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CAS No. :41058-67-7 MDL No. :MFCD11935112
Formula : C12H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :WFPNMCKAQLBEMD-UHFFFAOYSA-N
M.W : 187.24 Pubchem ID :363343
Synonyms :

Safety of [ 41058-67-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 41058-67-7 ]

* 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 [ 41058-67-7 ]

[ 41058-67-7 ] Synthesis Path-Downstream   1~50

  • 1
  • spiro[cyclopentane-1,3'-indole]-2'-carbaldehyde-oxime [ No CAS ]
  • spiro[cyclopentane-1,3'-indole]-2'-carboxylic acid amide [ No CAS ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
With acetic anhydride
  • 2
  • [ 103490-49-9 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
74% With calcium hydride a) RT to 240 deg C, 2.5 h, b) 240 deg C, 30 min;
65% With quinoline; calcium oxide at 217 - 310℃; for 1.25h; b Step-b: Synthesis of spiro [cyclopentane- 1,3 -indolini -2-one: To a stined suspension of calcium oxide (2.75 g, 49 mmol) in quinoline (10 mL) wasadded N-phenylcyclopentanecarbohydrazide (1 g, 4.9 mmol). The mixture was heated to 270-310 °C for 75 mm. The reaction mixture was cooled to room temperature and 2M aqueous hydrochloric acid was added. The mixture was extracted with ethyl acetate and combined extracts were washed with 2M hydrochloric acid, brine and dried over Na2504. The obtained crude was purified by chromatography on silica gel (40-60% EtOAc in hexanes) to give thedesired product as an orange solid (0.6 g, 65%). ‘H NMR 400 MHz (DMSO-d6) ö 10.25 (bs, 1H),7.22 (d, J=7.2 Hz, 1H), 7.16-7.14 (m, 1H), 6.95-6.92 (m, 1H), 6.81 (d, J=7.2 Hz, 1H), 1.97-1.90(m, 6H), 1.76-1.71 (m, 2H); MS (ES) nile 188.1 (M+H).
With calcium oxide at 230 - 250℃;
  • 3
  • [ 98598-90-4 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
65% With sodium nitrite In acetic acid
  • 4
  • [ 4669-18-5 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
98% With boron trifluoride diethyl etherate In dichloromethane at 95℃; for 41h;
  • 5
  • [ 563-76-8 ]
  • [ 41058-67-7 ]
  • C15H16BrNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride In N,N-dimethyl-formamide at 70℃; for 1h;
  • 6
  • [ 108-30-5 ]
  • [ 41058-67-7 ]
  • [ 103490-50-2 ]
YieldReaction ConditionsOperation in experiment
25% With aluminium trichloride; N,N-dimethyl-formamide at 80℃; for 1h;
  • 7
  • [ 41058-67-7 ]
  • [ 7131-05-7 ]
YieldReaction ConditionsOperation in experiment
83% With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 75℃; for 1h;
With lithium aluminium hydride In tetrahydrofuran Inert atmosphere;
With lithium aluminium hydride In tetrahydrofuran at 20℃; for 2h; 1C.59.B Preparation of 2-(spiro[cyclopentane-1,3'-indolin]-1'-yl)ethanamine To a solution of spiro[cyclopentane-l,3'-indolin]-2'-one (35 mg, 0.187 mmol) in THF (lmL) was added lithium aluminum hydride (0.5 ml, 0.500 mmol). After stirring at room temperature for 2 h, the reaction was quenched with IN NaOH (2mL) and stirred for 10 min. The mixture was filtered off solids and extracted with EtOAc (3 x 2mL). The combined organics were washed with brine and dried over MgS04. The mixture was filtered by vacuum filtration and solvent was removed under reduced pressure to give 30 mg of crude indoline. To the crude intermediate was added 2-bromoethanamine hydrobromide (42.13 mg, 0.206 mmol). The neat mixture was heated to 120°C for 3 h. the mixture was purified by preparative HPLC to give the title compound (3 mg) as a TFA salt. LCMS m/z = 217.0 [M+H]+.
