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[ CAS No. 6276-03-5 ] {[proInfo.proName]}

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Chemical Structure| 6276-03-5
Chemical Structure| 6276-03-5
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Product Details of [ 6276-03-5 ]

CAS No. :6276-03-5 MDL No. :MFCD00001130
Formula : C14H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HTPXFGUCAUTOEL-UHFFFAOYSA-N
M.W : 210.23 Pubchem ID :80468
Synonyms :

Safety of [ 6276-03-5 ]

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

Application In Synthesis of [ 6276-03-5 ]

* 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 [ 6276-03-5 ]

[ 6276-03-5 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 6276-03-5 ]
  • [ 55341-64-5 ]
YieldReaction ConditionsOperation in experiment
95.5% With thionyl chloride for 2h; Heating;
91% With thionyl chloride for 10h; Heating;
With thionyl chloride
With pyridine; thionyl chloride In diethyl ether
With thionyl chloride for 3h; Heating;
With oxalyl dichloride In dichloromethane for 2h; 4 EXAMPLE 4 To a suspension of 1-fluorenecarboxylic acid (184 mg) and oxalyl chloride (0.2 ml) in dichloromethane (4 ml) was added N,N-dimethylformamide (0.01 ml), and the mixture was stirred for 2 hours.. The resultant solution was evaporated to give a crude acid chloride.. To a suspension of 3-pyridazin-3-yl-phenylamine (150 mg) and pyridine (0.21 ml) in dichloromethane (2 ml) was dropwise added a solution of the acid chloride obtained above in dichloromethane. (5 ml) followed by stirring for an hour.. The mixture was diluted with dichloromethane and washed with an aqueous solution of sodium hydrogen carbonate and brine.. The separated organic layer was dried over sodium sulfate and evaporated under reduced pressure.. The residue was purified by a silica gel column chromatography eluding with 2% methanol in dichloromethane to give N-(3-(pyridazin-3-yl)phenyl)-9H-fluorene-1-carboxamide (44 mg, 13.8%).NMR (DMSO-d6, δ): 4.24 (2H, s). 7.3-7.5(2H, m), 7.5-7.7 (3H, m), 7.7-7.9 (3H, m), 7.99 (1H, dd, J=7.0 Hz, 1.8 Hz), 8.1-8.3 (2H, m), 8.70 (1H, t, J=3.6 Hz), 9.24 (1H, dd, J=4.9 Hz, 1.5 Hz), 10.54 (1H, s) APCI-Mass m/z: 364 (M+1).
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃;
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.5h; Inert atmosphere;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere;

  • 2
  • [ 6276-03-5 ]
  • [ 28314-01-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; methanol
  • 3
  • [ 6276-03-5 ]
  • [ 81699-50-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; ethanol
  • 4
  • [ 1573-92-8 ]
  • [ 6276-03-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; amalgamated zinc; acetic acid
With sodium hydroxide; hydrazine hydrate; trimethyleneglycol at 205℃;
With sodium amalgam; water
With phosphorus; hydrogen iodide; acetic acid
With sodium hydroxide; hydrazine hydrate In diethylene glycol Heating;
With phosphorus; hydrogen iodide; acetic acid In water for 48h; Heating / reflux; 2 A mixture of 9-fluorenone-1-caboxylic acid (6 g, 26.8 mmol), a 55% HI solution HI (10.5 mL) and red phosphorous (9,6 g, 310 mmol) in 400 mL acetic acid was refluxed for 48 h, then concentrated. Following addition of 200 mL of water; the mixture was stirred overnight and filtered. The cake was treated in 200 mL water and 5 mL concentrated NaOH and filtered to remove residual phosphorous. The filtrate was adjusted to pH 2 with 4 N HCl to give a suspension that was filtered, washed with, dried in vacuum to afford 5.47 g of compound 8 as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 4.25 (2H, s), 7.35 (2H, m), 7.55 (1H, t), 7.63 (1H, d), 7.92 (1H, d), 7.96 (1H, d), 8.2 (1H, d).

