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[ CAS No. 886365-28-2 ]

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Chemical Structure| 886365-28-2
Chemical Structure| 886365-28-2
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Product Details of [ 886365-28-2 ]

CAS No. :886365-28-2 MDL No. :MFCD07375113
Formula : C7H5BrClNO2 Boiling Point : 286.5±35.0°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :250.48 g/mol Pubchem ID :26966728
Synonyms :

Safety of [ 886365-28-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886365-28-2 ]

  • Downstream synthetic route of [ 886365-28-2 ]

[ 886365-28-2 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 886365-28-2 ]
  • [ 121359-48-6 ]
  • [ 1224846-09-6 ]
YieldReaction ConditionsOperation in experiment
bis(tri-t-butylphosphine)palladium(0); In 1,4-dioxane; at 65℃; for 3.0h;Inert atmosphere; EXAMPLE 7; Methyl 2-chloro-5-(l,3-thiazol-2-yl)isonicotinate (7-2)To a 10OmL round bottom flask was added bis(tri- tertbutylphosphine)palladium(O) (204 mg, 0.40 mmol, 0.1 equiv). The flask was then flushed with nitrogen and charged with 1,4-dioxane (20 mL), <strong>[886365-28-2]methyl 5-bromo-2-chloroisonicotinate</strong> (7^ i, 1000 mg, 4.0 mmol, 1 equiv) and 2-(tributylstannyl)-l,3-thiazole (1.5 mL, 4.8 mmol, 1.2 equiv). The reaction mixture was heated for 3 hours at 65 0C, diluted with EtOAc (20 mL) and filtered through celite. The filtrate was concentrated and the residue purified by normal phase column chromatography (0-40% EtOAc in hexanes) to afford the title compound (7-2) as a yellow solid. ESI+ MS [M+H]+ Ci0H8ClN2O2S = 255.0
  • 2
  • [ 886365-28-2 ]
  • (5-bromo-2-chloropyridin-4-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; at 0 - 25℃; for 64.0h; To a solution of methyl <strong>[886365-28-2]methyl 5-bromo-2-chloroisonicotinate</strong> (13.0 g, 51.9 mmol) in THF (100 mL) was added NaBH4 (7.85 g, 208 mmol) and LiCl (8.80 g, 208 mmol) at 0 C. The reaction was warmed to about 25 C and stirred for 64 hrs. A white suspension was formed. TLC (PE/EtOAc=l : l, by UV) showed <strong>[886365-28-2]methyl 5-bromo-2-chloroisonicotinate</strong> was consumed completely and a new spot was formed. The mixture was poured into water (300 mL) and extracted with EtOAc (200 mLx3). The combined organic layer was washed with brine (300 mLx2), dried over Na2S04 and concentrated to dryness to give (5-bromo-2-chloropyridin-4- yl)methanol (10.7 g, 92% yield) as a white solid. NMR (400 MHz, CDC13) d 2.07 (1H, brs), 4.77 (2H, d, J= 4.8 Hz), 7.60 (1H, s), 8.44 (1H, s).
79% With lithium borohydride; In tetrahydrofuran; methanol; at 0 - 20℃; for 4.0h; To a solution of <strong>[886365-28-2]methyl 5-bromo-2-chloroisonicotinate</strong> (50.2 g, 200 mmol) in tetrahydrofuran (600 mL), methanol (10.1 mL, 250 mmol) and a 4M solution of lithium borohydride in tetrahydrofuran (62.5 mL, 250 mmol) was added at 0 C. The reaction solution was stirred for 4 h at ambient temperature then quenched by slow addition of methanol (200 mL) at 0 C. The reaction mixture was diluted with ethyl acetate (200 mL), washed with brine (3 x 100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford the title compound as a colorless solid (35.2 g, 79% yield): 1H NMR (300 MHz, DMSO-i/6) delta 8.45 (s, 1H), 7.48 (s, 1H), 5.79 (t, J= 5.4 Hz, 1H), 4.47 (d, J= 4.5 Hz, 2H); MS (ES+) m/z 222.1, 224.2 (M + 1).