10 g With lithium aluminium hydride In tetrahydrofuran at 0 - 80℃; for 6h; 4(1).2 Step-2: Procedure for synthesis of spiro[cyclopentane-1,3'-indoline 4: [0215] To a solution of spiro[cyclopentane-1,3'-indolin]-2'-one 3 (1.3, 16 g, 85.5 mmol) in THF (200 mL) cooled at 0°C was added LiAlH4 (1.0 M in THF, 111 mL, 111.2 mmol) dropwise. The reaction mixture was stirred at room temperature for 4 h and refluxed at 80 °C for 2 hours, following which it was cooled to room temperature and quenched with saturated aq. Na2SO4 solution. The resulting slurry was filtered through a pad of Celite, the filtrate was washed with ethyl acetate and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography to afford spiro[cyclopentane-1,3'-indoline 4 (1.3, 10 g, 71%) as a yellowish powder. LCMS: 174.10 [M+H]+.

  • 8
  • [ 41058-67-7 ]
  • [ 98598-91-5 ]
YieldReaction ConditionsOperation in experiment
71% With Lawessons reagent In toluene Inert atmosphere; Reflux; Schlenk technique;
With Lawessons reagent In toluene
  • 11
  • [ 628-21-7 ]
  • [ 59-48-3 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
42% n-Butyl lithium (2.5 M in hexanes, 4.2 mL, 0.5 mmol) was added dropwise to a suspension of indolinone (0.665 mg, 5 mmol) and TMEDA (1.5 mL, 10 mmol) in THF (20 mL) at -78C in a dried flask under nitrogen. After 1 hour at -78C, 1,4- diiodobutane (3.3 mL, 25 mmol) was added dropwise and the mixture was allowed to slowly warm to rt. After 12 hours at rt, saturated aqueous ammonium chloride was added to the mixture and this mixture was extracted with EtOAc. The combined organic phases were washed with water, brine, dried over magnesium sulphate, filtered and concentrated in vacuo. Chromatography on silica (10-30% EtOAc in isohexane) gave isolation of the desired compound as a pale pink solid (393 mg, 2.1 mmol, 42%). ? NMR (400 MHz): delta 1.90 (m, 2H), 2.03 (m, 2H), 2.10 ( m, 2H), 2.21 (m, 2H), 6.94 ( m, 1H), 7.04 ( m, 1H), 7.20 (m, 2H), 8.75 ( bs, 1H). LC/MS 188 (MH+).
42% Preparatory Example 7 Spiro[cyclopentane-1,3'-indolin]-2'-one n-Butyl lithium (2.5 M in hexanes, 4.2 mL, 0.5 mmol) was added dropwise to a suspension of indolinone (0.665 mg, 5 mmol) and TMEDA (1.5 mL, 10 mmol) in THF (20 mL) at -78 C. in a dried flask under nitrogen. After 1 hour at -78 C., 1,4-diiodobutane (3.3 mL, 25 mmol) was added dropwise and the mixture was allowed to slowly warm to rt. After 12 hours at rt, saturated aqueous ammonium chloride was added to the mixture and this mixture was extracted with EtOAc. The combined organic phases were washed with water, brine, dried over magnesium sulphate, filtered and concentrated in vacuo. Chromatography on silica (10-30% EtOAc in isohexane) gave isolation of the desired compound as a pale pink solid (393 mg, 2.1 mmol, 42%). 1H NMR (400 MHz): delta 1.90 (m, 2H), 2.03 (m, 2H), 2.10 (m, 2H), 2.21 (m, 2H), 6.94 (m, 1H), 7.04 (m, 1H), 7.20 (m, 2H), 8.75 (bs, 1H). LC/MS 188 (MH+).
  • 12
  • [ 41058-67-7 ]
  • [ 304876-16-2 ]
YieldReaction ConditionsOperation in experiment
96% With bromine; sodium acetate; acetic acid
96% With bromine; sodium acetate In acetic acid for 0.5h; 5'-Bromospiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one 5-Bromo-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one A solution of spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water, dried (MgSO4), and evaporated to give the subtitled compound (0.37 g, 1.47 mmol, 96%) as an off-white solid which was used without further purification: 1H NMR (CDCl3) δ 1.8-2.27 (m, 8H), 6.79 (d, J=8 Hz, 1H), 7.30-7.39 (m, 2H), 8.63 (br s, 1H).
