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Chemical Structure| 1022641-52-6 Chemical Structure| 1022641-52-6

Structure of 1022641-52-6

Chemical Structure| 1022641-52-6

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Product Details of [ 1022641-52-6 ]

CAS No. :1022641-52-6
Formula : C6H7BrN2
M.W : 187.04
SMILES Code : CNC1=CC=C(N=C1)Br
MDL No. :MFCD00234191
InChI Key :OAXOGPDQYIWCST-UHFFFAOYSA-N
Pubchem ID :817178

Safety of [ 1022641-52-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H315-H318-H335
Precautionary Statements:P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P330-P332+P313-P362-P403+P233-P405-P501
Class:8
UN#:3259
Packing Group:

Application In Synthesis of [ 1022641-52-6 ]

* 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 [ 1022641-52-6 ]

[ 1022641-52-6 ] Synthesis Path-Downstream   1~10

YieldReaction ConditionsOperation in experiment
General procedure: A solution of 3-amino-6-chloropyridine (2.46 g, 19.2 mmol) in THF (50 mL) was added to a suspension of NaH (60% dispersion in mineral oil, 768 mg, 19.2 mmol) and THF (150 mL). The reaction stirred at room temperature for 3 hours, lodomethane (1.2 mL, 19.2 mmol) was added and the reaction was heated to 40 C for 9 hours. After cooling to room temperature, the solvent was removed. The crude material was tritrated in dichloromethane (100 mL) and filtered to remove any salts. The filtrate was purified by flash chromatography (silica, 10-80% ethyl acetate/hexanes). 1H NMR (400 MHz, CDCI3) 5 7.72 (d, J= 3.1, 1H), 7.06 (d, J= 8.6, 1H), 6.83 (dd,J= 3.1, 8.6, 1H), 3.78 (s, 1H), 2.84 (d, J= 19.7, 3H).
  • 2
  • tert-butyl (6-bromopyridin-3-yl)(methyl)carbamate [ No CAS ]
  • [ 1022641-52-6 ]
YieldReaction ConditionsOperation in experiment
66% With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 3h; To a stirred solution of the compound obtained in the previous section, step a, (1.3 g, 4.54 mmol) in DCM (5ml) was added TFA (3 ml) at ooc and allowed to stir at RT for 3 h. The reaction mixture was concentrated andthe residue was washed with n-pentane and diethyl ether. The obtained compound was dissolved in water andbasified to pH-8 using saturated NaHC03 solution and the precipitated solid was filtered, washed with water15 and dried to afford the title compound (0.9 g, 66%) as a free base.LC-MS (method 1 ): R1 = 1.47 min; m/z = 186.91 (M+H+).
66% With trifluoroacetic acid; In dichloromethane; at 0 - 20℃; for 3h; To a stirred solution of the compound obtained in the previous section, step a, (1.3 g, 4.54 mmol) in DCM (5 mL) was added TFA (3 mL) at 0C and allowed to stir at RT for 3 h. The reaction mixture was concentrated and the residue was washed with n-pentane and diethyl ether. The obtained compound was dissolved in water and basified to pH-8 using saturated NaHCCb solution and the precipitated solid was filtered, washed with water and dried to afford the title compound (0.9 g, 66%) as a free base. (0650) LC-MS (method 1): R, = 1.47 min; m/z = 186.91 (M+H+).
  • 3
  • [ 3303-84-2 ]
  • [ 1022641-52-6 ]
  • tert-butyl (3-((6-bromopyridin-3-yl)(methyl)amino)-3-oxopropyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 16h; To a stirred solution of the compound obtained in the previous section, step b, (450 mg, 2.41 mmol) and 3-(tertbutoxycarbonylamino)propanoic acid (457 mg, 2.41 mmol) in DCM (10 ml) was added EhN (1.7 ml, 12.0920 mmol) and T3P (2.3 g, 7.25 mmol) at RT. The reaction mixture was stirred at RT for 16h. The reaction mixturewas diluted with DCM (20 ml) and water (20 ml). Separated the organic layer, washed with water (20 ml),brine solution (10 ml) and dried over anhydrous Na2S04 and concentrated. The crude compound was purifiedby flash column chromatography and eluted at 50% EtOAc/Pet Ether to afford the title compound (0.3 g, 35%)as a white solid.25 LC-MS (method 1 ): Rt = 1.86 min; m/z = 358.20 (M+H+).
35% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In dichloromethane; at 20℃; for 16h; To a stirred solution of the compound obtained in the previous section, step b, (450 mg, 2.41 mmol) and 3-(tert- butoxycarbonylamino) propanoic acid (457 mg, 2.41 mmol) in DCM (10 mL) was added EN (1.7 mL, 12.09 mmol) and T3P (2.3 g, 7.25 mmol) at RT. The reaction mixture was stirred at RT for 16h. The reaction mixture was diluted with DCM (20 mL) and water (20 mL). Separated the organic layer, washed with water (20 mL), brine solution (10 mL) and dried over anhydrous NajSC and concentrated. The crude compound was purified by flash column chromatography and eluted at 50% EtOAc/Pet Ether to afford the title compound (0.3 g, 35%) as a white solid. (0653) LC-MS (method 1); Rt = 1.86 min; m/z = 358.20 (M+H~).
  • 4
  • [ 218594-15-1 ]
  • [ 1022641-52-6 ]
  • 5
  • [ 13534-97-9 ]
  • [ 1022641-52-6 ]
  • 6
  • [ 1022641-52-6 ]
  • [ 7051-34-5 ]
  • 6-bromo-N-(cyclopropylmethyl)-N-methylpyridin-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.2% To a stirred solution of 6-bromo-W-methylpyridin-3-amine (1200 mg, 6.44mmol) in DMF, 60% NaH (1030 mg, 25.76mmol) was added at 0C and stirred at rt for 15 minutes. It was cooled at 0C, and (bromomethyl)cyclopropane (1738 mg, 12.88 mmol) was added. It was allowed to stir at rt for 1 h. The reaction mixture was cooled to 0C, quenched with water and extracted with EtOAc. The separated organic layer was washed with water and brine solution and dried over anhydrous Na2S04, filtered and concentrated under reduced pressure. The crude compound was purified by column chromatography and eluted at 15% EtOAc in pet ether to afford the title compound (1.0 g, 64.2 %) as a yellow gummy;LC-MS (method 5): Rt = 1.20 min; m/z = 240.97 (M+H+).
  • 7
  • [ 24424-99-5 ]
  • [ 1022641-52-6 ]
  • tert-butyl (6-bromopyridin-3-yl)(methyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.42% With dmap; In tetrahydrofuran; at 80℃; for 48h; Step 1. Synthesis of tert-butyl N-(6-bromo-3-pyridyl)-N-methyl-carbamate [0932] 6-bromo-N-methyl-pyridin-3-amine (8 g, 42.77 mmol) and DMAP (104.51 mg, 855.45 μmol) were dissolved in THF (40 mL) and Di-tert-butyl dicarbonate (28.00 g, 128.32 mmol, 29.45 mL) was added dropwise. The reaction mixture was stirred for 48 hr at 80 C . The resulting mixture was evaporated in vacuo, poured into aqeous NaHCO3(conc.) solution (50 ml) and and extracted with EtOAc (2x30 ml). The combined organic extracts were washed with water(2*40 ml), dried over sodium sulphate and evaporated in vacuo to afford tert-butyl N-(6- bromo-3-pyridyl)-N-methyl-carbamate (10 g, 34.82 mmol, 81.42% yield) 1H NMR (500 MHz, CDCl3) δ (ppm) 1.46 (s, 9H), 3.27 (s, 3H), 7.25 (s, 1H), 7.41 (d, 1H), 7.49 (m, 1H), 8.29 (s, 1H). LCMS(ESI): [M-Boc]+ m/z: calcd 287.2; found 289.0; Rt = 1.276 min
81.42% With dmap; In tetrahydrofuran; at 80℃; for 48h; Step 1. Synthesis of tert-butyl N-(6-bromo-3-pyridyl)-N-methyl-carbamate [0932] 6-bromo-N-methyl-pyridin-3-amine (8 g, 42.77 mmol) and DMAP (104.51 mg, 855.45 μmol) were dissolved in THF (40 mL) and Di-tert-butyl dicarbonate (28.00 g, 128.32 mmol, 29.45 mL) was added dropwise. The reaction mixture was stirred for 48 hr at 80 C . The resulting mixture was evaporated in vacuo, poured into aqeous NaHCO3(conc.) solution (50 ml) and and extracted with EtOAc (2x30 ml). The combined organic extracts were washed with water(2*40 ml), dried over sodium sulphate and evaporated in vacuo to afford tert-butyl N-(6- bromo-3-pyridyl)-N-methyl-carbamate (10 g, 34.82 mmol, 81.42% yield) 1H NMR (500 MHz, CDCl3) δ (ppm) 1.46 (s, 9H), 3.27 (s, 3H), 7.25 (s, 1H), 7.41 (d, 1H), 7.49 (m, 1H), 8.29 (s, 1H). LCMS(ESI): [M-Boc]+ m/z: calcd 287.2; found 289.0; Rt = 1.276 min
  • 8
  • [ 1022641-52-6 ]
  • tert-butyl 6-[5-[tert-butoxycarbonyl(methyl)amino]-2-pyridyl]-3-methyl-3,4-dihydro-2H-pyridine-1-carboxylate [ No CAS ]
  • 9
  • [ 1022641-52-6 ]
  • N-methyl-6-(3-methyl-2,3,4,5-tetrahydropyridin-6-yl)pyridin-3-amine [ No CAS ]
  • 10
  • [ 1022641-52-6 ]
  • N-methyl-6-(5-methyl-2-piperidyl)pyridin-3-amine [ No CAS ]
 

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Technical Information

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[ 1022641-52-6 ]

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