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[ CAS No. 89466-16-0 ]

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Chemical Structure| 89466-16-0
Chemical Structure| 89466-16-0
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Product Details of [ 89466-16-0 ]

CAS No. :89466-16-0 MDL No. :MFCD17014961
Formula : C6H7BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :187.04 g/mol Pubchem ID :59605384
Synonyms :

Safety of [ 89466-16-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89466-16-0 ]

  • Downstream synthetic route of [ 89466-16-0 ]

[ 89466-16-0 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 13922-41-3 ]
  • [ 89466-16-0 ]
  • 3-methyl-6-(naphthalen-1-ylmethyl)pyridin-2-amine [ No CAS ]
  • 2
  • [ 1306734-44-0 ]
  • [ 89466-16-0 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-5-methyl-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In toluene; at 60℃; for 20h; (1R,3S,5R)-2-(tert-butoxycarbonyl)-5-methyl-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (1 equiv), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (1.2 equiv), EEDQ (1.2 equiv) in toluene (10 vol) was stirred for 20h at 60 °C. The solvent was removed under reduced pressure and the remaining residue was dissolved in DCM ,Washed with IN HCl and washed with aq NaHCCb and dried over Na2S04. The solvent was removed and the residue was added to DCM/heptane (1 :3, 8 vol ) and stirred 10 min at RT and cooled to 5 °C. The precipitated solid was then filtered and directly used in the next reaction.
  • 3
  • [ 89466-16-0 ]
  • (2S,4R)-N-(6-bromo-3-methylpyridin-2-yl)-4-fluoropyrrolidine-2-carboxamide hydrochloride [ No CAS ]
  • 4
  • [ 89466-16-0 ]
  • (2S,4R)-1-(2-(3-acetyl-5-((5-methyipyrimidin-2-yl)oxy)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-4-fluoropyrrolidine-2-carboxamide [ No CAS ]
  • 5
  • [ 89466-16-0 ]
  • (2S,4R)-1-(2-(3-acetyl-5-((5-methylpyrazin-2-yl)oxy)-1H-indazol-1-yl)acetyl)-N-(6-bromo-3-methylpyridin-2-yl)-4-fluoropyrrolidine-2-carboxamide [ No CAS ]
  • 6
  • [ 89466-16-0 ]
  • [ 203866-14-2 ]
  • tert-butyl (2S,4R)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% To a stirred solution of (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-50° C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-50° C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-5° C. Then <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (200 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and 430 mg (quantitative yield) of titled compound was obtained.
Step 1: terf-Butyl (2S,4R)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyI)-4- fluoropyrrolidine-l-carboxylate (209) [0696] To an ice cold solution of (2S,4R)-l -(feri-butoxycarbonyl)-4-fluoropyrrolidine-2- carbox lic acid (1 equiv) in DCM (10 vol) was added l-chloro-N,N,2-trimethyl-l-propenylamine ( 1 , 1 equiv) dropwise with stirring. Stirring was continued for 3 h at this temperature, and then 6- bromo-3-methylpyridin-2-amine (1.1 equiv) was added, followed by DIEA (3 equiv). The cooling bath was removed and the reaction mixture was stirred overnight at rt. The reaction mixture was then added to water and extracted with DCM. The organic layer was washed successively with an aqueous solution of NaHCCb, water and brine, then dried over Na2SO<i and concentrated under reduced pressure. The remaining residue was purified by column chromatography on silica gel (DCM EtOAc) to give compound 209.
  • 7
  • [ 334769-80-1 ]
  • [ 89466-16-0 ]
  • tert-butyl (2S,5S)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-5-methylpyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
310 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; In a pre-dried flask, (2S,5 S)? 1-(tert-butoxycarbonyl)-5-methylpyrrolidine-2-carboxylic acid (purchased from Aldrich) (230 mg, 1.0 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (188 mg, 1.0 mmol) are placed, and then anhydrous DCM (15 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (0.25 mL, 3.0 mmol) was added in one portion, followed by addition of POCl3(100 muL, 1.0 mmol). After completion of addition, the mixture was stirred for 4 hours at 0° C., and then the reaction was quenched with water (15 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (15 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was purified to give 310.0 mg pure product.1H NMR (400 MHz, DMSO-d6): (major rotamer) delta 1.21 (d, J=6.4 Hz, 3H), 1.37 (s, 9H), 1.97-2.00 (m, 2H), 1.57 (s, 1H), 2.11 (s, 3H), 2.15-2.22 (m, 1H), 3.88 (s, 1H), 4.35 (t, J=8.0 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 10.23 ppm. LC (method A): tR=2.11 min. LC/MS (EI) m/z: [M+H]398.25
  • 8
  • [ 364750-81-2 ]
  • [ 89466-16-0 ]