  • 3
  • [ 886365-28-2 ]
  • 5-bromo-2-chloro-4-((3,4-dichlorophenoxy)methyl)pyridine [ No CAS ]
  • 4
  • [ 886365-28-2 ]
  • 5-bromo-4-((3,4-dichlorophenoxy)methyl)-2-hydrazinylpyridine [ No CAS ]
  • 5
  • [ 886365-28-2 ]
  • N-(6-bromo-7-((3,4-dichlorophenoxy)methyl)-[1,2,4]-triazolo[4,3-a]pyridin-3-yl)methanesulfonamide [ No CAS ]
  • 6
  • [ 886365-28-2 ]
  • 6-bromo-7-[(3,4-dichlorophenoxy)methyl]-[1,2,4]triazolo[4,3-a]pyridin-3-amine [ No CAS ]
  • 7
  • [ 67-56-1 ]
  • 5-bromo-2-chloropyridine-4-carboxylic acid [ No CAS ]
  • [ 886365-28-2 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; at 75℃; for 8.0h; 5-bromo-2-chloroisonicotinic acid (30.0 g, 12.6 mmol) was dissolved in methanol (300 mL), then SOCl2 (18.0 g, 15 mmol) was added, the mixture was heated to 75 C. for 8 h. The reaction was completed monitored by LCMS. The mixture was cooled to room temperature and concentrated by reduced pressure, and then EtOAc (300 mL) was added to the residue. The mixture was washed with a saturated aqueous solution of NaHCO3, dried over anhydrous Na2SO4, filtered and concentrated to obtain methyl 5-bromo-2-chloroisonicotinate (32.0 g, yield: 99%). MS (ESI): m/z 251.9 [M+1]+.
95% With thionyl chloride; at 0 - 20℃; for 4.0h; To a solution of 5-bromo-2-chloroisonicotinic acid (50.0 g, 211 mmol) in methanol (200 mL) was added thionyl chloride (50 mL) at 0 C. The reaction was warmed to ambient temperature and then refluxed for 4 h. After cooling to ambient temperature, the solvent was concentrated in vacuo. The residue was diluted with diethyl ether (100 mL), washed with saturated aqueous sodium hydrogencarbonate (3 x 50 mL), brine (3 x 50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was in vacuo to afford the title compound as a pale yellow liquid (50.2 g, 95% yield): 1H NMR (300 MHz, DMSO-
94% With thionyl chloride; at 0 - 70℃; for 3.0h; To a suspension of 5-bromo-2-chloroisonicotinic acid (5.00 g, 21.2 mmol) in MeOH (50 mL) was added dropwise SOCh (8.20 g, 69.0 mmol, 5 mL) at 0 C. The reaction was warmed to about 20 C and then refluxed (70 C) for 3 hrs. A slight yellow cloudy was formed. TLC (PE/EtOAc=l : l, by UV) showed 5-bromo-2-chloroisonicotinic acid (Rf~0) was consumed completely and a new spot (Rf~0.5) was formed. After cooling to 20 C, the solvent was concentrated in vacuum. The residue was diluted with EtOAc (200 mL), washed with saturated aqueous NaHCCh (100 mL x2), brine (100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuum to afford methyl 5-bromo-2- chloroisonicotinate (5.00 g, yield: 94%) as yellow liquid. (1069) NMR (400 MHz, DMSO-rie) d 3.92 (s, 3H), 7.90 (s, 1H), 8.79 (s, 1H).