With bromine; sodium acetate; acetic acid at 20℃;
  • 13
  • [ 41058-67-7 ]
  • [ 304876-35-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: Br2; NaOAc; AcOH / 20 °C 2.1: NaH / tetrahydrofuran 2.2: n-BuLi; (iPrO)3B / tetrahydrofuran
  • 14
  • [ 41058-67-7 ]
  • [ 516517-55-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Br2; NaOAc; AcOH / 20 °C 2: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane; H2O / 90 °C
  • 15
  • [ 41058-67-7 ]
  • 5'-(3-Cyanophenyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Br2; NaOAc; AcOH / 20 °C 2.1: NaH / tetrahydrofuran 2.2: n-BuLi; (iPrO)3B / tetrahydrofuran 3.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane; H2O / 90 °C
  • 16
  • [ 41058-67-7 ]
  • 5'-(3-nitrophenyl)spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Br2; NaOAc; AcOH / 20 °C 2: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane; H2O / 90 °C
  • 17
  • [ 41058-67-7 ]
  • [ 304875-56-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: Br2; NaOAc; AcOH / 20 °C 2.1: NaH / tetrahydrofuran 2.2: n-BuLi; (iPrO)3B / tetrahydrofuran 3.1: Pd(PPh3)4; Na2CO3 / 1,2-dimethoxy-ethane; H2O / 90 °C
  • 18
  • [ 21905-78-2 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) NaH / 1.) DMF, 0 deg C, 20 min, 2.) DMF, RT, overnight 2: 92 percent / 4percent aq. NaOH / methanol / 0.5 h / 100 °C
  • 20
  • [ 41058-67-7 ]
  • 5'-{2-[4-(1,2-benzoisothiazol-3-yl)piperazinyl]ethyl}-3,3-spirocyclopentane-1,3-dihydro-2(1H)-indol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: AlCl3 / CS2 2: Et3SiH, CF3COOH 3: Na2CO3, NaI / various solvent(s) / 72 h / Heating
  • 21
  • [ 41058-67-7 ]
  • [ 107081-83-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 25 percent / AlCl3, DMF / 1 h / 80 °C 2: 37 percent / 85percent hydrazine hydrate / ethanol / 4 h / Heating
  • 22
  • [ 41058-67-7 ]
  • [ 122280-63-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AlCl3 / dimethylformamide / 1 h / 70 °C 2: acetonitrile / 2 h / Heating
6 5'-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-spiro[cyclopentane-1,3'-[3H]-indol]-2'(1'H)one STR53 EXAMPLE 6 5'-(3,6-Dihydro-6-methyl-2-oxo-2H-1,3,4-thiadiazin-5-yl)-spiro[cyclopentane-1,3'-[3H]-indol]-2'(1'H)one STR53 Starting from spiro[cyclopentane-1,3'-[2H]indol]-2'-one and following the procedure of Description 5 and Example 3, afforded the desired compound. m.p.=275° C. IR (KBr)ν=3,200; 1,705; 1,690; 1,620; 1,485; 1,240 cm-1. NMR (DMSO-d6)δ=1.61 ppm (d,3H,J=7.2 Hz,CH3: 2.00 (m,8H,cyclopentane); 4.36 (q,1H,J=7.2 Hz,CH); 7.00 (d,1H,J=8 Hz,Ar); 7.49 (d,1H,J=8 Hz,Ar); 7.65 (s,1H,Ar); 10.15 (s,1H,exch.D2 O,NH); 11.07 (s,1H,exch.D2 O,NH).
  • 23
  • [ 41058-67-7 ]
  • [ 98598-90-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Lawesson's reagent / toluene 2: 1.) sodium hydride / 2.) THF, room temp. 3: 72 percent / NH3 / methanol / 21 h / 140 °C
  • 24
  • [ 41058-67-7 ]
  • [ 98598-92-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Lawesson's reagent / toluene 2: 1.) sodium hydride / 2.) THF, room temp.