  • 5
  • [ 6276-03-5 ]
  • [ 917-54-4 ]
  • [ 36272-09-0 ]
YieldReaction ConditionsOperation in experiment
38% In tetrahydrofuran; diethyl ether for 3h; Ambient temperature;
  • 6
  • [ 6276-03-5 ]
  • [ 1730-37-6 ]
YieldReaction ConditionsOperation in experiment
91% With diborane In tetrahydrofuran for 29h; Heating;
Multi-step reaction with 3 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 2: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 3: 3,4-thiene-2,3-diylbis(dicyclohexylphosphine); nickel(II) acetylacetonate dihydrate / 1,4-dioxane; hexane / 16 h / 170 °C / Inert atmosphere; Sealed tube
  • 7
  • [ 6276-03-5 ]
  • 7-iodofluorene-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With potassium permanganate; sulfuric acid; iodine In acetic acid at 100℃; for 4h;
  • 8
  • [ 67-56-1 ]
  • [ 6276-03-5 ]
  • [ 28314-01-4 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid
  • 9
  • [ 6276-03-5 ]
  • [ 13737-38-7 ]
YieldReaction ConditionsOperation in experiment
With bromine Irradiation;
  • 10
  • [ 6276-03-5 ]
  • [ 73728-55-9 ]
YieldReaction ConditionsOperation in experiment
68.5% With acetic acid In tetrahydrofuran; methanol; water 29 1-Fluorenemethanol 1-Fluorenemethanol A solution of 1-fluorenecarboxylic acid (10.0 g, 47.6 mmol) in THF (150 mL) at 0° C. was charged With a 1M solution of BH3 -THF complex in THF (80 mL, 80 mmol). The reaction mixture was stored overnight at room temperature then quenched with 30 mL of 10% AcOH in methanol. After dilution with water (100 mL), the water layer was extracted with ethyl acetate (3*50 mL). The combined organic extracts were washed with 10% potassium carbonate solution, water, brine, dried over magnesium sulfate and evaporated. The residue (white crystals) was washed with ether and dried to afford 1-fluorenemethanol (6.4 g, 68.5%).
59% With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Ambient temperature;
33% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 1h;
With lithium aluminium tetrahydride In diethyl ether Heating;
Multi-step reaction with 2 steps 1: H2SO4 2: LiAlH4
With borane-THF In tetrahydrofuran at 20℃; for 16.5833h; 2 Compound 9 Compound 9 To a slurry of compound 8 (5.47 g, 26 mmol) in 50 mL dry THF, was added dropwise a 1 M solution BH3-THF (28 mL) at room temperature over a 35 minutes period. The mixture was stirred at room temperature for 16 h then quenched by brine. The organic layer was washed with brine, dried over MgSO4, concentrated to give 4.5 g of compound 9 as a yellow solid. 1H NMR (400 MHz, CHCl3) δ 3.9(2H, s), 4.85 (2H, s), 7.35 (4H, m), 7.55 (1H, d), 7.75 (1H, d), 7.8 (1H, d).
