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[ CAS No. 92670-29-6 ] {[proInfo.proName]}

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Chemical Structure| 92670-29-6
Chemical Structure| 92670-29-6
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CAS No. :92670-29-6 MDL No. :
Formula : C9H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 164.20 Pubchem ID :-
Synonyms :

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* 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.

  • Downstream synthetic route of [ 92670-29-6 ]

[ 92670-29-6 ] Synthesis Path-Downstream   1~9

  • 2
  • [ 110-91-8 ]
  • [ 626-60-8 ]
  • [ 92670-29-6 ]
YieldReaction ConditionsOperation in experiment
99% With (C5H5)Fe(C5H3C(CH3)NC6H4CH3)PdCl(CN2(C6H3(CH(CH3)2)2)2C2H2); potassium-t-butoxide In 1,4-dioxane at 110℃; for 1h; Inert atmosphere; Schlenk technique;
99% With (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene)Pd(cinnamyl, 3-phenylallyl)Cl; sodium tertiary butoxide In neat (no solvent) at 110℃; for 12h; Inert atmosphere; Green chemistry;
99% With C28H29Cl2N3OPd; potassium-t-butoxide In toluene at 110℃; for 15h; Schlenk technique; Inert atmosphere; General procedure for the catalytic amination General procedure: A Schlenk ask was charged with the required aryl chloride (0.25 mmol), amine (0.30 mmol), N-heterocyclic carbene-palladium(II) complex (2 mol%), KOtBu (1.3 equiv), and toluene (0.5 mL). The mixture was stirred at 110 C for 15 h under N2. After cooling, the mixture was evaporated and the product was isolated by preparative TLC on silica gel plates. The puried products were identied by 1H NMR spectra, and their analytical data are given in the Supporting Information.
99% With tris-(dibenzylideneacetone)dipalladium(0); Cy*Phine; sodium tertiary butoxide In tetrahydrofuran at 100℃; for 15h; Sealed tube;
98% With 1-C10H7Ni(P(C6H5)3)2Br; potassium-t-butoxide; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In toluene at 23℃; for 24h; Inert atmosphere; General procedure for the room-temperature amination of (hetero)aryl halides catalyzed by the Ni(II)-(ς-aryl) complex/NHC/KOtBu. An oven-dried 25-mL three-necked flask was charged with KOtBu (4 mmol), Ni(PPh3)2(1-naphthyl)Cl (C-1) (0.05 mmol) and IPr*HCl (0.05 mmol). Then the aryl or heteroaryl halide (1 mmol) if solid and amine if solid (3 mmol) were added. The flask was evacuated and backfilled with nitrogen, with the operation being repeated twice. The halide and amine if liquid, dried toluene (5 ml) were added via syringe at this time. The reaction mixture was stirred at room temperature for 24 h, and filtered through a silica-gel pad that was washed with ethyl acetate. The combined organic phases were evaporated under reduced pressure and the residue purified by silica-gel column chromatography to give the desired product.
98% With C48H56ClN3Pd; potassium-t-butoxide In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;
97% With tris((1E,4E)-1,5- diphenylpenta-1,4-dien-3-one) dipalladium; potassium-t-butoxide; 1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride In 1,4-dioxane at 100℃; for 3h;
96% With palladium diacetate; sodium tertiary butoxide; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In toluene at 110℃; for 2h; Inert atmosphere;
96% With C46H52Cl3N3O2Pd; potassium 2-methyl-2-butoxide In toluene at 100℃; for 2h; Sealed tube;
95% With sodium tertiary butoxide In toluene at 100 - 110℃; for 20h; Inert atmosphere; Sealed vial;
95% With PdCl2(C3H3N2(CH3))(C3H2N2(C6H3(C3H7)2)2); potassium-t-butoxide In 1,4-dioxane at 70℃; for 3h; Inert atmosphere; 4.3. General procedure for the NHC-Pd(II)-Im catalyzed amination reactions of morpholine with aryl chlorides General procedure: Under N2 atmosphere, KOtBu (1.0 mmol), NHC-Pd(II)-Im 2a (1.0 mol %), dry dioxane (1.0 mL), morpholine 3 (0.8 mmol), and aryl chloride 4 (0.7 mmol) were successively added into a Schlenk reaction tube. The mixture was stirred at 70 °C for 3 h. The solvent was removed under reduced pressure and the residue was purified by a flash chromatograph on silica gel to give the pure products 5.
95% With C36H45Cl2N3OPd; potassium-t-butoxide In 1,4-dioxane at 90℃; for 1h; Inert atmosphere; Schlenk technique;
95% With palladium diacetate; sodium tertiary butoxide; dicyclohexyl(2′,6′-diisopropoxy-[1,1′-biphenyl]-2-yl)phosphine In neat (no solvent) at 110℃; for 12h; Green chemistry;
93% With Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazole-2-ylidene In Dimethyl ether at 20℃; for 20h;
93% With potassium-t-butoxide; [bis-1,3-(2,4,6-triisopropylbenzyl)-5,6-dimethylbenzimidazol-2-ylidene]-N-(3-Chloropyridine)dichloropalladium(II) In toluene at 90℃; for 3h;
92% With C42H46ClF6N3OPd; sodium tertiary butoxide In 1,4-dioxane at 80℃; for 0.75h;
92% With 5-(di-tert-butylphosphino)-1′,3′,5′-triphenyl-1′H-[1,4′]bipyrazole; tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide at 100 - 103℃; for 4h; Inert atmosphere;
91% With tris-(dibenzylideneacetone)dipalladium(0); C36H41P; sodium tertiary butoxide In decane; toluene at 100℃; for 2h; Inert atmosphere;
90% With tris((1E,4E)-1,5- diphenylpenta-1,4-dien-3-one) dipalladium; sodium tertiary butoxide; 2,8,9-tris(2-methylpropyl)-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane In toluene Heating;
90% With [Pd(SIPr)(η3-cin)Cl]; potassium-t-butoxide In 1,2-dimethoxyethane at 20℃; for 0.0833333h; Inert atmosphere;