  • 25
  • [ 41058-67-7 ]
  • [ 98598-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Lawesson's reagent / toluene 2: 1.) sodium hydride / 2.) THF, room temp. 3: 72 percent / NH3 / methanol / 21 h / 140 °C 4: 1.) sodium hydride / 2.) THF
  • 26
  • [ 23077-27-2 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: acetic acid; water; sodium nitrite 2: acetic acid anhydride
  • 27
  • [ 871021-84-0 ]
  • [ 41058-67-7 ]
  • [ 908139-66-2 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 4-Nitrophenyl chloroformate; spiro[cyclopentane-1,3'-indol]-2'(1'H)-one With triethylamine In dichloromethane at 20℃; for 3h; Stage #2: tert-butyl 4-[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate In dichloromethane at 20℃; for 18h; 1.6 Step 6. tert-Butyl 4-[4-([(2'-oxospiro[cyclopentane-1,3'-indol]-1'(2'H)-yl)carbonyl]amino}methyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate To a stirred solution of spiro[cyclopentane-1,3'-indol]-2'(1'H)-one (600 mg, 3.2 mmol, Howard, Harry R. et al., J. Med. Chem., 1996, 39, 143) and triethylamine (972 mg, 9.6 mmol) in CH2Cl2 (20 mL) was added 4-nitrochloroformate (677 mg, 3.4 mmol) at room temperature, and stirred at ambient temperature for 3 h. Then, a solution of tert-butyl 4-[4-(aminomethyl)piperidin-1-yl]methyl}tetrahydro-2H-pyran-4-carboxylate (1.0 g, 3.2 mmol, step 5 of Example 1) in CH2Cl2 (5 mL) was added at room temperature, and stirred for 18 h. Then, sat. NaHCO3 aq. (20 mL) was added, extracted with CH2Cl2 (30 mL*3), dried over MgSO4, filtered and concentrated gave yellow brown oil. The residue was chromatographed on a column of aminopropyl-silica gel eluding with hexane/ethyl acetate (11:1) to give 1.3 g (75%) of the title compound as clear yellow oil. MS (ESI) m/z: 526 (M+H)+. 1H-NMR (CDCl3) δ: 8.70 (1H, br s), 8.23 (1H, d, J=8.1 Hz), 7.41-7.10 (3H, m), 3.83-3.75 (2H, m), 3.52-3.47 (2H, m), 3.29-3.20 (2H, m), 2.83-2.75 (2H, m), 2.44 (2H, s), 2.25-1.20 (28H, m).
  • 28
  • [ 41058-67-7 ]
  • 5-Bromo-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bromine; sodium acetate In acetic acid 13 5-Bromo-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one 5-Bromo-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one A solution of spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (*2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water, dried (MgSO4), and evaporated to give the title compound (0.37 g, 1.47 mmol, 96%) as an off-white solid which was used without further purification: 1H NMR (CDCl3) δ 1.8-2.27 (m, 8H), 6.79 (d, J=8 Hz, 1H), 7.30-7.39 (m, 2H), 8.63 (br s, 1H).
  • 29
  • [ 865-47-4 ]
  • [ 106-96-7 ]
  • [ 41058-67-7 ]
  • [ 125055-12-1 ]
YieldReaction ConditionsOperation in experiment
In <i>N</i>-methyl-acetamide; dichloromethane 123 1'-(2-propynyl)spiro[cyclopentane-1,3'-[3H]indol]-2'-(l'H)-one EXAMPLE 123 1'-(2-propynyl)spiro[cyclopentane-1,3'-[3H]indol]-2'-(l'H)-one Potassium tert.-butoxide, 0.37 g (3.3 mmol), was added to a solution of 0.56 g (3 mmol) of spiro[cyclopentane-1,3'[3H]indol]-2'-(1'H)-one [ref. R. J. Owellen, J. Org. Chem. 39, 69 (1974)]in 10 ml of dimethylformamide. The mixture was stirred for 15 minutes and 0 3 ml of propargyl bromide was added and stirring was continued for 30 minutes. The reaction mixture was then partitioned between xylene and saturated sodium bicarbonate solution. The organic phase was dried and evaporated and the residue was chromatographed over 20 g of silica gel using methylene chloride for elution. The combined clean fractions were evaporated and the residue was crystallized from ether/hexane to give colorless crystals of 1'-(2-propynyl)spiro[cyclopentane-1,3'-[3H]indol]-2'-(1'H)-one with m.p. 109°-111°.
  • 30
  • [ 3400-45-1 ]
  • [ 613-94-5 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
In methanol; water 2.B 5'-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one B. Preparation of spiro[cyclopentane-1,3'-[3H]indol]-2'(1'H)-one. A mixture a 5.0 g of cyclopentanecarboxylic acid, 2-phenylhydrazide and 1.64 g of calcium hydride was heated gradually to 240° C. over a 2.5 hour period. After heating at 240° C. for an additional 30 minutes, the mixture was cooled to room temperature. A solution of 20 ml of water and 50 ml of methanol was added dropwise to the residue. The resulting slurry was brought to pH 1 with concentrated hydrochloric acid, diluted with 50 ml of water, and brought to reflux for 20 minutes. The solution was cooled and brought to pH 3. The resulting precipitate was filtered and recrystallized from ethyl acetate/hexane to provide 1.3 g of the desired subtitle intermediate, m.p. 110°-111° C. Analysis for C12 H13 NO: Calculated: C, 76.98; H, 7.00; N, 7.48; Found: C, 76.69; H, 7.07; N, 7.24.
