3) delta 0.82 (6H, d, J=6.6 Hz), 1.50-1.70 (4H, m), 1.92-2.05 (1H, m), 2.29 (2H, t, J=6.9 Hz), 3.28 (2H, d, J=7.5 Hz), 3.46 (2H, t, J=7.2 Hz), 3.65 (3H, s), 8.00 (1H, d, J=2.7 Hz), 8.30 (1H, d, J=2.7 Hz), 9.88 (1H, s).

Reference： [1]Patent: EP1593680,2005,A1 .Location in patent: Page/Page column 38

9
[ 2687-92-5 ]
[ 228251-24-9 ]
[ 74-88-4 ]
[ 741702-69-2 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 13 To N-isobutyl-2-pyrrolidone (1.28 g) was added an aqueous methanesulfonic acid solution (3.5 g/4.7 ml), and the mixture was refluxed at 130C for 3 days. The mixture was returned to room temperature, and sodium carbonate (1.92 g) was slowly added thereto. The resulting solution was added dropwise at 90C to a suspension of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.0 g) and sodium carbonate (1.56 g) in DMSO (13 ml), and the mixture as it is was stirred for 4 hours, followed by cooling to 0C. Water was added thereto, 6 N hydrochloric acid (5 ml) was then added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue as it is was dissolved in DMF (20 ml). Potassium carbonate (1.25 g) and iodomethane (0.57 ml) were added thereto, and the mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. Water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 12: 1 ? hexane: ethyl acetate = 4: 1) to give methyl 4-[(5-bromo-3-formylpyridin-2-yl)(isobutyl)amino]butanote (763 mg) as a yellow oily material. 1H-NMR (300MHz, CDCl3) delta 0.82 (6H, d, J=6.6 Hz), 1.88-2.04 (3H, m), 2.27 (2H, t, J=7.2 Hz), 3.28 (2H, d, J=7.5 Hz), 3.51 (2H, t, J=7.5 Hz), 3.64 (3H, s), 8.02 (1H, d, J=2.7 Hz), 8.32 (1H, d, J=2.7 Hz), 9.89 (1H, s).

Reference： [1]Patent: EP1593680,2005,A1 .Location in patent: Page/Page column 41

10
[ 15865-19-7 ]
[ 228251-24-9 ]
[ 74-88-4 ]
[ 741702-65-8 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 5 To N-propyl-2-piperidone (1.92 g) was added a 4 N aqueous sodium hydroxide solution (6.8 ml), and the mixture was refluxed at 115C for 5 hours. Thereto was added concentrated hydrochloric acid (2.27 ml) at 0C to neutralize the resulting mixture. Then, sodium carbonate (2.88 g), water (11.5 ml) and DMSO (18.2 ml) were added thereto. After the mixture was heated to 90C, a solution of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.5 g) in DMSO (23 ml) was added dropwise thereto and the mixture was stirred as it is for 2 hours. After cooling to 0C, water was added thereto. 6 N Hydrochloric acid (9 ml) was then added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue as it is was dissolved in DMF (50 ml), and then potassium carbonate (2.31 g) and iodomethane (1.04 ml) were added thereto. The mixture was stirred at room temperature under a nitrogen atmosphere for 2 hours. Water was added thereto and the mixture was then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1 ? hexane: ethyl acetate = 4: 1) to give methyl 5-[(5-bromo-3-formylpyridin-2-yl)(propyl)amino]pentanoate (909 mg) as a yellow oily material. 1H-NMR (300MHz, CDCl3) delta 0.86 (3H, t, J=7.2 Hz), 1.60-1.69 (6H, m), 2.32 (2H, t, J=6.9 Hz), 3.34-3.39 (2H, m), 3.46 (2H, t, J=6.9 Hz), 3.66 (3H, s), 8.03 (1H, d, J=2.7 Hz), 8.31 (1H, d, J=2.7 Hz), 9.88 (1H, s).

