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[ CAS No. 5411-61-0 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 5411-61-0
Chemical Structure| 5411-61-0
Chemical Structure| 5411-61-0
Structure of 5411-61-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 5411-61-0 ]

CAS No. :5411-61-0 MDL No. :MFCD10565602
Formula : C10H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :OJDMKCLDADYDRL-UHFFFAOYSA-N
M.W : 241.08 Pubchem ID :223379
Synonyms :

Calculated chemistry of [ 5411-61-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.68
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 2.33
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 2.05
Log Po/w (SILICOS-IT) : 3.39
Consensus Log Po/w : 2.49

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.08
Solubility : 0.201 mg/ml ; 0.000835 mol/l
Class : Soluble
Log S (Ali) : -2.52
Solubility : 0.726 mg/ml ; 0.00301 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.1
Solubility : 0.0191 mg/ml ; 0.0000791 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.2

Safety of [ 5411-61-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5411-61-0 ]

* 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 [ 5411-61-0 ]

[ 5411-61-0 ] Synthesis Path-Downstream   1~53

  • 1
  • [ 66192-02-7 ]
  • [ 5411-61-0 ]
YieldReaction ConditionsOperation in experiment
86% With polyphosphoric acid at 60℃; for 1h; Inert atmosphere;
66% With PPA at 60℃; for 1h;
62% With polyphosphoric acid at 60℃; for 1h; 7-methoxyindan-1-one (4) [23]. The mixture of polyphosphoric acid (12 g) was heated to 60 °C and 3-(2-bromo-5-methoxyphenyl)propanoic acid (4.06 mmol, 1.05 g) was added in small portions. The mixture was stirred at 60 °C for 1 h. Ice was then added to the mixture and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The collected organic layers were washed with H2O (2 × 5 ml), 5% NaHCO3 (2 × 5 mL), brine (2 × 5 ml) and then dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography with CHCl3/MeOH (95:5) as eluent to afford 4-bromo-7-methoxyindan-1-one as an orange solid (0.60 g, 62% yield); GC-MS m/z 242 (M+ + 2, 54), 240 (M+, 55), 213 (95), 211 (100). A solution of compound 4-bromo-7-methoxyindan-1-one (2.50 mmol, 0.60 g) in EtOH, NaOAc (3.00 mmol, 0.25 g) was added. The mixture was hydrogenated at 4 atm in the presence of Pd on activated carbon 10% overnight. The reaction mixture was then filtered on a Celite pad and the filtrate evaporated to dryness.
With hydrogen fluoride
With PPA
With PPA 34 Example 34, Preparation of 4-Bromo-7-methoxy-2,3-dihydro-1H-inden-1-one Example 34 Preparation of 4-Bromo-7-methoxy-2,3-dihydro-1H-inden-1-one polyphosphoric acid (600 g) was heated to 90° C and 30 g 2-bromo-5-methoxyphenyl propionic acid was added over 25 min. The reaction was stirred an additional 10 min and then quenched by addition to 2 kg ice. The reaction mixture was extracted with methylene chloride, and the organic extracts were washed with 5% NaHCO3 brine, dried (MgSO4, and evaporated. The product was recrystallized from methanol to yield 15.10 g of a light yellow solid, mp: 125-8° C. NMR (CDCl3 δ 2.70 (m, 2H), 3.00 (m, 2H), 3.95 (s, 3H), 6.73 (d, 1H), 7.66 (d, 1H).
With PPA 34 Preparation of 4-Bromo-7-methoxy-2,3-dihydro-1H-inden-1-one EXAMPLE 34 Preparation of 4-Bromo-7-methoxy-2,3-dihydro-1H-inden-1-one Polyphosphoric acid (600 g) was heated to 90° C. and 30 g 2-bromo-5-methoxyphenyl propionic acid was added over 25 min. The reaction was stirred an additional 10 min and then quenched by addition to 2 kg ice. The reaction mixture was extracted with methylene chloride, and the organic extracts were washed with 5% NaHCO3, brine, dried (MgSO4), and evaporated. The product was recrystallized from methanol to yield 15.10 g of a light yellow solid, mp: 125-8° C. NMR (CDCl3) δ 2.70 (m, 2H), 3.00 (m, 2H), 3.95 (s, 3H), 6.73 (d, 1H), 7.66 (d, 1H).