In tetrahydrofuran; water 1-Fluorenylmethanol 1-Fluorenylmethanol To a cooled (0°), stirred, solution of 1-fluorenecarboxylic acid (2.10 g, 10.0 mmol) in dry tetrahydrofuran (20 ml) under argon was added lithium aluminium hydride (0.19 g, 5 mmol) added in portions over 10 minutes. After a further 1 hour, water was added cautiously until effervescence ceased. The reaction mixture was partitioned between ethyl acetate and water and filtered. The organic layer was washed with saturated sodium hydrogen carbonate solution followed by water and dried over MgSO4. Evaporation of solvent gave crude product. δH (CDCl3 containing CD3 OD) 3.87 (2H, s), 4.81 (2H, s), 7.2-7.75 (7H, m) ppm

  • 11
  • [ 6276-03-5 ]
  • (4-trifluoromethylsulfanyl-phenoxy)-acetic acid hydrazide [ No CAS ]
  • 9<i>H</i>-fluorene-1-carboxylic acid <i>N</i>'-[(4-trifluoromethylsulfanyl-phenoxy)-acetyl]-hydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In tetrahydrofuran at 20℃; for 40h;
  • 12
  • [ 6276-03-5 ]
  • (4S,7R)-3-[N-(methoxycarbonyl)methyl]-7-amino-9-methoxycarbonyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline [ No CAS ]
  • (4S,7R)-3-[N-(methoxycarbonyl)methyl]-7-[(1-fluorenecarbonyl)amino]-9-methoxycarbonyl-2,3,6,7-tetrahydro-1H,5H-benzo[ij]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 18h;
  • 13
  • [ 6276-03-5 ]
  • 9H-fluorene-1-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 9H-fluorene-1-carboxylic acid With isocyanate de chlorosulfonyle In dichloromethane at 0℃; Stage #2: With triethylamine In dichloromethane at 20℃;
Multi-step reaction with 2 steps 1: thionyl chloride; N,N-dimethyl-formamide / dichloromethane / 12 h / 20 °C / Schlenk technique; Inert atmosphere 2: bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine / toluene / 1 h / 110 °C / Schlenk technique; Inert atmosphere
  • 14
  • [ 656836-79-2 ]
  • [ 6276-03-5 ]
  • C70H47NO11 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 23℃; for 2h;
  • 15
  • [ 6276-03-5 ]
  • [ 252002-18-9 ]
  • C30H32N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 9H-fluorene-1-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In chloroform at 20℃; for 0.0833333h; Stage #2: 3-spiro[2,3-dihydro-1H-indene-1,4'-piperidine]-1-ylpropane-1-amine In chloroform at 20℃; for 0.5h;
  • 16
  • [ 6276-03-5 ]
  • 9<i>H</i>-fluorene-1-carboxylic acid [3-(4-phenyl-piperazin-1-yl)-propyl]-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Heating 2: aq. NaHCO3 / CHCl3 / 1 h / 20 °C / pH 8 - 9
  • 17
  • [ 6276-03-5 ]
  • 9<i>H</i>-fluorene-1-carboxylic acid {3-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-propyl}-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 3 h / Heating 2: aq. NaHCO3 / CHCl3 / 1 h / 20 °C / pH 8 - 9
  • 18
  • [ 6276-03-5 ]
  • [ 95264-32-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 59 percent / LiAlH4 / tetrahydrofuran / 1 h / Ambient temperature 2: 64 percent / pyridinium dichromate, silica gel / CH2Cl2 / 7 h
Multi-step reaction with 2 steps 1: 91 percent / B2H6 / tetrahydrofuran / 29 h / Heating 2: 88 percent / pyridinium chlorochromate on neutral alumina / hexane / 8 h / Ambient temperature
Multi-step reaction with 2 steps 1: SOCl2 2: palladium/charcoal; xylene / Hydrogenation
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C 2: dipyridinium dichromate; silica gel / dichloromethane / 16 h / 20 °C

  • 19
  • [ 6276-03-5 ]
  • [ 36272-09-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / SOCl2 / 10 h / Heating 2: tetrahydrofuran / 1 h / -70 deg C -> room temperature
  • 20
  • [ 6276-03-5 ]
  • syn- and anti-1-acetylfluorene oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 91 percent / SOCl2 / 10 h / Heating 2: tetrahydrofuran / 1 h / -70 deg C -> room temperature 3: NH2OH*HCl, NaOAc / H2O / 2 h / Heating
  • 21
  • [ 6276-03-5 ]
  • [ 110827-02-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 91 percent / B2H6 / tetrahydrofuran / 29 h / Heating 2: 88 percent / pyridinium chlorochromate on neutral alumina / hexane / 8 h / Ambient temperature 3: ZnI2 / CH2Cl2 / 1 h / Ambient temperature
  • 22
  • [ 6276-03-5 ]