88% With (N,N'-diarylimidazol-2-ylidene)-based palladacycle; sodium tertiary butoxide In 1,4-dioxane at 70℃; for 2h;
88% With sodium tertiary butoxide In toluene at 100℃; for 20h;
88% With potassium-t-butoxide In 1,2-dimethoxyethane at 50℃; for 4h;
88% With sodium hydride; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride; <i>tert</i>-butyl alcohol In tetrahydrofuran at 65℃;
88% With potassium-t-butoxide; C39H55Cl2N3Pd In tetrahydrofuran at 70℃; for 6h; Sealed tube;
87% With 1,1'-bis(diphenylphosphanyl)ferrocene; bis(1,5-cyclooctadiene)nickel (0); sodium tertiary butoxide In toluene at 100℃; for 19h;
87% With potassium-t-butoxide In 1,2-dimethoxyethane at 20 - 50℃; for 4h; 32 Example 32 JV-(3-Pyridyl)morpholine (Table 4, entry 5)[0110] The above general procedure yielded, after flash chromatography on silica gel (pentane/MTBE, 80/20), 144 mg (88 %) of the title compound.1H NMR (400 MHz, CDCl3): δ 8.31 (s, IH, H5), 8.14-8.12 (m, IH, H1), 7.19-7.10 (m, 2H, H2 + H3), 3.88 (t, / = 4.4 Hz, 4H, 0-CH2), 3.19 (t, / = 4.4 Hz, 4H, N-CH2). 13C NMR (100 MHz, CDCl3): δ 146.9 (C, C4), 141.0 (CH, CAl), 138.3 (CH, CAt), 123.5 (CH, CAr), 122.0 (CH, CAr), 66.6 (CH2, 0-CH2), 48.6 (CH2, N-CH2).
87% With C46H56Cl2N3O2PPd; potassium-t-butoxide In 1,2-dimethoxyethane at 80℃; for 1h; Inert atmosphere; Glovebox; Sealed tube;
87% With potassium-t-butoxide; C66H92Cl3N3Pd In n-heptane at 100℃; for 4h;
86% With potassium-t-butoxide In 1,2-dimethoxyethane at 20℃; for 0.25h;
86% With dichloro(3-chloropyridinyl)(1,3-(diisopropylphenyl)-4,5-bis(dimethylamino)imidazol-2-ylidene)palladium(II); Cs2CO3 In 1,2-dimethoxyethane at 80℃; for 24h; Schlenk technique; Sealed tube; Inert atmosphere;
84% With potassium 2-methyl-2-butoxide In 1,2-dimethoxyethane at 80℃; for 1h;
83% With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di-1-adamantylphosphino)phenyl]morpholine; potassium hydroxide; sodium tertiary butoxide In water monomer at 110℃; for 36h; Inert atmosphere; chemoselective reaction;
83% With C36H27NOP2*CH3O3S(1-)*C12H10N(1-)*Pd(2+); sodium tertiary butoxide In 1,2-dimethoxyethane at 110℃; for 24h; Inert atmosphere; Sealed tube;
82% With tris-(dibenzylideneacetone)dipalladium(0); 3-(t-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; sodium tertiary butoxide In toluene at 110℃; Inert atmosphere;
81% With potassium hydroxide In 1,4-dioxane at 100℃; for 16h;
77% With [Pd(Amphos)(cinnamyl)Cl]; sodium tertiary butoxide In 1,4-dioxane for 17h; Reflux;
77% With (SIPr)PdCl2(TEA); potassium-t-butoxide In 1,2-dimethoxyethane at 50℃; for 3.5h; Inert atmosphere;
71% With palladium diacetate; biphenyl-2-yl-di-tert-butyl-phosphane; sodium tertiary butoxide In toluene at 110℃; for 22h;
71% With (IPr)Ni(π-allyl)Cl; sodium tertiary butoxide In tetrahydrofuran at 25℃; for 24h; Inert atmosphere;
69% With sodium tertiary butoxide In 1,2-dimethoxyethane at 90℃; for 12h;
69% With sodium tertiary butoxide In dimethyl sulfoxide at 110℃; for 12h;
58% With nickel(II) chloride ethylene glycol dimethyl ether complex; 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole; sodium tertiary butoxide; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride In tert-butyl methyl ether at 80℃; for 3h; Green chemistry;
43% With tris-(dibenzylideneacetone)dipalladium(0); di(1-adamantyl)-4-(N,N-dimethyl)amino-phenyl-phosphane trifluoroacetic acid; sodium tertiary butoxide In toluene at 80℃; Sealed tube; Inert atmosphere;
41% With Ni(COD)(DQ); sodium tertiary butoxide; 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride at 100℃; for 24h; Sealed tube; Inert atmosphere;
30% With C29H37O2P; Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide In neat (no solvent) at 110℃; for 24h; Sealed tube; Inert atmosphere;
100 % Chromat. With (SIPr)Pd(cinnanmyl)Cl; potassium-t-butoxide In 1,2-dimethoxyethane at 20℃; for 0.0833333h;
With tris-(dibenzylideneacetone)dipalladium(0); 11-(dicyclohexylphosphino)-12-phenyl-9,10-dihydro-9,10-ethenoanthracene; sodium tertiary butoxide In toluene at 100℃; for 1h; Inert atmosphere;
With sodium tertiary butoxide In toluene at 100℃; for 1h; Inert atmosphere; 3.15 A flame-dried Schlenk flask was charged with tris(dibenzylideneacetone)palladium (4.6 mg, 0.005 mmol), 1 (4.4 mg, 0.025 mmol) or 6a (11.9 mg, 0.025 mmol), sodium terf-butoxide (134 mg, 1.40 mmol) and toluene (2.0 ml_) under nitrogen. Aryl bromide (1.00 mmol) and amine (1.10 mmol) were added and the resulting red solution heated at 800C with rapid stirring until reaction was complete, as judged by GC analysis. The reaction mixture was allowed to cool to room temperature, diluted with diethyl ether, passed through celite and the solvent removed to leave a yellow solid. Known products were characterised by NMR spectroscopy and mass spectrometry and unknown products by NMR spectroscopy, mass spectrometry and high resolution mass spectrometry (HRMS). The conversions were calculated using GC analysis as an average over three repeats.
With (η3-allyl)chloro(7,9-bis(2,6-diisopropylphenyl)-6b,9a-dihydroacenaphtho[1,2-d]imidazolidinylidene)palladium(II); potassium-t-butoxide In 1,4-dioxane at 20℃; for 1.5h; Inert atmosphere;
With [tert-butyloxy]bis(N,N-diisopropylamino)phosphane; Palladium(0) bis(dibenzylideneacetone); sodium tertiary butoxide In toluene at 105℃; for 4h; Inert atmosphere; Schlenk technique;