  • 2
  • [ 5411-61-0 ]
  • [ 34985-41-6 ]
YieldReaction ConditionsOperation in experiment
35% With palladium 10% on activated carbon; hydrogen; sodium acetate; In ethanol; under 3040.2 Torr; The mixture of polyphosphoric acid (12 g) was heated to 60 C and 3-(2-bromo-5-methoxyphenyl)propanoic acid (4.06 mmol, 1.05 g) was added in small portions. The mixture was stirred at 60 C for 1 h. Ice was then added to the mixture and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The collected organic layers were washed with H2O (2 × 5 ml), 5% NaHCO3 (2 × 5 mL), brine (2 × 5 ml) and then dried over Na2SO4 and concentrated under reduced pressure. The crude residue was purified by column chromatography with CHCl3/MeOH (95:5) as eluent to afford 4-bromo-7-methoxyindan-1-one as an orange solid (0.60 g, 62% yield); GC-MS m/z 242 (M+ + 2, 54), 240 (M+, 55), 213 (95), 211 (100). A solution of compound 4-bromo-7-methoxyindan-1-one (2.50 mmol, 0.60 g) in EtOH, NaOAc (3.00 mmol, 0.25 g) was added. The mixture was hydrogenated at 4 atm in the presence of Pd on activated carbon 10% overnight. The reaction mixture was then filtered on a Celite pad and the filtrate evaporated to dryness. The crude was purified by column chromatography with CH2Cl2 as eluent to obtain an orange oil (0.14 g, 35%); 1H-NMR 2.60-2.70 (m, 2H, ArCH2), 3.05-309 (m, 2H, CH2CO), 3.79 (s, 3H, OCH3), 6.77 (d, 1H, J = 8.25 Hz, aromatic), 7.00 (d, 1H, J = 7.7, aromatic), 7.51 (t, 1H, J = 8.2 Hz, aromatic); GC-MS m/z 162 (M+, 32), 121 (100), 91 (12).
  • 3
  • [ 10516-71-9 ]
  • [ 5411-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / bromine / CH2Cl2 / 0.25 h / 0 °C 2: 66 percent / polyphosphoric acid / 1 h / 60 °C
Multi-step reaction with 2 steps 1: tetrachloromethane; bromine / -10 °C 2: liquid hydrogen fluoride
Multi-step reaction with 2 steps 1: bromine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 2: polyphosphoric acid / 1 h / 60 °C / Inert atmosphere
  • 4
  • [ 5411-61-0 ]
  • [ 138967-86-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C
  • 5
  • [ 5411-61-0 ]
  • 1-Ethoxycarbonylmethyl-7-methoxy-indan-2-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h
  • 6
  • [ 5411-61-0 ]
  • cis-ethyl 2-(diethoxymethyl)-7-methoxyindan-1-acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr
  • 7
  • [ 5411-61-0 ]
  • (1R,2S)-7-Methoxy-1-propylcarbamoylmethyl-indan-2-carboxylic acid propylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h
  • 8
  • [ 5411-61-0 ]
  • (1R,2S)-1-(Benzylcarbamoyl-methyl)-7-methoxy-indan-2-carboxylic acid benzylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h
  • 9
  • [ 5411-61-0 ]
  • cis-1-(2-hydroxyethyl)-2-(hydroxymethyl)-7-methoxyindan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 94 percent / 96 percent H2SO4, m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 5: 76 percent / LiAlH4 / tetrahydrofuran / 2 h
  • 10
  • [ 5411-61-0 ]
  • trans-1-(2-hydroxyethyl)-2-(hydroxymethyl)-7-methoxyindan [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 81 percent / LiAlH4 / tetrahydrofuran / 2 h
  • 11
  • [ 5411-61-0 ]
  • cis-5-methoxy-2-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene / 48 h / Heating 9: BH3*THF / tetrahydrofuran / 4 h / Heating
  • 12
  • [ 5411-61-0 ]
  • trans-5-methoxy-2-propyl-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene / 48 h / Heating 9: BH3*THF / tetrahydrofuran / 4 h / Heating
  • 13
  • [ 5411-61-0 ]
  • cis-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene; H2O / 72 h / Heating 9: 47 percent / LiAlH4 / tetrahydrofuran / 3 h / 25 °C
Multi-step reaction with 7 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 94 percent / 96 percent H2SO4, m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 5: 76 percent / LiAlH4 / tetrahydrofuran / 2 h 6: triethylamine / CH2Cl2 / 1 h / 0 °C 7: 82 percent / 2 h / 75 °C
  • 14
  • [ 5411-61-0 ]
  • trans-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 81 percent / LiAlH4 / tetrahydrofuran / 2 h 8: triethylamine / CH2Cl2 / 1 h / 0 °C 9: 84 percent / 2 h / 75 °C
Multi-step reaction with 9 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene; H2O / 72 h / Heating 9: 0.81 g / LiAlH4 / tetrahydrofuran / 3 h / 25 °C
  • 15
  • [ 5411-61-0 ]
  • cis-2-propyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene / 48 h / Heating
  • 16
  • [ 5411-61-0 ]
  • trans-2-propyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene / 48 h / Heating
  • 17
  • [ 5411-61-0 ]
  • cis-ethyl 2-carboethoxy-7-methoxyindan-1-acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 94 percent / 96 percent H2SO4, m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C
  • 18
  • [ 5411-61-0 ]
  • trans-ethyl 2-carboethoxy-7-methoxyindan-1-acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating
  • 19
  • [ 5411-61-0 ]
  • cis-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene; H2O / 72 h / Heating
  • 20
  • [ 5411-61-0 ]
  • trans-2-benzyl-5-methoxy-2,3,4,4a,9,9a-hexahydro-1H-indeno<2,1-c>pyridine-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 1.) trimethylaluminium / 1.) toluene, 1 h, 2.) toluene, reflux, 2.5 h 8: p-TsOH / xylene; H2O / 72 h / Heating
  • 21
  • [ 5411-61-0 ]
  • trans-1-(2-hydroxyethyl)-2-(hydroxymethyl)-7-methoxyindanbismesylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 6.0 M aq. HCl / tetrahydrofuran / 2.5 h / 25 °C 5: aq. AgNO3, aq. KOH / ethanol / 0.5 h 6: 96 percent H2SO4 / 2 h / Heating 7: 81 percent / LiAlH4 / tetrahydrofuran / 2 h 8: triethylamine / CH2Cl2 / 1 h / 0 °C
  • 22
  • [ 5411-61-0 ]
  • cis-1-(2-hydroxyethyl)-2-(hydroxymethyl)-7-methoxyindanbismesylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1.) BF3*Et2O, 2.) ethyldiisopropylamine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, -78 to -15 deg C, 2 h 2: 1.) LiHMDS / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 2.5 h 3: 91 percent / NaOAc*3H2O, H2 / 10 percent Pd/C / ethanol / 3040 Torr 4: 94 percent / 96 percent H2SO4, m-chloroperbenzoic acid / CH2Cl2 / 1 h / 0 °C 5: 76 percent / LiAlH4 / tetrahydrofuran / 2 h 6: triethylamine / CH2Cl2 / 1 h / 0 °C
  • 23
  • [ 125714-92-3 ]
  • [ 5411-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1) NaOEt / 1) EtOH 2) CCl4, reflux, 2 h 2: 96 percent / 5percent aq.NaOH / 4 h / 80 °C 3: 97 percent / 180 °C 4: 14 percent / Polyphosphorsaeure / 12 h / 80 °C 5: 1) LDA / 1) THF, hexane, 10 min 2) r.t., 12 h
Multi-step reaction with 5 steps 1: 1) NaOEt / 1) EtOH 2) CCl4, reflux, 2 h 2: 96 percent / 5percent aq.NaOH / 4 h / 80 °C 3: 97 percent / 180 °C 4: 14 percent / Polyphosphorsaeure / 12 h / 80 °C
Multi-step reaction with 5 steps 1: 1) NaOEt / 1) EtOH 2) CCl4, reflux, 12 h 2: 96 percent / 5percent aq.NaOH / 4 h / 80 °C 3: 97 percent / 180 °C 4: 14 percent / Polyphosphorsaeure / 12 h / 80 °C 5: 1) LDA / 1) THF, hexane, 10 min 2) r.t., 12 h
Multi-step reaction with 5 steps 1: 1) NaOEt / 1) EtOH 2) CCl4, reflux, 12 h 2: 96 percent / 5percent aq.NaOH / 4 h / 80 °C 3: 97 percent / 180 °C 4: 14 percent / Polyphosphorsaeure / 12 h / 80 °C

