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[ CAS No. 13473-01-3 ] {[proInfo.proName]}

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Chemical Structure| 13473-01-3
Chemical Structure| 13473-01-3
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Product Details of [ 13473-01-3 ]

CAS No. :13473-01-3 MDL No. :MFCD06254388
Formula : C6H6ClNO Boiling Point : -
Linear Structure Formula :- InChI Key :NPYYXUYLIHZYOU-UHFFFAOYSA-N
M.W : 143.57 Pubchem ID :4738276
Synonyms :

Safety of [ 13473-01-3 ]

Signal Word:Danger Class:3,8
Precautionary Statements:P280-P305+P351+P338 UN#:2924
Hazard Statements:H225-H302-H318 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 13473-01-3 ]

* 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 [ 13473-01-3 ]

[ 13473-01-3 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 13473-01-3 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
General procedure: [0548] At -78 C., LDA (2 molar in THFheptane/ethylbenzene)was added to a solution of the appropriate pyridinederivative in THF (3 ml/mmol), the mixture was stirred for2-4 h and triisopropyl borate was then added quickly. Thereaction mixture was maintained at -7S C. for a further 2-3hand then slowly thawed to RT overnight. After addition ofwater, the THF was removed under reduced pressure and theaqueous phase was extracted twice with ethyl acetate Theaqueous phase was acidified with 2M hydrochloric acid, generallyresulting in formation of a precipitate which was filteredoff, washed with water and dried. The aqueous phasewas extracted three times with ethyl acetate. The combinedorganic phases were dried (sodium sulphate), filtered andconcentrated under reduced pressure.
  • 2
  • [ 13473-01-3 ]
  • [ 1427190-91-7 ]
  • [ 1427175-00-5 ]
  • 3
  • [ 13473-01-3 ]
  • [ 5419-55-6 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
10.44 g With lithium hexamethyldisilazane; In tetrahydrofuran; n-heptane; ethylbenzene; at -78 - 20℃; General procedure: General Method 1A: Preparation of a boronic acid At-78C, LDA (2 molar in THF/heptane/ethylbenzene) was added to a solution of theappropriate pyridine derivative in THF (3 ml/mmol), the mixture was stirred for2-4 h and triisopropyl borate was then added quickly. The reaction mixture wasmaintained at -78 C for a further 2-3 h and then slowly thawed to RT overnight.After addition of water, the THF was removed under reduced pressure and theaqueous phase was extracted twice with ethyl acetate The aqueous phase wasacidified with 2M hydrochloric acid, generally resulting in formation of aprecipitate which was filtered off, washed with water and dried. The aqueousphase was extracted three times with ethyl acetate. The combined organic phaseswere dried (sodium sulphate), filtered and concentrated under reduced pressure.10.0 g (69.65 mmol) of 5-chloro-2-methoxypyridine werereacted according to General Method 1A.The desired product precipitated on acidification with hydrochloric acid (2N).Yield: 10.44 g (purity 91%, 73% of theory)
10.0 g of 5-chloro-2-methoxypyridine were initially charged in 225 ml of THF, and 41.8 ml (83.6 mmol) of lithium diisopropylamide (2M in THF/heptane/ethylbenzene) were added at -78 C. The mixture was stirred at -78 C. for 4 h, and 32.6 ml (141 mmol) of triisopropyl borate were then added rapidly. The reaction mixture was stirred at-78 C. for 3 h and then warmed to room temperature overnight. The procedure was then repeated, and a further 20.9 ml (41.8 mmol) of lithium diisopropylamide (2M in THF/heptane/ethylbenzene) and 16.1 ml (69.7 mmol) of triisopropyl borate were added. The reaction mixture was poured into 500 ml of water and THF was removed under reduced pressure. The aqueous phase was extracted three times with ethyl acetate. The aqueous phase was acidified with hydrochloric acid (2N) and the precipitate was filtered oil. The filtrate was extracted twice with ethyl acetate, the organic phase was dried and filtered, the solvent was removed under reduced pressure and the residue, together with the precipitate, was dried under high vacuum. Yield:10.4 g (91% pure, 73% of theory).j0675] LC/MS [Method 1]: R=0.50 mm; MS (ESIpos):mlz=188 (M+H), j0676] ?H-NMR (400 MHz, DMSO-d5): oe [ppm]=8.64(br. s, 2H), 8.12 (s, 1H), 6.81 (s, 1H), 3.82 (s, 3H).
16 g Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 17 g of 5-chloro-2-methoxypyridine was added and cooled to -30C.A solution of 70 mL of 2.0 M of n-BuLi was slowly added dropwise, and after stirring for 30 minutes, 1,3 g of 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane was slowly added dropwise.After 2 hours of incubation, 41 mL of triisopropyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly raised to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 6-chloro-2-methoxy-4-pyridine boronic acid 16 g,
  • 4
  • [ 13473-01-3 ]
  • [ 121-43-7 ]
  • [ 475275-69-5 ]
YieldReaction ConditionsOperation in experiment
16 g Under a nitrogen atmosphere, 300 g of anhydrous tetrahydrofuran was added to the reaction flask, stirring was continued, 17 g of 5-chloro-2-methoxypyridine was added and cooled to -30C.Sulfur was added dropwise to 70 mL of 2.0 M of n-BuLi. After stirring for 30 minutes, 26 g of 1,4,7-trimethyl-1,4,7-triazacyclononane was slowly added dropwise.After incubation for 2 hours, 26 mL of trimethyl borate was slowly added dropwise at -30 C, stirred for 1 hr, slowly rose to room temperature and stirred for 1 hour.And 400 g of concentrated hydrochloric acid was added thereto, followed by stirring for 1 hour to carry out a hydrolysis reaction.The layers were allowed to stand, and the organic layer was washed three times with water (3 x 100 g).The aqueous layers were combined and the aqueous layer was extracted once with 100 ml of petroleum ether. The combined organic layers were dried over 50 g of anhydrous sodium sulfate and filtered.The filtrate was concentrated to dryness to give 16 g of product 5-chloro-2-methoxy-4-pyridine boronic acid.
  • 5
  • [ 13473-01-3 ]
  • [ 4214-79-3 ]
YieldReaction ConditionsOperation in experiment
73% With L-Selectride; In tetrahydrofuran; for 3.5h;Reflux; Inert atmosphere; General procedure: Toa solution of 1 (1.00 mmol) in THF (7.0 mL) was added L-selectride(1 M in THF, 3.0 mL, 3.00 mmol, 3 equiv) under an argonatmosphere. After being refluxed and monitored by TLC, thereaction mixture was quenched with MeOH and evaporated invacuo. The residue was purified by silica gel column chromatographyto give the desired compound 2.
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