  • [ 110827-06-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 91 percent / SOCl2 / 10 h / Heating 2: tetrahydrofuran / 1 h / -70 deg C -> room temperature 3: NH2OH*HCl, NaOAc / H2O / 2 h / Heating 4: 95 percent / H2, conc. HCl / Pd/C / methanol / 21 h / 2280 Torr / Ambient temperature
  • 23
  • [ 6276-03-5 ]
  • [ 110826-98-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 91 percent / B2H6 / tetrahydrofuran / 29 h / Heating 2: 88 percent / pyridinium chlorochromate on neutral alumina / hexane / 8 h / Ambient temperature 3: ZnI2 / CH2Cl2 / 1 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 3 h
  • 24
  • [ 6276-03-5 ]
  • [ 53221-20-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 38 percent / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature 2: CuBr2 / ethyl acetate; CHCl3 / 3.5 h / Heating
  • 25
  • [ 6276-03-5 ]
  • [ 98216-67-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 38 percent / tetrahydrofuran; diethyl ether / 3 h / Ambient temperature 2: CuBr2 / ethyl acetate; CHCl3 / 3.5 h / Heating 3: dimethylformamide / Ambient temperature
  • 26
  • [ 206-44-0 ]
  • [ 6276-03-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: CrO3; acetic acid 2: sodium hydroxide; trimethylene glycol; aqueous hydrazine hydrate / 205 °C
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; aqueous acetic acid 2: sodium hydroxide; trimethylene glycol; aqueous hydrazine hydrate / 205 °C
Multi-step reaction with 2 steps 1: chromium (VI)-oxide; aqueous acetic acid 2: amalgamated zinc; aqueous hydrochloric acid; acetic acid
  • 27
  • [ 6276-03-5 ]
  • [ 88909-93-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen chloride; methanol 2: ethanol; aqueous hydrazine hydrate 3: aqueous hydrochloric acid; acetic acid; aqueous sodium nitrite solution
Multi-step reaction with 2 steps 1: SOCl2 2: NaN3
  • 28
  • [ 6276-03-5 ]
  • [ 107413-01-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: H2SO4 2: LiAlH4 3: PBr3
  • 29
  • [ 6276-03-5 ]
  • [ 100715-85-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: H2SO4 2: LiAlH4 3: PBr3 4: H2S, NaOEt / ethanol
  • 30
  • [ 333793-36-5 ]
  • [ 6276-03-5 ]
  • [ 333793-49-0 ]
YieldReaction ConditionsOperation in experiment
64.7% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; 28 EXAMPLE 28 To a suspension of 9H-fluorene-1-carboxylic acid (106 mg) and 3-(4,5-dimethylimidazol-1-yl)aniline (94 mg) in dichloromethane (2 ml) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (135 mg) and 4-dimethylaminopyridine (31 mg), and the mixture was stirred for 24 hours.. The mixture was diluted with dichloromethane and washed with water and brine.. The mixture was dried over magnesium sulfate and evaporated under reduced pressure.. The residue was triturated with methanol, and the insoluble material was collected by filtration and dried to give N-[3-(4,5-dimethylimidazol-1-yl)-phenyl]-9H-fluorene-1-carboxamide (123 mg, 64.7%). APCI-mass m/z: 380 (M+1) NMR (DMSO-d6, δ); 2.13 (6H, s), 4.20 (2H, s), 7.15 (1H, d, J=8.4 Hz), 7.3-7.5 (6H, m), 7.75 (1H, d, J=6.9 Hz), 7.8-7.9 (2H, m), 7.98 (1H, d, J=6.6 Hz), 8.13 (1H, d, J=6.9 Hz), 10.57 (1H, s):
  • 31
  • [ 138830-48-5 ]
  • [ 6276-03-5 ]
  • [ 333793-47-8 ]
YieldReaction ConditionsOperation in experiment
29.2% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h; 27 EXAMPLE 27 To a suspension of 9H-fluorene-1-carboxylic acid (79 mg) and 3-(4-methylimidazol-1-yl)aniline (65 mg) in dichloromethane (2 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (101 mg) and 4-dimethylaminopyridine (23 mg), and the mire was stirred for 24 hours.. The mix e was diluted with dichloromethane, washed with water and brine.. The mixture was dried over magnesium sulfate and evaporated under reduced pressure.. The residue was triturated with methanol, and the insoluble material was collected by filtration and dried to give N-[3-(4-methylimidazol-1-yl)-phenyl]-9H-fluorene-1-carboxamide (40 mg, 29.2%). APCI-mass m/z: 366 (M+1) NMR (DMSO-d6 δ; 2.18 (3H, s), 4.21 (2H, s), 7.3-7.8 (9H, m), 7.98 (1H, d, J=6.5 Hz), 8.0-8.1 (2H, m), 8.13 (1H, d, J=7.3 Hz), 10.53 (1H, s).