To a solution of 5-bromo-2-chloroisonicotinic acid (Combi-Blocks, 100 g, 423 mmol) in THF (200 mL) and toluene (800 mL) was added DMF (1.6 mL, 21.15 mmol) . To the resulting slurry was added slowly oxalyl chloride (47 mL, 529 mmol) . The reaction was stirred over the weekend at room temperature. Then MeOH (100 mL) was added slowly while cooling in awater bath. After 2 h at room temperature, aqueous K2HPO4 (1 M, 423 mL, 423 mmol) was added slowly while cooling in a water bath. The layers were separated and the aqueous layer was extracted with toluene (1 x 250 mL) . The combined organic layers were filtered through Solca-FlocTM cellulose, then washed with water (1 x 200 mL) , dried over MgSO4 and concentrated in vacuo to give the crude methyl ester intermediate. To the methyl ester intermediate in toluene (2 L) was added chloro [tris (2-methylphenyl) phosphine] [2- (2'-amino-1, 1'-biphenyl) ] palladium (II) (2.6 g, 4.23 mmol, 1) and N, N-dicyclohexylmethylamine (226 mL, 1057 mmol) . The reaction was degassed for 1 h, then t-butyl acrylate was added in a single portion and the reaction mixture was heated to 80overnight. Then additional chloro [tris (2-methylphenyl) phosphine] [2- (2'-amino-1, 1'-biphenyl) ] palladium (II) (1.3 g, 2.12 mmol, 0.5) was added and the reaction was heated at 80for 3 h. The reaction mixture was then cooled to room temperature and quenched with water (500 mL) . The organic layer was separated, washed with saturated brine (1 x 500 ml) , then filtered through a plug of silica gel (150 g) and rinsed with 20EtOAc in hexanes. The filtrate was concentrated in vacuo to give a crude oil, which was recrystallized from EtOAc in hexane (1:1) at -10to provide the title compound. MS (ESI) m/e (M+H+) : 242.2.
To a solution of 5-bromo-2-chloroisonicotinic acid (Combi-Blocks, 100 g, 423 mmol) in THF (200 mL) and toluene (800 mL) was added DMF (1.6 mL, 21.15 mmol). To the resulting slurrywas added slowly oxalyl chloride (47 mL, 529 mmol). The reaction was stirred over the weekend at room temperature. Then MeOH (100 mL) was added slowly while cooling in a water bath. After 2 h at room temperature, aqueous K2HPO4 (1 M, 423 mL, 423 mmol) was added slowly while cooling in a water bath. The layers were separated and the aqueous layer was extracted with toluene (1 x 250 mL). The combined organic layers were filtered throughSolka-F1ocTM cellulose, then washed with water (1 x 200 mL), dried over Mg504 and concentrated in vacuo to give the crude methyl ester intermediate. To the methyl ester intermediate in toluene (2 L) was added chloro[tris(2-methylphenyl)phosphine] [2-(2?-amino- i,i?-biphenyl)]palladium(II) (2.6 g, 4.23 mmol, 1%) and N,N-dicyclohexylmethylamine (226mL, 1057 mmol). The reaction was degassed for 1 h, then t-butyl acrylate was added in a single portion and the reaction mixture was heated to 80 C overnight. Then additional chloro[tris(2- methylphenyl)phosphine] [2-(2?-amino- 1,1 ?-biphenyl)]palladium(II) (1.3 g, 2.12 mmol, 0.5%) was added and the reaction was heated at 80 C for 3 h. The reaction mixture was then cooled toroom temperature and quenched with water (500 mL). The organic layer was separated, washed with saturated brine (1 x 500 ml), then filtered through a plug of silica gel (150 g) and rinsed with 20% EtOAc in hexanes. The filtrate was concentrated in vacuo to give a crude oil, which was recrystallized from EtOAc in hexane (1:1) at -10 C to provide the title compound. MS (ESI) mle (M+H): 242.2.