Reference： [1]Patent: EP1593680,2005,A1 .Location in patent: Page/Page column 39

11
S-4-(2-pyrrolidinyl)-3-oxabutyric acid [ No CAS ]
[ 228251-24-9 ]
[ 74-88-4 ]
[ 741269-50-1 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 47 4-(Pyrrolidin-2-yl)butanoic acid (1.39 g), <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (1.5 g) and sodium carbonate (1.88 g) were added to DMSO (30 ml) and water (15 ml), and then the mixture was stirred at 90C for 2 hours. The resulting mixture was cooled to 0C, water was added thereto, 1 N hydrochloric acid (35 ml) was then added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue as such was dissolved in DMF (50 ml), potassium carbonate (2.82 g) and iodomethane (1.27 ml) were added thereto, and then the mixture was stirred at room temperature for 2 hours under a nitrogen atmosphere. Water was added thereto, and the mixture was then extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (hexane: ethyl acetate = 10: 1 ? hexane: ethyl acetate = 4: 1) to give methyl 4-[1-(5-bromo-3-formylpyridin-2-yl)pyrrolidin-2-yl]butanoate (2.26 g) as a yellow oily material. 1H-NMR (300MHz, CDCl3) delta 1.40-2.40 (10H, m), 3.04-3.44 (1H, m), 3.66 (3H, s), 3.70-3.79 (1H, m), 4.37-4.50 (1H, m), 8.01 (1H, d, J=2.7 Hz), 8.30 (1H, d, J=2.7 Hz), 9.91 (1H, s).

Reference： [1]Patent: EP1593681,2005,A1 .Location in patent: Page/Page column 54

12
[ 741269-59-0 ]
[ 228251-24-9 ]
[ 74-88-4 ]
[ 741269-61-4 ]

Yield	Reaction Conditions	Operation in experiment
		Reference Example 55; L(-)-proline (17.0 g) was dissolved in tetrahydrofuran (350 ml) and a 1 N aqueous sodium hydroxide solution (296 ml), and then benzyl chlorocarbonate (23.2 ml) was added dropwise thereto at 0C under a nitrogen atmosphere. The resulting mixture was returned to room temperature and stirred overnight. 1 N Hydrochloric acid (296 ml) was added thereto at 0C, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give 1-[(benzyloxy)carbonyl]-L-proline, which was as such dissolved in tetrahydrofuran (250 ml), and then triethylamine (26.8 ml) was added thereto. To the resulting solution was added dropwise ethyl chlorocarbonate (16.9 ml) at 0C under a nitrogen atmosphere. The mixture was returned to room temperature and stirred for 1 hour, and the insolubles were removed by filtration. To the filtrate was added dropwise an aqueous sodium borohydride (11.2 g) solution (100 ml) at 0C, and the mixture was returned to room temperature and stirred for 3 hours under a nitrogen atmosphere. Next, water was added thereto, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with saturated brine. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane : ethyl acetate 2 : 1 ? 1 : 4) to give benzyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (25.0 g) as a colorless oily material. To a solution of oxalyl chloride (6.23 ml) in dichloromethane (70 ml) was added dropwise a solution of dimethyl sulfoxide (10.9 ml) in dichloromethane (100 ml) at -78C under an argon atmosphere. The mixture was stirred as such for 15 minutes, and then a solution of benzyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (12.0 g) in dichloromethane (80 ml) was added dropwise thereto. The mixture was stirred as such for 15 minutes, and then triethylamine (42.7 ml) was added dropwise thereto, followed by stirring as such for 20 minutes. The resulting mixture was returned to room temperature and then water was added thereto, followed by separation. The organic layer was washed with 1 N hydrochloric acid twice, an aqueous 4% sodium carbonate solution and saturated brine, respectively, and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane : ethyl acetate = 2 : 1 ? 1 : 1) to give benzyl (2S)-2-formylpyrrolidine-1-carboxylate. To [2-(1,3-dioxolan-2-yl)ethyl]triphenylphosphonium bromide (90.4 g) was added tetrahydrofuran (400 ml), further added t-butoxypotassium, and the mixture was stirred at room temperature for 1.5 hours under a nitrogen atmosphere. To the resulting mixture was added dropwise a solution of benzyl (2S)-2-formylpyrrolidine-1-carboxylate in tetrahydrofuran (200 ml), and the mixture was stirred at room temperature for 1 hour and at 50C for 3 hours under a nitrogen atmosphere. After returning to room temperature, water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane : ethyl acetate = 3 : 1 ? 2 : 1) to give benzyl (2S)-2-[3-(1,3-dioxolan-2-yl)-1-propenyl]pyrrolidine-1-carboxylate (15.1 g). Benzyl (2S)-2-[3-(1,3-dioxolan-2-yl)-1-propenyl]pyrrolidine-1-carboxylate (15.0 g) was dissolved in ethanol (200 ml), and then 10% palladium carbon (4.0 g, water content: 50%) was added thereto, followed by overnight stirring at room temperature under a hydrogen atmosphere. The insolubles were removed by filtration, and then the solvent was distilled off under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (200 ml) and a 1 N aqueous sodium hydroxide solution (150 ml), and then benzyl chlorocarbonate (10.1 ml) was added dropwise thereto at 0C under a nitrogen atmosphere. The mixture was returned to room temperature, stirred for 3 hours and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane : ethyl acetate = 7 : 1) to give benzyl (2R)-2-[3-(1,3-dioxolan-2-yl)propyl]pyrrolidine-1-carboxylate (13.6 g). Benzyl (2R)-2-[3-(1,3-dioxolan-2-yl)propyl]pyrrolidine-1-carboxylate (13.0 g) was dissolved in tetrahydrofuran (130 ml), and then 2 N hydrochloric acid (305 ml) was added thereto at 0C. After stirring the resulting mixture at room temperature for 3.5 hours, a 1 N aqueous sodium hydroxide solution (610 ml) was added thereto at 0C. The mixture was extracted with ethyl acetate, the organic layer was then washed with satura...