  • 31
  • [ 41058-67-7 ]
  • 5'-Chlorospiro(cyclopentane-1,3'-indoline)-2-one [ No CAS ]
  • [ 41058-52-0 ]
YieldReaction ConditionsOperation in experiment
In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; acetic acid 29.a a. a. 5'-Chlorospiro(cyclopentane-1,3'-indoline)-2-one Spiro(cyclopentane-1,3'-indoline)-2'-one (18,7 g; 0.10 moles) is dissolved in acetic acid (50 ml) containing 100 mg of ferricloride hexahydrate, cooled in ice-water and drop-wise treated under agitation with a solution of clorine in acetic acid (82 ml of a solution containing 7,8 g per 100 ml). After the addition air is blown through the solution to eliminate a possible excess of clorine as well as hydrogen cloride. The crystallized product (8.7 g) is sucked off and the filtrate is concentrated in vacuum, upon which an additional product quantity (7.3 g) is obtained. After recrystallization from ethanol the substance melts at 201° - 202°C. If an excess of clorine is used in this example there is obtained 5',7'-Dichlorospiro(cyclopentane-1,3'-indoline)-2'-one of m.p. 175° - 176°C.
  • 32
  • [ 19472-74-3 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium <i>tert</i>-butylate / tetrahydrofuran; 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 10 °C / Inert atmosphere 2.1: copper(l) iodide; N-acetylglycine; potassium iodide; sodium hydroxide / <i>tert</i>-butyl alcohol / 24 h / 100 °C
  • 33
  • [ 143328-17-0 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
92% With copper(l) iodide; N-acetylglycine; potassium iodide; sodium hydroxide In <i>tert</i>-butyl alcohol at 100℃; for 24h;
Multi-step reaction with 2 steps 1: sodium hydroxide; <i>tert</i>-butyl alcohol / 100 °C / Sealed tube 2: 1,2-diamino-benzene; copper(I) oxide; sodium t-butanolate / <i>tert</i>-butyl alcohol / 24 h / 100 °C / Sealed tube
Multi-step reaction with 3 steps 1.1: sodium hydroxide; <i>tert</i>-butyl alcohol / 100 °C / Sealed tube 2.1: sodium hydride / hexane; tetrahydrofuran / 1 h / 20 °C / Schlenk technique 2.2: 70 °C / Schlenk technique 3.1: 1,2-diamino-benzene; copper(I) oxide; sodium t-butanolate / <i>tert</i>-butyl alcohol / 24 h / 100 °C / Sealed tube
  • 34
  • [ 1422149-02-7 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
97% With copper(I) oxide; 1,2-diamino-benzene; sodium t-butanolate In <i>tert</i>-butyl alcohol at 100℃; for 24h; Sealed tube; Spiro[cyclopentane-1,3'-indolin]-2'-one (2h): General procedure: To a screw-capped vial (20-mL) were added CuI (0.005 mmol, 0.7 mg, 1.0 mol %), Benzene-1,2-diamine (0.01 mmol, 1.1 mg, 2.0 mol %), NaOtBu (1.5 mmol, 144.2 mg, 3.0 equiv) and amide 1 (0.5 mmol, 1.0 equiv) in t-BuOH (tert-butanol, 5.0 mL). The vial was sealed with cap and allowed to stir at 100 °C for the specific reaction time. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 2 were obtained according to this procedure. The known structures were characterized by the HRMS, 1H NMR and 13C NMR spectra of reported literatures. Spectral data, melting point, HRMS data and the copies of 1H NMR and 13C NMR spectra for all compounds are listed below.
  • 35
  • [ 1422148-74-0 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
97% With copper(I) oxide; 1,2-diamino-benzene; sodium t-butanolate In <i>tert</i>-butyl alcohol at 100℃; for 24h; Sealed tube; Spiro[cyclopentane-1,3'-indolin]-2'-one (2h): General procedure: To a screw-capped vial (20-mL) were added CuI (0.005 mmol, 0.7 mg, 1.0 mol %), Benzene-1,2-diamine (0.01 mmol, 1.1 mg, 2.0 mol %), NaOtBu (1.5 mmol, 144.2 mg, 3.0 equiv) and amide 1 (0.5 mmol, 1.0 equiv) in t-BuOH (tert-butanol, 5.0 mL). The vial was sealed with cap and allowed to stir at 100 °C for the specific reaction time. The crude reaction mixture was diluted with CH2Cl2, filtered through a thin Celite pad, and concentrated in vacuo. The residue was isolated through a column chromatography by using hexane and ethyl acetate as eluent to give the pure product. Products 2 were obtained according to this procedure. The known structures were characterized by the HRMS, 1H NMR and 13C NMR spectra of reported literatures. Spectral data, melting point, HRMS data and the copies of 1H NMR and 13C NMR spectra for all compounds are listed below.