  • 32
  • [ 107-10-8 ]
  • [ 79-37-8 ]
  • [ 1476-11-5 ]
  • [ 6276-03-5 ]
  • [ 182428-28-0 ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide (Z)-9-[4-[4-(2,3-Dihydro-1-oxo-1H-isoindol-2-yl)-1-piperidinyl]-2-butenyl]-N-propyl-9H-fluorene-9-carboxamide, monohydrochloride STR227 (Z)-9-[4-[4-(2,3-Dihydro-1-oxo-1H-isoindol-2-yl)-1-piperidinyl]-2-butenyl]-N-propyl-9H-fluorene-9-carboxamide, monohydrochloride STR227 Butyllithium (8.4 mL, 2.5M in hexane, 21 mmol) was added dropwise over 10 min to a solution of fluorenecarboxylic acid (Aldrich Chemical Co.) (2.10 g, 10 mmol) in THF (50 mL) at 0° C. under argon. During addition of the first equivalent of BuLi, the reaction became thick with a white precipitate which became yellow and cleared after addition of the second equivalent. The reaction was stirred at 0° C. for 20 min, then cis-1,4-dichloro-2-butene (1.2 mL, 11 mmol) was added dropwise over 5 min. The reaction lightened in color during addition and was stirred at 0° C. for 3 h, then poured into 1N HCl (50 mL) and extracted with CH2 Cl2 (3*50 mL). The combined organic layers were washed with brine (30 mL) then dried over MgSO4. Evaporation provided 3.5 g of a yellow oil containing crystalline solid. The crude residue was triturated with hexane (20 mL). The supernatant was decanted, and the residue pumped under high vacuum to give 2.93 g of a tan solid. To a suspension of the crude acid prepared above (1.42 g, 4.77 mmol) and N,N-dimethylformamide (5 drops) in CH2 Cl2 (15 mL) at RT under argon was added oxalyl chloride (3.6 mL, 2.0M in CH2 Cl2, 7.16 mmol). The reaction bubbled for 10 min, then the reaction was stirred at RT for 1.5 h, at which time all solids had dissolved. The reaction was concentrated in vacuo to give an orange oil. The crude acid chloride was dissolved in CH2 Cl2 (15 mL) and cooled to 0° C. Propylamine (1.2 mL, 14.3 mmol) was added dropwise over 1 min, and the reaction was stirred at 0° C. for 10 min. The reaction was partitioned between EtOAc (50 mL) and water (20 mL). The organic layer was washed with 1N HCl (2*20 mL) and brine (20 mL), then dried over MgSO4. Evaporation gave 1.7 g of an orange oil, which was purified by flash chromatography on silica gel (150 g) eluding with CH2 Cl2 to give title compound (1.38 g, 84%) as a pale yellow oil.