  • tert-butyl (2S,4S)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-4-methylpyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
194 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; In a pre-dried flask, (2 S,4 S)-1-(tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid (purchased from Aldrich) (230 mg, 1.0 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (188 mg, 1.0 mmol) are placed, and then anhydrous DCM (15 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (0.25 mL, 3.0 mmol) was added in one portion, followed by addition of POCl3(100 muL, 1.0 mmol). After completion of addition, the mixture was stirred for 4 hours at 0° C., and then the reaction was quenched with water (15 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (15 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was purified to give 194 mg pure product.1H NMR (400 MHz, DMSO-d6): (major rotamer) delta 1.06 (d, J=6.4 Hz, 3H), 1.35 (s, 9H), 1.38-1.49 (m, 1H), 2.11 (s, 3H), 2.15-2.25 (m, 1H), 2.42-2.50 (m, 1H), 2.84-2.90 (m, 1H), 3.61-3.65 (m, 1H), 4.28 (t, J=8.0 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 10.25 ppm. LC (method A): tR=2.00 min. LC/MS (EI) m/z: [M+H]398.25
  • 9
  • [ 89466-16-0 ]
  • [ 364750-80-1 ]
  • tert-butyl (2S,4R)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-4-methylpyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
227 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; In a pre-dried flask, (2S,4R)-1-(tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid (purchased from Synthonix) (230 mg, 1.0 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (188 mg, 1.0 mmol) are placed, and then anhydrous DCM (15 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (0.25 mL, 3.0 mmol) was added in one portion, followed by addition of POCl3(100 muL, 1.0 mmol). After completion of addition, the mixture was stirred for 4 hours at 0 C., and then the reaction was quenched with water (15 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (15 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was purified to give 227 mg of pure product.1HNMR (400 MHz, DMSO-d6): (major rotamer) delta 0.99 (d, J=6.4 Hz, 3H), 1.36 (s, 9H), 1.82-1.93 (m, 1H), 2.02-2.06 (m, 1H), 2.11 (s, 3H), 2.30-2.37 (m, 1H), 2.86 (t, J=8.0 Hz, 1H), 3.57-3.61 (m, 1H), 4.35 (t, J=8.0 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 10.25 ppm. LC (method A): tR=2.04 min. LC/MS (EI) m/z: [M+H]398.25
  • 10
  • [ 89466-16-0 ]
  • [ 197142-36-2 ]
  • tert-butyl (1S,3S,5S)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
302 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; In a pre-dried flask, (1S,3S,5S)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (228 mg, 1.0 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (188 mg, 1.0 mmol) are placed, and then anhydrous DCM (15 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (0.25 mL, 3.0 mmol) was added in one portion, followed by addition of POCl3(100 muL, 1.0 mmol). After completion of addition, the mixture was stirred for 4 hours at 0° C., and then the reaction was quenched with water (15 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (15 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was purified to give 302.0 mg pure product.1H NMR (400 MHz, DMSO-d6): (major rotamer) delta 0.62-0.64 (m, 1H), 0.97 (s, br, 1H), 1.34 (s, 9H), 1.49-1.58 (m, 1H), 1.90-1.96 (m, 1H), 2.10 (s, 3H), 2.54-2.69 (m, 1H), 3.37-3.41 (m, 1H), 4.66 (t, J=11.2 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.63 (t, J=7.6 Hz, 1H), 10.31 ppm. LC (method A): tR=2.01 min. LC/MS (EI) m/z: [M+H]396.15, 398.25
  • 11
  • [ 89466-16-0 ]
  • [ 160033-52-3 ]
  • tert-butyl (2S,5R)-2-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-5-methylpyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
188 mg With pyridine; trichlorophosphate; In dichloromethane; at 0℃; for 4h; In a pre-dried flask, (2S,5 S)? 1-(tert-butoxycarbonyl)-4-methylpyrrolidine-2-carboxylic acid (230 mg, 1.0 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (188 mg, 1.0 mmol) are placed, and then anhydrous DCM (15 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (0.25 mL, 3.0 mmol) was added in one portion, followed by addition of POCl3(100 muL, 1.0 mmol). After completion of addition, the mixture was stirred for 4 hours at 0° C., and then the reaction was quenched with water (15 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (15 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was purified to give 188 mg pure product.1H NMR (400 MHz, DMSO-d6): (major rotamer) delta 1.12 (t, J=8.8 Hz, 3H), 1.34 (s, 9H), 1.46-1.55 (m, 1H), 1.84-1.91 (m, 1H), 2.02-2.08 (m, 1H), 2.11 (s, 3H), 2.28-2.37 (m, 1H), 3.95-4.02 (m, 1H), 4.35 (t, J=8.8 Hz, 1H), 7.43 (d, J=7.6 Hz, 1H), 7.62 (t, J=7.6 Hz, 1H), 10.26 ppm. LC (method A): tR=2.10 min. LC/MS (EI) m/z: [M+H]398.25