Multi-step reaction with 2 steps 1.1: sodium hydride / hexane; tetrahydrofuran / 1 h / 20 °C / Schlenk technique 1.2: 70 °C / Schlenk technique 2.1: 1,2-diamino-benzene; copper(I) oxide; sodium t-butanolate / <i>tert</i>-butyl alcohol / 24 h / 100 °C / Sealed tube
  • 36
  • [ 110-52-1 ]
  • [ 59-48-3 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
29% Stage #1: 2-oxoindole With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 28h; Inert atmosphere; 28 LiHMDS (83 mL, 82.6 mmol, IM in THF) was added dropwise to a solution of oxindole (5 g, 37.6 mmol) in anhydrous THF (120 mL) under N2at -78 °C. The reaction mixture was stirred at -78 °C for 1 h. Then 1,4-dibromobutane (4.5 mL, 37.6 mmol) was added dropwise and the reaction mixture was stirred 1 h at -78 °C followed by 27 h at room temperature. The reaction mixture was evaporated to dryness, dissolved in EtOAc and washed with sat. aq. NH4CI (2x). The aqueous phase was extracted with EtOAc (2x) and the combined organic phases were dried over Na2SO4. The solids were removed by filtration and the filtrate was evaporated to dryness. The crude mixture was purified by flash chromatography on silica gel (10% to 25% EtOAc in CyH) to give spiro[cyclopentane-1,3'-indolin]-2'-one (2 g, 29%) as a white solid.1H-NMR (DMSO-d6, 300 MHz): 1.71-1.75 (m, 2H), 1.93-1.97 (m, 6H), 6.81 (d, J= 7.7 Hz, 1H), 6.93 (t, J = 7.5 Hz, 1H), 7.14 (t, J= 7.7 Hz, 1H), 7.21 (d, J= 13 Hz, 1H), 10.25 (br s, 1H) ppm. LC-MS: C12H13NO [M+H]+: 188.
With lithium hexamethyldisilazane Inert atmosphere;
0.20 g Stage #1: 2-oxoindole With lithium hexamethyldisilazane In tetrahydrofuran at -77℃; for 0.5h; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -77 - 20℃; for 3h; 1C.59.A Preparation of spiro[cyclopentane-1,3'-indolin]-2'-one A solution of indolin-2-one (1.0 g, 7.510 mmol) in THF (30 mL) was cooled to -77 °C and 1M LiHMDS (16.52mL, 16.52 mmol) was added. After stirring for 30 minutes 1,4-dibromobutane (1.784 g, 8.262 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred for an additional 3hours. The reaction was quenched with sat. NH4C1 (50mL) and extracted with EtOAc (2 x 30mL). The organics were dried over MgS04and filtered by vacuum filtration through a glass fiber paper. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (0-60% EtOAc in hexane) to give the title compound (0.20 g). LCMS m/z = 188.2[M+H]+; NMR (400 MHz, CDC13) δ ppm 1.83-1.91 (m, 2H), 1.92-2.02 (m, 2H), 2.03-2.12 (m, 2H), 2.14-2.23 (m, 2H), 6.85 (m, 1H), 7.02 (ddd, J = 7.9, 7.4, 1.0 Hz, 1H), 7.15-7.20 (m, 2H), 7.43 (bs, 1H).
Stage #1: 2-oxoindole With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -50℃; for 0.5h; Stage #2: 1,4-dibromo-butane In tetrahydrofuran at -78 - 20℃; for 3h; 4(1).1 Step-1: Procedure for synthesis of spiro[cyclopentane-1,3'-indolin]-2'-one 3: [0214] To a solution of indolin-2-one (1.1, 20 g, 150 mmol) in THF (200 mL) cooled to -78°C, was added LiHMDS (1.0 M in THF, 300 mL, 300 mmol) dropwise. It was slowly warmed to -50 °C and stirred for 30 min, followed by cooling to -78 °C and 1,5-dibromobutane (1.2, 35.7 g, 165 mmol) was added. The reaction mixture was stirred at room temperature for 3 h. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of reaction as monitored by TLC, the reaction mixture was quenched with saturated solution of ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to dryness to afford spiro[cyclopentane-1,3'-indolin]-2'-one 3 (1.3, 16 g, crude). This compound was used in the next step without further purification. LCMS: 188.0 [M+H]+.

