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[ CAS No. 4382-54-1 ]

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2D
Chemical Structure| 4382-54-1
Chemical Structure| 4382-54-1
Structure of 4382-54-1 *Storage: {[proInfo.prStorage]}

Quality Control of [ 4382-54-1 ]

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Product Details of [ 4382-54-1 ]

CAS No. :4382-54-1MDL No. :MFCD00005614
Formula : C10H9NO3 Boiling Point : 447.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :191.18Pubchem ID :20401
Synonyms :

Computed Properties of [ 4382-54-1 ]

TPSA : 62.3 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.10 Rotatable Bond Count : 2

Safety of [ 4382-54-1 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4382-54-1 ]

  • Upstream synthesis route of [ 4382-54-1 ]
  • Downstream synthetic route of [ 4382-54-1 ]

[ 4382-54-1 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 4382-54-1 ]
  • [ 10601-19-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
  • 2
  • [ 124-38-9 ]
  • [ 169383-96-4 ]
  • [ 4382-54-1 ]
YieldReaction ConditionsOperation in experiment
80%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.166667 h;
Stage #2: With n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5 h;
Stage #3: at -20℃; for 0.5 h;
To a solution of 2-Bromo-5-methoxy-1H-indole (1.0 g,4.4 mmol, 1.0 equiv.) in dry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF(2.2 mL, 4.4 mmol, 1.0 equiv.) during 5 min. The clear solution was stirred at that temperature for anadditional 5 min, and a 2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was addeddropwise during 5 min, while maintaining the temperature below 20 C. The resulting mixture wasstirred at that temperature for 0.5 h, dry CO2 (0.20 g, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ®teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ®ltrate was concentratedand the residue was puri®ed by ash chromatography on silica gel (eluent: petroleum ether/ethylacetate = 3:1) to afford product 3f as brown solid, 0.68 g (yield: 80percent), m.p.: 199–201 C. 1H-NMR(600 MHz, DMSO) 7.36 (d, J = 8.9 Hz, 1H), 7.06 (d, J = 23.6 Hz, 2H), 6.90 (d, J = 8.8 Hz, 1H), 3.73 (s, 3H).13C-NMR (151 MHz, DMSO) 163.25, 154.31, 133.07, 129.10, 127.65, 116.28, 113.83, 107.47, 102.44, 55.61.
Reference: [1] Molecules, 2017, vol. 22, # 11,
  • 3
  • [ 4792-58-9 ]
  • [ 4382-54-1 ]
Reference: [1] European Journal of Medicinal Chemistry, 1990, vol. 25, # 3, p. 257 - 265
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] Gazzetta Chimica Italiana, 1958, vol. 88, p. 574,589
[4] Gazzetta Chimica Italiana, 1955, vol. 85, p. 1445,1447
[5] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 4
  • [ 67929-86-6 ]
  • [ 4382-54-1 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 25, p. 6270 - 6282
[2] Chemistry - A European Journal, 2012, vol. 18, # 16, p. 4859 - 4865
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 5
  • [ 104-94-9 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2243 - 2247
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 6
  • [ 4346-59-2 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[2] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
[3] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 7
  • [ 4792-56-7 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 8
  • [ 4792-57-8 ]
  • [ 4382-54-1 ]
Reference: [1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 214 - 220
  • 9
  • [ 18437-68-8 ]
  • [ 4382-54-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 6, p. 2243 - 2247
  • 10
  • [ 3471-32-7 ]
  • [ 4382-54-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 3, p. 950 - 954
  • 11
  • [ 82204-34-0 ]
  • [ 4382-54-1 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 313
  • 12
  • [ 4382-54-1 ]
  • [ 21778-81-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1987, vol. 30, # 11, p. 2074 - 2080
[2] Patent: US2003/181496, 2003, A1,
[3] Patent: EP1479384, 2004, A1,
[4] Chemical Communications, 2013, vol. 49, # 28, p. 2894 - 2896
[5] Journal of Medicinal Chemistry, 2015, vol. 58, # 5, p. 2489 - 2512
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