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CAS No. : | 1028432-04-3 | MDL No. : | MFCD11976059 |
Formula : | C13H23NO3SSi | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XWGSCRBSSWZLBD-UHFFFAOYSA-N |
M.W : | 301.48 | Pubchem ID : | 24899640 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3259 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.833333h; Inert atmosphere; | |
97% | Stage #1: 4-nitrobenzyl chloride; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
100% | Stage #1: hex-5-en-2-yn-1-ol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
99% | Stage #1: 3-Phenyl-1-propanol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; | |
87% | With (phthalocyaninato)iron(II); ethyl 2-(4-cyanophenyl)hydrazinecarboxylate; triphenylphosphine In toluene at 20℃; for 60h; Molecular sieve; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
91% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1-phenyl-3-butanol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.33333h; Inert atmosphere; | ||
With caesium carbonate In N,N-dimethyl-formamide at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 40℃; Inert atmosphere; | |
99% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1-mesitylethanol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 40℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere; | ||
With caesium carbonate In N,N-dimethyl-formamide at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1.5h; Inert atmosphere; | ||
With caesium carbonate In N,N-dimethyl-formamide at 60℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
97% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 7-(phenylseleno)heptan-1-ol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
100% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 4-(oxiran-2-yl)butyl acetate With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; | |
91% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 4-Methoxybenzyl alcohol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.0833333h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1.25h; Inert atmosphere; | |
84% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24.6 g | In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 25℃; Inert atmosphere; | |
91% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 25℃; for 2h; Inert atmosphere; | 16 [0153] To a solution of 4-thienoylfuroxan-3 -methanol (17) (0.5 g, 2.21 mmol) N-(t- butyldimethylsilyloxy)-4-methylbenzenesulfonamide (0.61 g, 2.01 mmol), and triphenylphosphine (1.05 g, 4.02 mmol) in toluene (7.5 mL) and THF (2.5 mL) was added dropwise DEAD (0.84 ml, 2.11 mmol) at 0 0C. The reaction mixture was allowed to attain room temperature in 2 h. The reaction mixture was diluted with ethyl acetate, successively washed with water, saturated NaHCO3, brine and dried (MgSO4). The crude product was purified on a 50 g Biotage silica gel column. Gradient elution with ethyl acetate (2→40%) in hexanes gave the product 18 as white solid: yield 0.93g (1.83 mmol, 91 %). 1H NMR (CDCl3) δ 0.22 (s, 6H, CH3), 0.88 (s, 9H, CH3), 2.49 (s, 3H, CH3), 4.30 (s, 2H, CH2) 7.27 (dd, J= 5.0 Hz and 3.8 Hz, IH, Het-H), 7.39 (d, J= 8.4 Hz, 2H, Ar-H), 7.76 (d, J= 8.4 Hz, 2H, Ar-H), 7.91 (dd, J= 5.0 Hz and 1.0 Hz, IH, Het-H) and 8.31 (dd, J= 4.0 Hz and 1.2 Hz, IH, Het-H); 13C NMR (CDCl3) δ ^l.9, 17.9, 21.7, 25.8, 47.8, 110.7, 128.2, 129.1, 129.5, 130.5, 137.5, 137.6, 140.4, 145.6, 153.6 and 175.1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 °C 2: trifluorormethanesulfonic acid / dichloromethane; water; acetonitrile / 1 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0 °C 2: trifluorormethanesulfonic acid / dichloromethane; water; acetonitrile / 1 h / 0 °C 3: [Au(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)(NTf2)] / toluene / 1 h / 60 °C / Molecular sieve |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With manganese(IV) oxide; 2-(2-(4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole; copper(II) bis(trifluoromethanesulfonate) In toluene at 120℃; for 24h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; 3-Phenylpropenol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Stage #1: methyl lactate; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; C16H24O3 With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; (Z)-4-benzyloxy-but-2-en-1-ol With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: 3-nonene-1-ol; N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; acetic acid 4-hydroxybut-2-enyl ester With triphenylphosphine In tetrahydrofuran; toluene for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: With diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 10℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | Stage #1: tert-butyldimethylsilyl chloride With hydroxylamine hydrochloride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Stage #2: With triethylamine In N,N-dimethyl-formamide at 10℃; Stage #3: p-toluenesulfonyl chloride In N,N-dimethyl-formamide at 10℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; for 0.0833333h; | 23 N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide 46 To a solution of alcohol 45 (400 mg, 1.32 mmol) in anhydrous toluene (4 mL) and THF (1.2 mL), N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide (397 mg, 1.32 mmol) and PPh3 (691 mg, 2.63 mmol) were added. The mixture was cooled to 0 °C and treated dropwise with DEAD (40% solution in toluene, 0.86 mL, 1.98 mmol). The reaction mixture was stirred at room temperature for 5 min, concentrated at reduced pressure and purified through column chromatography (35-70 μm silica gel, hexane/EtOAc mixtures, gradient elution). On elution with hexane/EtOAc 90:10, slightly impure 46 (913 mg) was isolated; Rf 0.60 (hexane/EtOAc 1:1); mp 91-92 °C; IR (ATR) N-(tert-butyldimethylsilyloxy)-N-[3-(6-chloro-2-(2-thienyl)quinolin-3-yl)propyl]-4-methylbenzenesulfonamide 46 ν 1594, 1548, 1522 (Ar-C-C and Ar-C-N st), 1359, 1168 (SO2) cm-1; 1H NMR (400 MHz, CDCl3) δ 0.09 [s, 6H, Si(CH3)2], 0.72 [s, 9H, Si[C(CH3)3]], 1.80 (tt, J = J' = 7.4 Hz, 2H, 2-H2), 2.25 (s, 3H, tosyl CH3), 2.81 (t, J = 7.2 Hz, 2H), 2.90 (t, J = 7.6 Hz, 2H) (1-H2 and 3-H2), 6.97 (dd, J = 4.8 Hz, J' = 4.0 Hz, 1H, 4"-H), 7.09-7.18 (complex signal), 7.20-7.24 (complex signal) [4H, 3"-H, 5"-H, and tosyl-C3(5)-H], 7.42 (dd, J = 9.2 Hz, J' = 2.0 Hz, 1H, 7'-H), 7.51 [br d, J = 8.4 Hz, 2H, tosyl-C2(6)-H], 7.57 (d, J = 2.0 Hz, 1H, 5'-H), 7.74 (s, 1H, 4'-H), 7.85 (d, J = 9.2 Hz, 1H, 8'-H); 13C NMR (100.6 MHz, CDCl3) δ - 4.1 [2CH3, Si(CH3)3], 18.4 [C, SiC(CH3)3], 21.8 (CH3, tosyl CH3), 26.1 [3CH3, SiC(CH3)3], 27.3 (CH2, C2), 30.8 (CH2, C3), 55.4 (CH2, C1), significant aromatic signals: 125.7 (CH, C8'), 129.5 [2CH, tosyl-C3(5)], 130.0 [2CH, tosyl-C2(6)], 132.4 (C), 132.8 (C) (C6', C8a'), 136.0 (CH, C4'), 144.8 (C, C3'), 152.9 (C, C2'); HRMS (ESI), calcd for [C29H3535ClN2O3S2Si + H+] 587.1620, found 587.1596. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C | ||
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 3: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere | ||
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C 3: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: silver fluoride / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -78 - 20 °C / Molecular sieve 2: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - 20℃; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With caesium carbonate In N,N-dimethyl-formamide for 17h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: 1 h 4: tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane; triethylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere; Sealed tube | ||
Multi-step reaction with 4 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C 4: tris-(dibenzylideneacetone)dipalladium(0); tris<3,5-bis(trifluoromethyl)phenyl>phosphane; triethylamine / N,N-dimethyl-formamide / 80 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: triethylamine / dichloromethane / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 17 h 2: pyridine hydrogenfluoride / tetrahydrofuran / 20 °C 3: 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: caesium carbonate / acetonitrile / 2 h / 20 °C / Inert atmosphere 2.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.33 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: caesium carbonate / acetonitrile / 2 h / 20 °C / Inert atmosphere 2.1: ethylmagnesium bromide / tetrahydrofuran; diethyl ether / 0.33 h / 0 - 20 °C / Inert atmosphere 2.2: 0.5 h / 0 °C / Inert atmosphere 3.1: palladium 10% on activated carbon; quinoline; hydrogen / ethanol; ethyl acetate / 1.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96.5% | With caesium carbonate In acetonitrile at 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 0.5h; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -90 - 20℃; Molecular sieve; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.17 h / 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2: sodium methylate / methanol / 5 h / 20 °C 3: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -78 °C / Molecular sieve; Inert atmosphere 2.1: sodium methylate / methanol / 5 h / 20 °C 3.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4.1: hydrazine hydrate / chloroform; methanol / 3 h / 0 - 20 °C 4.2: 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0℃; for 0.166667h; Inert atmosphere; | 3-(Inden-2-yl)but-2-enal oxime (13) DEAD (40% in toluene, 0.15 mL, 0.32 mmol) was added slowly to a mixture of 2-alkenylindole 11 (150 mg, 0.81 mmol), O-TBS-N-tosylhydroxylamine (218 mg, 0.72mmol), and PPh3 (424 mg, 1.62 mmol) in toluene (6 mL) and THF (2 mL) at 0 °C. After stirring at the temperature for 10 min, the solvent was evaporated to half an amount. The mixture was dissolved in MeCN (10 mL), and CsF (245 mg, 1.62 mmol) was added. After stirring at rt for 1 h, saturated NH4Cl aq.was added and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane (3:7, v/v)as an eluent to give the oxime 13 (123 mg, 76%) as yellow solid. 1H-NMR (CDCl3) δ: 8.23 (2/3H, d, J = 10.4 Hz), 7.61 (1/3H, d, J = 10.4 Hz), 7.46 (1/3H, d, J = 7.2 Hz), 7.42 (2/3H, d, J = 7.2 Hz), 7.41 (1H/3, d,J = 7.2 Hz), 7.36 (2/3H, d, J = 7.2 Hz), 7.30 (1/3H, t, J = 7.2 Hz), 7.27 (1/3H, t, J = 7.2 Hz), 7.23 (2/3H, d,J = 7.2 Hz), 7.19 (2/3H, d, J = 7.2 Hz), 7.00 (2/3H, s), 6.98 (1/3H, s), 6.72 (1/3H, d, J = 10.4 Hz), 6.43(2/3H, d, J = 10.4 Hz), 3.64 (4/3H, s), 3.63 (2/3H, s), 2.20 (3/3H, s), 2.18 (6/3H, s), one proton (OH) wasnot observed. MS m/z: 199 (M+). HRMS (EI) calcd for C13H13NO 199.0997; found 199.0988. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide; C8H6ClN3O2 With potassium carbonate; sodium iodide In acetonitrile at 20℃; Stage #2: With dmap In dichloromethane at 20℃; |