  • 38
  • [ 41058-67-7 ]
  • 1-(2-(spiro[cyclopentane-1,3'-indoline]-1'-yl)phenyl)-3-(4-(trifluoromethoxy)phenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Inert atmosphere 2: neat (no solvent) / 175 °C / Inert atmosphere; Microwave irradiation 3: tin(II) chloride dihdyrate / ethyl acetate / 16 h / 23 °C / Inert atmosphere 4: dichloromethane / 16 h / 23 °C / Inert atmosphere
  • 40
  • [ 41058-67-7 ]
  • C14H20N2*2BrH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 20 °C 2: neat (no solvent) / 3 h / 120 °C
  • 41
  • [ 100-63-0 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / N,N-dimethyl-formamide / 1 h / 20 °C 2: calcium oxide; quinoline / 1.25 h / 217 - 310 °C
  • 42
  • [ 4524-93-0 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / N,N-dimethyl-formamide / 1 h / 20 °C 2: calcium oxide; quinoline / 1.25 h / 217 - 310 °C
  • 43
  • [ 41058-67-7 ]
  • 2'-oxospiro[cyclopentane-1,3'-indoline]-5'-sulfonylchloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chlorosulfonic acid at 20℃; for 1h; VIII Example-VIlI: Synthesis of N-(2-methoxyphenyl)-2-oxospiro[cyclopentane- 1,3 -indolinel -5- sulfonamide: (‘Compound-3 1’) A mixture of spiro[cyclopentane-1,3-indolin]-2-one (0.2 g, 1.06 mmol, step-b product of intermediate-2) in chioro suiphonic acid (2.5 mL) was stined at RT for lh. Then the reaction mixture was poured into cold water. The precipitate formed was filtered and dried under reducedpressure to get the solid. The obtained solid (2-oxospiro[cyclopentane-1,3-indoline]-5-sulfonyl chloride) (0.15 g, 0.525 mmol) was dissolved in DCM and added pyridine (1 mL), 2-methoxy aniline (0.07 1 g, 0.577 mmol). The reaction mixture was stined at RT for 16h. After completion of the reaction, the reaction mixture was evaporated completely to get the residue, and which was purified by preparative TLC (0.04 g, 10%). ‘H-NMR (400 MHz, CD3OD) ö 7.53-7.49 (m,1H), 7.389-7.383 (d, 1H), 7.25-7.22 (m, 1H), 7. 10-7.0 (m, 1H), 6.90-6.87 (m, 3H), 3.47(s, 3H),1.99-1.93 (m, 4H), 1.84-1.75 (m, 2H), 1.70-1.64 (m, 2H); LC-MS: mlz 371.1 (M-H).
  • 44
  • [ 41058-67-7 ]
  • N-(2-methoxyphenyl)-2'-oxospiro[cyclopentane-1,3'-indoline]-5'-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: chlorosulfonic acid / 1 h / 20 °C 2: pyridine / dichloromethane / 16 h / 20 °C
  • 45
  • [ 41058-67-7 ]
  • 5'-amino-7'-hydroxy-1'-(4-methoxybenzyl)spiro[cyclopentane-1,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: sulfuric acid; nitric acid / 0.5 h / -15 - 20 °C 2: N-Bromosuccinimide; sulfuric acid / 5 h / 20 °C 3: caesium carbonate / N,N-dimethyl-formamide / 3 h / 20 °C / Cooling with ice 4: tris-(dibenzylideneacetone)dipalladium(0); potassium hydroxide; tert-butyl XPhos / water; 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 5: ammonium chloride; iron / ethanol / 2 h / 100 °C
  • 46
  • [ 41058-67-7 ]
  • 5'-nitrospiro[cyclopentane-1,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With sulfuric acid; nitric acid at -15 - 20℃; for 0.5h; c Step-c: Synthesis of 5 -nitrospiro[cyclopentane- 1,3 -indolini -2-one: To a stined solution of Spiro[cyclopentane-1,3-indolin]-2-one (0.6 g) in 5.0 mL ofconcentrated sulfuric acid at -15 °C was added fuming nitric acid (0.2 mL) drop wise. Thereaction mixture was allowed stir at RT for 0.5h and then poured into ice water. A yellow precipitate formed was collected by filtration. The desired product obtained as a white solid. (0.5 g, 67%). This was taken as such to next step. ‘HNMR (400 MHz, DMSO-d6) ö 10.98 (bs, 1H),8.15 (dd, J=2.2 & 8.6 Hz, 1H), 8.09 (d, J=1.6 Hz, 1H), 7.01 (d, J=8.3 Hz, 1H), 1.99-1.91 (m,6H), 1.89-1.86 (m, 2H); MS (ES) m/e 233.2 (M+H).