Reference： [1]Patent: EP1593681,2005,A1 .Location in patent: Page/Page column 56-57

13
[ 78686-79-0 ]
[ 228251-24-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 2h;	To a (-78eC) cooled and stirred solution of methyl 5-bromo-2-chloronicotinate (10.0 g, 39.9 mmol) in DCM (100 mL) was added diBAL-H (43.9 mL, 43.9 mmol, 1.6 M in hexane) dropwise and then stirred for 2h at the same temperature. Reaction was quenched with 2M aqueous HCI (50 mL) and stirred for 30 min at room temperature. Reaction mixture was filtered through the celite. The layers were separated and the aqueous layer was extracted with ethyl acetate (2/1,100 mL). The combined organic layer was washed with brine (100 mL), dried (Na2S04) and filtered. The filtrate was concentrated under vacuum and the crude product was purified by flash column chromatography (silica gel, 20-30% EtOAc in hexane system as eluent) to afford 6.50 g (74%) of the titled compound. 1HNMR (400 MHz, DMSO- d6) U10.19 (s, 1H), 8.86 (brs, 1H), 8.40 (brs, 1H); GCMS (m/z) 218.94(M)

Reference： [1]Patent: WO2018/20474,2018,A1 .Location in patent: Page/Page column 157
[2]Patent: WO2011/103202,2011,A2
[3]Patent: WO2015/181747,2015,A1

14
[ 228251-24-9 ]
[ 1332392-76-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 25℃; for 2.25h;	To a solution of step-1 intermediate (4.79 g, 21.73 mmol) in DCM (125 mL) was added catalytic amount of ethanol (0.127 mL, 2.173 mmol) followed by the addition of DAST (5.74 mL, 43.5 mmol) dropwise at 25eC for 15 min. Reaction mixture was stirred at same temperature for 2h before quenching with aqueous saturated solution of NaHCC at OeC. The layers were separated and the aqueous layer was washed with DCM. Combined organic layer was washed with brine, dried over Na2SC>4 and concentrated in vaccum and the crude product was purified by flash column chromatography (silica gel) to afford 4.60 g (87%) of the titled compound. 1HNMR (400 MHz, DMSO-d6) \|\|8.79 (d, J = 2.5 Hz, 1H), 8.42 (d, J = 2.5 Hz, 1H), 7.21 (t, J = 53.5 Hz, 1H); GCMS (m/z) 240.85 (M)+.
	With diethylamino-sulfur trifluoride;ethanol; In dichloromethane; at 20℃; for 2h;	To a solution of <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (5.05 g, 23.2 mmol) in DCM (30 niL), were added ethanol (0.13 mL, 2.32 mmol) and DAST (7.51 g, 46.4 mmol) at room temperature. The resulting mixture was stirred for 2h at that temperature. To the reaction mixture was slowly added saturated aqueous sodium bicarbonate (100 mL). The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (0 to 50% EtOAc in petroleum ether) to afford 3.80 g of 5-bromo-2-chloro-3-(difluoromethyl)pyridine. LCMS [M+H]+ 243.1.
	With diethylamino-sulfur trifluoride; In ethanol; dichloromethane; at 20℃; for 2h;Inert atmosphere;	To 5-bromo-2-choronicotinadehyde (296 g, 12.8 mmo) in DCM (75 mD under N2 atmosphere were added EtOH (0075 m, 1.27 mmo) and dropwise over 5 mm DAST (3.74 mL 25.5 mmoD at RT. The reaction mixture was stirred at RT for 2h. After coong to 0C, the reaction mixture was quenched with aqueous saturated NaHCO3, the organic phase was separated and the aqueous phase was extracted with DCM. The combined organic phases were washed with water, brine and dried over Na2SO4, fUtered and evaporated to dryness to afford 5-bromo-2-choro-3-(difluoromethy)pyridine. Rt = 1.02 mm (UPLC Method 82), H NMR (400 MHz, DM80-cl6) O ppm: 8.78 (d, IH), 8.40 (d, IH), 7.13 (t, IH), 19F NMR (400 MHz, DM80 d6) : O ppm: .117.021-116,88 (d, 2F).