To a solution of 5-bromo-2-chloroisonicotinic acid i-i la (Combi-Blocks, 100 g, 423 mmol) in THF (200 mL) and toluene (800 mL) was added DIVIF (1.6 mL, 21.15 mmol). To the resulting slurry was added slowly oxalyl chloride (47 mL, 529 mmol). The reaction was stirred over the weekend at room temperature. Then MeOH (100 mL) was added slowly while cooling in a water bath. After 2h at room temperature, aqueous K2HPO4 (1 M, 423 mL, 423 mmol) was added slowly while still cooling in a water bath. The layers were separated and the aqueous layer was extracted with toluene (1 x 250 mL). The combined organic layers were filtered through Solka-Floc cellulose, then washed with water (1 x 200 mL), dried over Mg504 and concentrated in vacuo to give the crude methyl ester intermediate. To the methyl ester intermediate in toluene (2 L) was added chloro[tris(2-methylphenyl)phosphine] [2-(2?-amino-i,i?-biphenyl)]palladium(II) (2.6 g, 4.23 mmol, 1%) and N,N-dicyclohexylmethylamine (226 mL, 1057 mmol). The reaction was degassed for 1 h, then tButyl acrylate was added in a single portion and the reaction mixture was heated to 80C overnight. Then additional chloro[tris(2-methylphenyl)phosphine] [2-(2?-amino- 1,1 ?-biphenyl)]palladium(II) (1.3 g, 2.12 mmol, 0.5%) was added and the reaction was heated at 80C for 3 h. The reactionmixture was then cooled to room temperature and quenched with water (500 ml). The layers were separated. The organic layer was washed with saturated brine (1 x 500 ml), then filtered through a plug of silica gel (150 g) and rinsed with 20% EtOAc in hexanes. The filtrate was concentrated in vacuo to give a crude oil, which was recrystallized from EtOAc in hexane (1:1) at -10C to provide compound 1-lib. MS (ESI) m/e (M+H): 242.2.
With thionyl chloride; at 0 - 80℃; for 10.0h; To a solution of 5-bromo-2-chloroisonicotinic acid (30 g, 127 mmol) in MeOH (300 mL) was added SOd2 (27.8 mL, 381 mmol) at 0 C. The solution was then heated to and stirred at 80 C for 10 h. The resulting mixture was concentrated in vacuum and the residue was purified by flash silica gel chromatography (eluting with ethyl acetate/pet. ether gradient) to give methyl5-bromo-2-chloroisonicotinate as colorless oil. MS: 250/252 (M + 1/M + 3). ?H NIVIR (400 IVIFIz,CDC13) 8.58 (s, 1H), 7.63 (s, 1H), 3.94 (s, 3H).

  • 8
  • [ 886365-28-2 ]
  • (E)-5-(3-(tert-butoxy)-3-oxoprop-1-en-1-yl)-2-chloroisonicotinic acid [ No CAS ]
  • 9
  • [ 886365-28-2 ]
  • (E)-tert-butyl 3-(6-chloro-4-((E)-2-chloro-2-hydrazonoacetyl)pyridin-3-yl)acrylate [ No CAS ]
  • 10
  • [ 886365-28-2 ]
  • (E)-tert-butyl 3-(6-chloro-4-(2-diazoacetyl)pyridin-3-yl)acrylate [ No CAS ]
  • 11
  • [ 886365-28-2 ]
  • (5aR,6R,6aS)-tert-butyl 3-chloro-5-oxo-5,5a,6,6a-tetrahydrocyclopropa-[4.5]cyclopenta-[1,2-c]pyridine-6-carboxylate [ No CAS ]
  • 12
  • [ 886365-28-2 ]
  • C14H16ClNO3 [ No CAS ]
  • 13
  • [ 886365-28-2 ]
  • (5aR,6S,6aS)-tert-butyl 3-chloro-5,5a,6,6a-tetrahydrocyclo-propa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate [ No CAS ]
  • 14
  • [ 886365-28-2 ]
  • (5aR,6S,6aS)-tert-butyl 3-(2-(trimethylsilyl)ethoxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate [ No CAS ]
  • 15
  • [ 886365-28-2 ]
  • (5aR,6S,6aS)-tert-butyl 3-hydroxy-5,5a,6,6a-tetrahydrocyclopropa[4,5]-cyclopenta[1,2-c]pyridine-6-carboxylate [ No CAS ]
  • 16
  • [ 886365-28-2 ]
  • (5aR,6S,6aS)-tert-butyl 3-((5-bromo-2,4-difluorobenzyl)oxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate [ No CAS ]
  • 17
  • [ 886365-28-2 ]
  • (5aR,6S,6aS)-tert-butyl 3-((2,4-difluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)-5,5a,6,6a-tetrahydrocyclopropa[4,5]cyclopenta[1,2-c]pyridine-6-carboxylate [ No CAS ]
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