  • 47
  • C17H21NO3 [ No CAS ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 5h; 11 Example 11: Compound 11 Trifluoroacetic acid (8 mL) was added to 11-1 (2 g, 6.96 mmol) in dichloromethane (50 mL) at 0 °C. The temperature was slowly raised to 20 °C to react for 5 hours. The reaction mixture was rotary-dried, and diluted with methylene chloride (100 mL). The diluted solution was washed with 5% aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate, filtered and evaporated to give the target compound 11-2. 1H NMR (400 MHz, CDCl3) δ 8.14 (br. s., 1H), 7.25 - 7.15 (m, 2H), 7.09 - 7.00 (m, 1H), 6.91 (d, J = 7.5 Hz, 1H), 2.28 - 2.16 (m, 2H), 2.15 - 1.84 (m, 6H).
  • 48
  • [ 41058-67-7 ]
  • 5'-hydroxyspiro[cyclopentane-1,3'-indolin]-2'-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene In chloroform at 20℃; for 1h; Inert atmosphere; 28 PIFA (5.23 g, 12.2 mmol) and TFA (7.5 mL, 101.47 mmol) were added to a solution of spiro[cyclopentane-1,3'-indolin]-2'-one (1.9 g, 10.2 mmol) in chloroform (120 mL) under N2. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was neutralized with sat. aq. Na2CO3. The organic phase was collected and the aqueous phase was extracted with DCM (3x). The combined organic phases were washed brine and dried over Na2SO4. The solids were removed by filtration and the filtrate was evaporated to dryness. The crude mixture was purified by flash chromatography on silica gel (0% to 3% MeOH in DCM) to afford 5'-hydroxyspiro[cyclopentane-1,3'-indolin]-2'-one (1.23 g, 60%) as a brown oil.1H-NMR (DMSO-d6, 300 MHz): 1.67-1.71 (m, 2H), 1.86-1.95 (m, 6H), 6.51-6.65 (m, 3H), 8.92 (s, 1H), 9.96 (s, 1H) ppm. LC-MS: C12H13NO2[M+H]+: 204.
With trifluoroacetic acid; bis-[(trifluoroacetoxy)iodo]benzene In chloroform at 20℃; for 12h; 11 Example 11: Compound 11 PIFA (3.31 g, 7.69 mmol) was slowly added to a solution of 11-2 (1.20 g, 6.41 mmol) in trifluoroacetic acid (4.78 mL, 64 mmol) and chloroform (50.00 mL). The reaction was carried out at 20 °C for 12 hours. The reaction mixture was quenched with 5% sodium bicarbonate aqueous solution (200 mL), extracted with ethyl acetate (100 mL× 3). The combined organic phase was washed with saturated saline (100 mL), dried over anhydrous sodium sulfate. After filtration and evaporation, the residue was purified by column chromatography (petroleum ether: ethyl acetate = 2:1) to give the target compound 11-3. 1H NMR (400 MHz, CDCl3) δ 6.79 - 6.55 (m, 3H), 2.24 - 1.72 (m, 8H).
  • 49
  • [ 554457-97-5 ]
  • [ 41058-67-7 ]
  • [ 1434503-05-5 ]
YieldReaction ConditionsOperation in experiment
22% Stage #1: spiro[cyclopentane-1,3'-indol]-2'(1'H)-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: tert-butyl ((2-(chloromethyl)-1-isopentyl-1H-benzo[d]imidazol-5-yl)methyl)carbamate hydrochloride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #3: With hydrogenchloride In 1,4-dioxane at 20℃; for 16h; Inert atmosphere;
  • 50
  • [ 50624-65-2 ]
  • [ 41058-67-7 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 3-(1H-indol-3-yl)propyl bromide With tetrabutyl-ammonium chloride; water; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 25℃; Stage #2: With potassium carbonate In dichloromethane for 2h;
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