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  • 3
  • [ 110-91-8 ]
  • [ 1120-90-7 ]
  • [ 2767-91-1 ]
  • [ 92670-29-6 ]
  • 4
  • [ 110-91-8 ]
  • [ 7295-76-3 ]
  • [ 92670-29-6 ]
YieldReaction ConditionsOperation in experiment
61% With bis(1,5-cyclooctadiene)nickel(0); sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 100℃; for 12h; Inert atmosphere; Sealed vessel; III. Typical Procedure for Ni-Catalyzed Amination of N-Heteroaryl Methyl Ethers (Entry 1 in Table 2) General procedure: Ni(cod)2(27.5 mg, 0.1 mmol), 1,3-bis(2,6-diisopropylphenyl)imidazolium chloride (85.0 mg, 0.2 mmol), sodium tert-butoxide (288.3 mg, 3.0 mmol), 6-methoxyquinoline (1,79.6 mg, 0.5 mmol), morpholine (2, 217.8 mg, 2.5 mmol) and toluene (1.5 mL) were added to a 10 mL sample vial with a Teflon-sealed screwcap in a glovebox filled withnitrogen. After the cap was closed, the vial was stirred at 100 °C for 12 h. After cooling to room temperature, the crude mixture was filtered through a Celite pad. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (hexane/EtOAc = 1:1) to give 4-(quinolin-6-yl)morpholine (3, 58.9 mg, 74 %) as a white solid.
  • 5
  • [ 110-91-8 ]
  • [ 1211583-40-2 ]
  • [ 2767-91-1 ]
  • [ 92670-29-6 ]
  • 6
  • [ 109-00-2 ]
  • [ 2767-91-1 ]
  • [ 92670-29-6 ]
  • 7
  • [ 1413439-93-6 ]
  • [ 2767-91-1 ]
  • [ 92670-29-6 ]
  • 8
  • [ 1413439-80-1 ]
  • [ 2767-91-1 ]
  • [ 92670-29-6 ]
  • 9
  • [ 13368-42-8 ]
  • [ 3468-53-9 ]
  • [ 92670-29-6 ]
YieldReaction ConditionsOperation in experiment
77% With bis(1,5-cyclooctadiene)nickel(0); 1,2-bis-(dicyclohexylphosphino)ethane In toluene at 150℃; for 24h; Inert atmosphere;
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