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[ CAS No. 944086-09-3 ]

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2D
Chemical Structure| 944086-09-3
Chemical Structure| 944086-09-3
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Product Details of [ 944086-09-3 ]

CAS No. :944086-09-3MDL No. :MFCD20528267
Formula : C10H8BrNO Boiling Point : -
Linear Structure Formula :-InChI Key :ZRGRITPJQJCAFA-UHFFFAOYSA-N
M.W :238.08Pubchem ID :16751572
Synonyms :

Computed Properties of [ 944086-09-3 ]

TPSA : 32.9 H-Bond Acceptor Count : 1
XLogP3 : 2.4 H-Bond Donor Count : 1
SP3 : 0.10 Rotatable Bond Count : 1

Safety of [ 944086-09-3 ]

Signal Word:WarningClassN/A
Precautionary Statements:P280-P305+P351+P338-P310UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 944086-09-3 ]

  • Upstream synthesis route of [ 944086-09-3 ]

[ 944086-09-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 51417-51-7 ]
  • [ 75-36-5 ]
  • [ 944086-09-3 ]
YieldReaction ConditionsOperation in experiment
93%
Stage #1: With diethylaluminium chloride In dichloromethane at 0℃; for 0.42 h;
Stage #2: at 0℃; for h;
Typical procedure 3 (See Scheme 2) (TP3):1 -(7-bromo-l -(3-chloroproρyO-l H-indol-3-yDethanone[0216] To a solution of 7-bromo-l //-indole (442 mg, 2.25 mmol) in dry CH2Cl2 (10 mL) at 0 0C was added Et2AlCl (3.4 mL, 1.0 M, 3.4 mmol) dropwise. The mixture was stirred at 0 0C for 25 min. A solution of AcCl (0.24 mL, 3.36 mmol) in CH2Cl2 (5 mL) was added dropwise and the mixture was stirred at 0 0C until TLC showed complete conversion of the indole (1-3 h). Saturated aqueous NaHCO3 (10 mL) was added slowly and the mixture was allowed to reach room temperature. The mixture was diluted with CH2Cb (60 mL) and the mixture was cautiously acidified to pH 4-5 with 2 M HCl (approx. 10 mL) to facilitate phase separation. The aqueous layer was extracted with CH2Cl2 (2x 10 mL) and the combined organic layers where washed with saturated aqueous NaHCψ3 and evaporated to dryness to give the acetylated compound (496 mg, 93percent). This acetyl ated crude product was dissolved in CH3CN (10 mL). To this solution was added Cs2CO3 (1.55 g, 4.76 mmol) and 1 - chloro-3-iodopropane (0.70 mL, 6.52 mmol) and the mixture was stirred at 50 0C overnight. The suspension was diluted with CH2Cl2 (70 mL), filtered and adsorbed onto celite. After purification by flash chromatography (heptanes - > heptanes: EtOAc 3:2) the title product was obtained (61 1 mg, 86percent over two steps. <n="78"/>[0217] 1H NMR (400 MHz, CDCl3) δ 8.41 (dd, J= 8.0, 1.1 Hz9 IH), 7.75 (s, IH), 7.44 (dd, J= 7.7, 1.1 Hz, IH), 7.12-7.08 (m, IH), 4.73 (t, J= 6.7 Hz, 2H), 3.50-3.47 (m, 2H), 2.50 (s, 3H), 2.39-2.33 (m, 2H).[0218] 13C NMR (100 MHz, CDCl3) δ 192.5, 137.7, 132.8, 129.7, 128.7, 123.7, 122.1, 1 16.5, 103.5, 45.8, 41.3, 34.1 , 27.5.
Reference: [1] Patent: WO2007/79239, 2007, A2. Location in patent: Page/Page column 75-76
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4474 - 4489
[3] Chemical Communications, 2017, vol. 53, # 28, p. 3945 - 3948
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1426 - 1436
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 702 - 707
  • 2
  • [ 51417-51-7 ]
  • [ 108-24-7 ]
  • [ 944086-09-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 793 - 801
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