  • 33
  • [ 6276-03-5 ]
  • [ 52651-79-3 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; H2; ammonia; lithium In ethanol; water; acetic acid 12.A A. A. 1,2,3,4,4a,9a-Hexahydrofluorene-1-carboxylic acid A solution of 21.0 g (0.10 mole) of fluorene-1-carboxylic acid in 25 ml of absolute ethanol is added to 500 ml of liquid ammonia and the solution treated portionwise with 4.2 g (0.60 mole) of lithium cut in small pieces. After evaporation of the NH3, the residue is cooled in ice and treated first with water and then with sufficient conc. HCl to render it strongly acidic. The crude partially reduced product is filtered off and dissolved in acetic acid. Reduction of the solution over 1 g of PtO2 under up to 55 psi of H2 is complete after about 1 equivalent of H2 is taken up. The solution is freed of catalyst and taken to dryness. Recrystallization from hexane affords the desired product, mp 138°-139°.
  • 34
  • [ 872602-75-0 ]
  • [ 6276-03-5 ]
  • [ 55341-64-5 ]
  • 5-[(9H-fluorene-1-carbonyl)-amino]-nicotinic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In oxalyl dichloride; dichloromethane 171 Preparation 171 Preparation 171 To a solution of 9H-fluorene-1-carboxylic acid (0.49g) in dichloromethane (2ml) were added in turn oxalyl chloride (0.4ml) and a catalytic amount of N,N-dimethylformamide (2drops) at ambient temperature. After stirring at ambient temperature for 1 hour, the reaction mixture was evaporated in vacuo, and the residue was added in dichloromethane (5ml) to give a solution of 9H-fluorene-1-carboxyl chloride. To a solution of 5-amino-methyl nicotinic acid (0.53g) in dichloromethane (5ml) were added pyridine (1.0ml) and the acid chloride solution at 0°C. After stirring at 0°C for 1 hour, the reaction mixture was diluted with dichloromethane, washed with aqueous potassium carbonate (10%) and brine, and dried over potassium carbonate. Evaporation gave a residue which was triturated with diisopropyl ether to give 5-[(9H-fluorene-1-carbonyl)-amino]-nicotinic acid methyl ester (0.492g).
  • 35
  • 3-methyl-N2-(2-pyridylmethyl)-2,5-pyridyldiamine [ No CAS ]
  • added1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [ No CAS ]
  • [ 6276-03-5 ]
  • N-[5-methyl-6-[methyl(pyridin-2-ylmethyl)amino]-pyridin-3-yl]-9H-fluorene-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dmap In dichloromethane 175 Example 175 Example 175 To a suspension of 9H-fluorene-1-carboxylic acid (835mg) and 3-methyl-N2-(2-pyridylmethyl)-2,5-pyridyldiamine (845mg) in dichloromethane (30ml) was added1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.14g) and 4-dimethylaminopyridine (242mg) and stirred for 18 hours. The mixture was diluted with dichloromethane, washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 150g, eluding with 1-4% methanol/dichloromethane) to give N-[5-methyl-6-[methyl(2-pyridylmethyl)amino]-3-pyridyl]-9H-fluorene-1-carboxamide (1.14g).
  • 36
  • [ 79-37-8 ]
  • [ 6276-03-5 ]
  • [ 55341-64-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; N,N-dimethyl-formamide 91 Example 91 Example 91 To a suspension of 9H-fluorene-1-carboxylic acid (147mg) in dichloromethane (3ml) was added oxalyl chloride (0.2ml) and N,N-dimethylformamide (0.01ml). The mixture was stirred for 2 hours and evaporated to give crude 9H-fluorene-1-carboxylic acid chloride.
