[ CAS No. 32774-29-1 ]

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CAS No. 32774-29-1, is an indoles compound, with a molecular weight of 240.10, molecular formula C10H10BrNO, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Product Details

CAS No. :32774-29-1MDL No. :MFCD00130167
Formula :C10H10BrNOInChI Key :ZENXDUDCTZLSRP-UHFFFAOYSA-N
M.W :240.10Pubchem ID :122956
Boiling Point :411.5буC at 760 mmHg
Synonyms :

Computed Properties

TPSA : 36 H-Bond Acceptor Count : 1
XLogP3 : - H-Bond Donor Count : 2
SP3 : 0.20 Rotatable Bond Count : 2

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 32774-29-1 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
83%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.50 h;
Stage #2: With water; sodium sulfate In tetrahydrofuran at 0℃;
2-(5-Bromo-lflr-indol-3-yl)ethanol (13). The method of Bascop, S. L;Laronze, J. Y.; Sapi, J. Synthesis of 2-aminopropyle-3-indole-acetic(propionic) acid derivatives. ARKIVOC 2003, 46-61, was followed. To a solution of ester 12 (4 mmol, 1 equiv) in anhydrous THF (50 mL) was added lithium aluminium hydride (LiAlH4; 16 mmol, 4 equiv) in portions with the temperature maintained at 0 °C. The reaction mixture was brought to room temperature and stirred for 30 min. Excess LiAlH4 was destroyed by careful addition of a saturated aqueous solution of Na2SO4 with the temperature maintained at about 0 0C. The mixture was filtered and the filtrate washed with THF. The combined filtrates were concentrated under reduced pressure, the residue was acidified to pH 6 with 10 percent HCl and extracted with CHCl3. The combined organic layer was dried (anhydrous Na2SO4), filtered, evaporated to dryness and purified using flash column chromatography by elution with EtOAc/hexane to give the alcohol 13. Yield: 83 percent; 1H NMR (300 MHz, CDCl3): δ 2.97 (t, J = 18 Hz, 2 H), 3.86-3.93 (m, 2 H), 4.09 (t, J = 21 Hz,l H), 7.09 (d, J= 3 Hz, 1 H), 7.22 (d, J= 9 Hz, 1 H), 7.75 (s, 1 H), 8.10 (s, 1 H); MS (APCI): mlz 241.2 [M + H]+.
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 6838 - 6850
[2] Patent: WO2011/14128, 2011, A1. Location in patent: Page/Page column 65
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Reference: [1] Patent: US6399616, 2002, B1
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Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1810 - 1827
[2] Patent: WO2011/14128, 2011, A1
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Reference: [1] Chemical Communications, 2014, vol. 50, # 10, p. 1231 - 1233
[2] Organic Letters, 2017, vol. 19, # 7, p. 1504 - 1507
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Reference: [1] Chemical Communications, 2014, vol. 50, # 10, p. 1231 - 1233
[2] Organic Letters, 2017, vol. 19, # 7, p. 1504 - 1507
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Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 49, p. 12910 - 12914[2] Angew. Chem., 2013, vol. 125, # 49, p. 13148 - 13152,5
[3] Journal of the American Chemical Society, 2018, vol. 140, # 21, p. 6710 - 6717
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Reference: [1] Chemical Communications, 2014, vol. 50, # 10, p. 1231 - 1233
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