  • 12
  • [ 400720-05-0 ]
  • [ 89466-16-0 ]
  • tert-butyl (1S,2S,5R)-2-((6-bromopyridin-2-yl)carbamoyl)-3-azabicyclo[3.1.0]hexane-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To an ice cold solution of (1S,2S,5R)-3-(tert-butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (103 mg, 0.45 mmole) in 6 mL of CH2Cl2, 1-chloro-N,N,2-trimethylprop-1-en-1-amine (0.07 mL, 1.1 equiv) was added drop-wise with stirring. The stirring was continued for 3 hours at the same temperature. Then <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (93 mg, 1.0 equiv) was added, followed by 0.23 mL (3 equiv) Hunig's base. The cooling bath was removed and the reaction mixture was stirred at room temperature for overnight. The solvent was co-evaporated with 5 mL of MeOH, and the residue was purified by ISCO (eluted 5percent MeOH in DCM, gradient) to obtain 160 mg (90percent) of title compound as yellow oil.
  • 13
  • [ 89466-16-0 ]
  • (1R,3S,4S)-2-aza-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid 2-tert-butyl ester [ No CAS ]
  • tert-butyl (3S,4S)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; trichlorophosphate; In dichloromethane; at 20℃;Cooling with ice; In a pre-dried flask, (3S,4S)-2-(tert-butoxycarbonyl)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid (48 mg, 0.2 mmol), <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (37 mg, 0.2 mmol) are placed, and then anhydrous DCM (5 mL) was added. The flask was placed in an ice bath. To the solution, dry pyridine (50 muL, 0.6 mmol) was added in one portion, followed by addition of POCl3(20 muL, 0.2 mmol). After completion of addition, the mixture was stirred overnight at room temperature, and then the reaction was quenched with water (5 mL). The DCM layer was collected and the aqueous phase was extracted with DCM (10 mL×2). The combined DCM solution was washed with brine, and dried over MgSO4. The solution was filtered and concentrated; the resulting residue was used for next step without further purification.
  • 14
  • (3S)-2-(tert-butoxycarbonyl)-5-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid [ No CAS ]
  • [ 89466-16-0 ]
  • (3S)-tert-butyl 3-(6-bromo-3-methylpyridin-2-ylcarbamoyl)-5-(hydroxymethyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 90℃; To a solution of scheme 8-38 compound S1 (1 g, 3.89 mmol) and <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (870 mg, 4.67 mmol) in DCE (10 ml) was added DIPEA (2.56 mL, 15.56 mmol) and EEDQ (1.92 g, 7.78 mmol). The reaction was stirred at 90 C. overnight. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate=2:1) to afford compound 2 (710 mg, 43.0% yield) as a white solid. LC/MS (ESI) m/z: 426 (M+H)+.
43.0% With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 90℃; To a solution of scheme 8-38 compound S1 (1 g, 3.89 mmol) and <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (870 mg, 4.67 mmol) in DCE (10 ml) was added DIPEA (2.56 mL, 15.56 mmol) and EEDQ (1.92 g, 7.78 mmol). The reaction was stirred at 90 oC overnight. The solvent was removed under vacuum. The residue was purified by column chromatography on silica gel (petroleum ether: ethyl acetate =2: 1) to afford scheme 8-38 compound S2 (710 mg, 43.0% yield) as a white solid. LC/MS (ESI) m/z: 426 (M+H)+.
  • 15
  • [ 89466-16-0 ]
  • [ 197142-34-0 ]
  • tert-butyl (1R,3S,5R)-3-((6-bromo-3-methylpyridin-2-yl)carbamoyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a stirred solution of (1R,3S,5R)-2-(tert-butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid (261 mg, 1.16 mmole) in 15 mL of CH2Cl2, was added 1-methyl imidazole (0.23 mL, 2.5 equiv.) at 0-5° C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5° C. and then added methane sulfonyl chloride (0.11 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50° C. Then <strong>[89466-16-0]6-bromo-3-methylpyridin-2-amine</strong> (217 mg, 1 equiv) was added, and stirred for 18h at room temperature. Water (10 mL) was added to the reaction mixture, layers were separated and aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was washed with 1N HCl (10 mL), followed by Sat NaHCO3 (10 mL) and then with brine (10 mL). Combined organic layer was dried over Na2SO4, concentrated and 371 mg (94percent yield) of titled compound was obtained.
  • 16
  • (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoro-4-(fluoromethyl)pyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 89466-16-0 ]
  • C17H22BrF2N3O3 [ No CAS ]
  • 17
  • (2S,4R)-1-(tert-butoxycarbonyl)-4-fluoro-4-(fluoromethyl)pyrrolidine-2-carboxylic acid [ No CAS ]
  • [ 89466-16-0 ]
  • (x)C2HF3O2*C12H14BrF2N3O [ No CAS ]
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