  • 37
  • C34H36N3O3Pol [ No CAS ]
  • [ 6276-03-5 ]
  • [ 403987-28-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 9H-fluorene-1-carboxylic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In 1-methyl-pyrrolidin-2-one; dichloromethane for 0.5h; Stage #2: C34H36N3O3Pol With N-ethyl-N,N-diisopropylamine In 1-methyl-pyrrolidin-2-one; dichloromethane at 20℃; for 24h; Stage #3: With chlorotriisopropylsilane; trifluoroacetic acid In dichloromethane at 20℃; for 1h; B.5 EXAMPLE B.5 [0218] Fluorene-4-carboxylic acid (0.00023 mole) in 1 ml of 1/1 mixture of DCM/NMP was added to PyBOP (0.00046 mole) in DCM (1 ml). This mixture was stood for 30 minutes, then added to the resin of example A.30. DCM (5 ml) was added, followed by DIPEA (0.00057 mole). The reaction mixture was shaken for 24 hours at room temperature, then filtered, washed three times with DCM, three times with first methanol, followed by secondly DCM. A mixture of TFA/DCM/TIS (4 ml; 75/23/2) was added and the mixture was shaken for one hour at room temperature. The mixture was filtered, the filter residue was washed with 2 ml of a mixture of TFA/DCM/TIS (75/23/2) and with DCM (2 ml). The filtrate was blown dry at 50 C. under a gentle stream of nitrogen. The residue was dissolved in DCM (5 ml), then blown dry once more. This fraction was purified by high performance liquid chromatography over Hyperprep RP-C18 BDS (100 g, 100 Å, 8 μm; eluent: [(0.5% NH4OAc in H2O)/CH3CN 90/10)]/CH3OH/CH3CN (0 minute) 75/25/0, (10 minutes) 0/50/50, (16 minutes) 0/0/100, (18.10-20.00 minutes) 75/25/0). The pure fractions were collected and the organic solvent was evaporated. The aqueous concentrate was extracted with DCM/aqueous potassium carbonate solution, then separated over Extrelut. The organic phase was blown dry under nitrogen at 50 C. The residue was dried further under vacuum at 60 C., yielding 0.0046 g of the compound identified as No. 29 in the following table F-1. Compounds identified as No. 30 to No. 36 in the following table F-1 were similarly prepared while using the same experimental procedure and replacing fluorene-4-carboxylic acid by the appropriate reactive acid.
  • 38
  • [ 86-73-7 ]
  • [ 124-38-9 ]
  • [ 6276-03-5 ]
YieldReaction ConditionsOperation in experiment
99% With Et3SiB(C6F5)4 In chlorobenzene at 20℃; for 18h;
  • 39
  • [ 6276-03-5 ]
  • [ 50-01-1 ]
  • N-(9H-fluorene-1-carbonyl)guanidine monohydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% Stage #1: 9H-fluorene-1-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20 - 50℃; for 1h; Stage #2: guanidine hydrochloride With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h; Cooling with ice; 5.1.1 N-(Diaminomethylene)-9H-fluorene-2-carboxamide (4) To a solution of 9H-fluorene-2-carboxylic acid (15, 520mg, 2.47mmol) in DMF (6mL) was added 1,1′-carbonyldiimidazole (CDI) (440mg, 2.71mmol) at room temperature, the reaction mixture was stirred at 50°C for 1h, then allowed to cool. This mixture was added under ice-cooling to a solution which had been prepared by addition of NaH (55% dispersion in mineral oil; 500mg, 12.5mmol) to DMF (6mL) solution of guanidine hydrochloride (1.18g, 12.3mmol) and stirring at room temperature for 1h, and the reaction mixture was stirred at room temperature for 2h. The reaction mixture was concentrated in vacuo and added CHCl3 and water. The aqueous layer was extracted with CHCl3, and the combined organic layer was washed with 1M NaOH aq, dried over MgSO4. After evaporation in vacuo, the resultant residue was purified by silica gel column chromatography (EtOAc), recrystalization from MeOH to give the title compound 4 (140mg, 23%) as a pale yellow solid.
