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[ CAS No. 1075-26-9 ]

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Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 1075-26-9
Chemical Structure| 1075-26-9
Structure of 1075-26-9 *Storage: {[proInfo.prStorage]}

Quality Control of [ 1075-26-9 ]

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Product Details of [ 1075-26-9 ]

CAS No. :1075-26-9MDL No. :MFCD02179595
Formula : C9H9NO Boiling Point : 360.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :147.17Pubchem ID :-
Synonyms :

Computed Properties of [ 1075-26-9 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 1075-26-9 ]

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

Application In Synthesis of [ 1075-26-9 ]

  • Downstream synthetic route of [ 1075-26-9 ]

[ 1075-26-9 ] Synthesis Path-Downstream   1~10

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YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 3h;Under nitrogen; Preparation XLVII 6-((triisopropylsilyloxy)methyl)indole indole-6-carboxylic Acid Methyl Ester [0339] To a solution of indole-6-carboxylic acid (39.5 g, 245 mmol) in methanol (200 mL) and dichloromethane (750 mL) was added 2 M (trimethylsilyl)diazomethane in hexanes (160 mL, 320 mmol) dropwise over 1 hour. The reaction was stirred at room temperature overnight. The following day the reaction was concentrated to a thick brown crude oil that was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium bicarbonate (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The mixture was then filtered and the filtrate concentrated under reduced pressure to form a suspension. The suspension was filtered to provide 43 g of the desired compound as an off-white solid. [0340] <strong>[1075-26-9]6-(hydroxymethyl)indole</strong> [0341] To a solution of indole-6-carboxylic acid methyl ester (20.0 g, 114 mmol) in anhydrous tetrahydrofuran (1.6 L) stirring under nitrogen at room temperature was added carefully lithium aluminum hydride (8.7 g, 230 mmol) while purging with nitrogen. Following this addition, the reaction mixture was stirred at room temperature for 3 hours and was then cooled to 0 C. This mixture was treated sequentially with water (9 mL), 15% sodium hydroxide (9 mL), and additional water (25 mL). The resulting suspension was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 30%-60% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 16.0 g (95%) of the desired compound as an off-white solid. [0342] IS-MS, m/e 146.0 (m-1). [0343] Silylation [0344] To a solution of <strong>[1075-26-9]6-(hydroxymethyl)indole</strong> (16.0 g, 110 mmol) in dichloromethane (800 mL) stirring at 0 C. under nitrogen was added triethylamine (22.5 mL, 160 mmol). Next a prepared solution of triisopropylsilyl trifluoromethanesulfonate (30.5 mL, 115 mmol) in dichloromethane (200 mL) was added slowly using an addition funnel. The reaction was stirred at 0 C. for 3 hours. The reaction was then diluted with dichlormethane (200 mL) and washed with water (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was sujected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound. [0345] IS-MS, m/e 302 (m-1).
With hydrogenchloride; In tetrahydrofuran; sodium-dried tetrahydrofuran; water; EXAMPLE 9 6-Hydroxymethyl indole Lithium aluminium hydride (3.48 g, 91.70 mmol) was suspended in sodium-dried tetrahydrofuran (150 ml). The suspension was stirred under a nitrogen atmosphere. Methyl-(indol-6-yl)methanoate (8.0 g, 45.7 mmol) was dissolved in dry tetrahydrofuran (50 ml) and added dropwise to the lithium aluminium hydride suspension. The mixture was stirred at ambient temperature for three hours. Water (10 ml) was added dropwise, followed by 2N hydrogen chloride (30 ml). The mixture was extracted with diethyl ether (3*150 ml) to yield a light purple oil.
2.05 g To a suspension of lithium aluminium hydride (0.866 g; 22.82 mmol) in dry THF (30 mL) cooled at 0 C was added a solution of methyl 1 /-/-indole-6-carboxylate (2.000 g; 1 1 .42 mmol) in THF (30 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature overnight. The reaction was quenched by careful addition of a 1 N Rochelle salt solution. The reaction mixture was stirred at room temperature for 2 h and was then extracted with dichloromethane. The phases were separated. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure to afford 2.050 g of (1 /-/-indolyl-6-yl)methanol as a yellow oil which was used in the next step without further purification. ESI/APCI(-): 146 (M- H).
YieldReaction ConditionsOperation in experiment
With diisobutylaluminium hydride; In dichloromethane; at -78℃; for 2h; General procedure: TThhee ttiittllee c coommppoouunndd wwaass pprreeppaarreedd bbyy rreedduuccttiioonn ooff mmeetthhyyll 11--((((33--((ttrrilfflluuoorroommeetthhyyl})pphheennyyll))ssuullffoonnyyll 11 HH--iinnddoollee--55--ccaarrbbooxxyllaattee ((8800 mmgg,, 00..2211 mmmmooli)) wwiitthh DDIIBBAALL--HH 1 iivvll iinn DDCCMM ((441177 ppLL,, 00..4422 mmmmooii)) aaccccoorrddiinngg ttoo GGeenneerraall PPrroocceedduurree BB.. TThhee eexxttraraccttiioonn p prroovviiddeedd 7744 mmgg ( (9999%%)) ooff aa tthhee ttiittllee ccoommppoouunndd aass aa ccoolloorrlleessss ooiill wwhhiicchh wwaass uusseedd wwiitthhoouutt ffuurtrthheerr ppuuririffiiccaattiioonn;; 11HH NNMMRR ((440000MMHHzz,, MeeOODD)) deltadelta ~~ 88..1166 ( (ss,, 11 HH)),, 88..1133 ( (dd,, JJ == 88..11 HHzz,, 11 HH)),, 77..9977 ( (dd,, J J''~~ 88..66 HHzz,, 11 HH)),, 77..8844 ((dd,, JJ ~~ 88..33 HHzz,, 11 HH)),, 77..6668 ((dd,, JJ == 33..77 HHzz,, 11 H H)),, 77..6666 -- 77..6611 ((mm,, 11 H H)),, 77,.5511 ( (dddd,, JJ " 00..77,, 11 ..55 HHzz,, 11 HH)),, 77..3355 ( (dddd,, -J J ~ = ..33,, 88..66 HHzz,, 11 HH)),, 66..7733 ((dddd,, JJ == 00..99,, 33..77 HHzz,, 11 H H)),, 44..6633 ((ss,, 22 H H)).. General Procedure B* Reduction of methyl indole ester. To the solution of methyl N-sulfonyl indole ester f 1eq,) in anhydrous DCM (C: 0.2 mmol/mL) at -?8C was added dropwise a soiuiion of PIBAL-H at 1M in. DCM (2 eq.). The reaction was stirred at -78CC for 2h. The completion of the reaction was monitored by HPLC. Upon completion, H2O was added and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCOa, brine and dried over NaaS.CH. Filtration and removal of the solvent provided the desired product, which was used without further purification.
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