Reference： [1]Patent: WO2018/20474,2018,A1 .Location in patent: Page/Page column 157
[2]Patent: WO2011/103202,2011,A2 .Location in patent: Page/Page column 181
[3]Patent: WO2015/181747,2015,A1 .Location in patent: Page/Page column 76; 77

15
[ 228251-24-9 ]
5-bromo-3-(difluoromethyl)-2-(2H-1,2,3-triazol-2-yl)pyridine [ No CAS ]

Reference： [1]Patent: WO2015/181747,2015,A1

16
[ 228251-24-9 ]
tert-butyl (5-(difluoromethyl)-6-(2H-1,2,3-triazol-2-yl)pyridin-3-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2015/181747,2015,A1
[2]Patent: WO2018/20474,2018,A1

17
[ 228251-24-9 ]
5-(difluoromethyl)-6-(2H-1.2,3-triazol-2-yl)pyridin-3-amine [ No CAS ]

Reference： [1]Patent: WO2015/181747,2015,A1
[2]Patent: WO2018/20474,2018,A1

18
[ 228251-24-9 ]
(E)-ethyl 3-(5-(benzylthio)-2-chloropyridin-3-yl)acrylate [ No CAS ]

Reference： [1]Patent: US9212182,2015,B2
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 5990 - 6017

19
[ 228251-24-9 ]
6-(benzylthio)-1-(2-chloro-3′-fluoro-5-methoxy-[1,1′-biphenyl]-4-yl)-1,8-naphthyridin-2(1H)-one [ No CAS ]

Reference： [1]Patent: US9212182,2015,B2
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 5990 - 6017

20
[ 1099-45-2 ]
[ 228251-24-9 ]
(E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran; at 20℃; for 1.5h;	A vial was charged with <strong>[228251-24-9]5-bromo-2-chloronicotinaldehyde</strong> (500 mg, 2.268 mmol, Small Molecules, Inc.) and THF (9072 mul). (Carbethoxymethylene)triphenylphosphorane (830 mg, 2.381 mmol) was added to the solution, and the mixture was stirred at RT for 1.5 h. The crude mixture was loaded onto silica gel and purified using a gradient of 0-50% EtOAc/heptane to provide (E)-ethyl 3-(5-bromo-2-chloropyridin-3-yl)acrylate (660 mg, 2.272 mmol, 100% yield) as a white solid. m/z (ESI) 291.8 (M+H)+.

Reference： [1]Patent: US9212182,2015,B2 .Location in patent: Page/Page column 557; 558
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 5990 - 6017

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• Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Julia-Kocienski Olefination • Kinetics of Alkyl Halides • Knoevenagel Condensation • Kumada Cross-Coupling Reaction • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

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Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.33
TPSA :	29.96 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.25 cm/s

Log Po/w (iLOGP) :	1.61
Log Po/w (XLOGP3) :	1.97
Log Po/w (WLOGP) :	2.31
Log Po/w (MLOGP) :	1.16
Log Po/w (SILICOS-IT) :	2.83
Consensus Log Po/w :	1.98

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

Log S (ESOL) :	-2.83
Solubility :	0.329 mg/ml ; 0.00149 mol/l
Class :	Soluble
Log S (Ali) :	-2.22
Solubility :	1.31 mg/ml ; 0.00596 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.45
Solubility :	0.0784 mg/ml ; 0.000356 mol/l
Class :	Soluble

[ CAS No. 228251-24-9 ] 5-Bromo-2-chloronicotinaldehyde

Quality Control of [ 228251-24-9 ]

Related Doc. of [ 228251-24-9 ]

Product Details of [ 228251-24-9 ]

Calculated chemistry of [ 228251-24-9 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 228251-24-9 ]

Application In Synthesis of [ 228251-24-9 ]

[ 228251-24-9 ] Synthesis Path-Downstream 1~20

Technical Information