  • 40
  • [ 6276-03-5 ]
  • phenyl 9H-fluorene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1.5 h / 20 °C / Inert atmosphere 2: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
  • 41
  • [ 6276-03-5 ]
  • [ 93-55-0 ]
  • C23H18O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 2,2,6,6-tetramethyl-piperidine-N-oxyl; chloro(1,5-cyclooctadiene)rhodium(I) dimer; copper diacetate; cesium fluoride In toluene at 120℃; for 24h; Inert atmosphere;
  • 42
  • [ 6276-03-5 ]
  • 9H-Fluorene-1-carbonyl Fluoride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 9H-fluorene-1-carboxylic acid In dichloromethane at 0℃; for 0.5h; Schlenk technique; Stage #2: With (bis-(2-methoxyethyl)amino)sulfur trufluoride In dichloromethane at 0℃; for 0.5h; Schlenk technique; 3.2.2. Representative Procedure for the Synthesis of Acyl Fluorides from Carboxylic Acids General procedure: To a 20 mL of Schlenk tube charged with a magnetic stir bar, were successively added carboxylic acid (3.0 mmol) and CH2Cl2 (15 mL). After the mixture was stirred at 0 °C for 30 min, Deoxo-Fluorreagent (608 L, 3.3 mmol, 1.1 equiv) was slowly added to the reaction mixture. After the reaction mixture was stirred at 0 °C for 30 min, the solution was slowly poured into saturated NaHCO3,extracted with CH2Cl2 (3 15 mL), and dried over MgSO4. The crude product was purified by flash chromatography on silica gel to aord the corresponding acyl fluorides 1 [36].
  • 43
  • [ 384-64-5 ]
  • [ 6276-03-5 ]
  • 1-(9H-fluoren-1-yl)-4,4-difluoro-3-phenylbut-3-en-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium hydrogencarbonate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 48h; Molecular sieve; Inert atmosphere; Sealed tube; Irradiation;
  • 44
  • [ 928-49-4 ]
  • [ 6276-03-5 ]
  • 3,4-diethylindeno[1,2-h]isochromen-1(11H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
15% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate dihydrate In o-xylene at 150℃; for 6h; Inert atmosphere;
  • 45
  • [ 673-32-5 ]
  • [ 6276-03-5 ]
  • 1,4-dimethyl-2,3-diphenyl-11H-benzo[a]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With copper(II) acetate dihydrate; [(Rh(η-C5H5)I2)n] In o-xylene at 150℃; for 6h; Inert atmosphere;
  • 46
  • [ 6276-03-5 ]
  • [ 501-65-5 ]
  • 3,4-diphenylindeno[1,2-h]isochromen-1(11H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper(II) acetate dihydrate In o-xylene at 150℃; for 6h; Inert atmosphere;
  • 47
  • [ 6276-03-5 ]
  • [ 501-65-5 ]
  • 1,2,3,4-tetraphenyl-11H-benzo[a]fluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With copper(II) acetate dihydrate; [(Rh(η-C5H5)I2)n] In o-xylene at 150℃; for 6h; Inert atmosphere;
  • 48
  • [ 6276-03-5 ]
  • (6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methanamine trifluoroacetate [ No CAS ]
  • N-((6-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-9H-fluorene-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h; Inert atmosphere;
  • 49
  • [ 6276-03-5 ]
  • 8-(9H-fluoren-1-yl)-4-methyl-2,6-dioxohexahydro[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium 8-uide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis(1,5-cyclooctadiene)nickel (0); bis(dicyclohexylphosphino)methane / toluene / 24 h / 150 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: toluene; N,N-dimethyl-formamide / 4 h / 90 °C / Inert atmosphere; Schlenk technique; Sealed tube
  • 50
  • [ 13826-27-2 ]
  • [ 6276-03-5 ]
  • C19H13BO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis(1,5-cyclooctadiene)nickel (0); bis(dicyclohexylphosphino)methane In toluene at 150℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube;
Same Skeleton Products
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