  • 25
  • BF3.Et2 O [ No CAS ]
  • [ 5411-61-0 ]
  • [ 7087-68-5 ]
  • [ 122-51-0 ]
  • [ 131818-60-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; sodium hydrogencarbonate 35 Preparation of 4-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethyl acetal EXAMPLE 35 Preparation of 4-Bromo-7-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxaldehyde diethyl acetal Triethyl orthoformate (16.5 ml) was cooled to -30° C. and 15.0 ml BF3.Et2 O in 50 ml methylene chloride was added. The reaction was warmed to 0° C. for 15 min, and then cooled to -78° C. To the reaction was added 12.05 g of the product from Example 34 in 50 ml methylene chloride, followed by dropwise addition of 19.4 ml diisopropyl ethyl amine. The reaction was then warmed to -15° C. for 2 h, then quenched in 5% NaHCO3 solution and extracted with methylene chloride. The organic extracts were washed with brine, dried (MgSO4), and the solvent removed. The crude product was triturated with cold hexane, and the crystalline product collected to yield 14.60 g of a white solid, mp: 76-8° C. NMR (CDCl3) δ 1.05 (t, 3H), 1.27 (t, 3H), 3.03 (m, 2H), 3.30 (m, 1H), 3.43-3.80 (m, 4H), 3.95 (s, 3H), 5.00 (d, 1H), 6.71 (d, 1H), 7.63 (d, 1H).
  • 26
  • [ 5411-61-0 ]
  • [ 928169-32-8 ]
YieldReaction ConditionsOperation in experiment
98% With sodium tetrahydroborate In methanol at 0℃; for 2h;
  • 27
  • [ 5411-61-0 ]
  • [ 74-88-4 ]
  • [ 881190-30-3 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 4-bromo-7-methoxyindan-1-one With sodium hydride In 1,2-dimethoxyethane for 0.166667h; Stage #2: iodomethane In 1,2-dimethoxyethane at 0 - 20℃; Further stages.;
67% Stage #1: 4-bromo-7-methoxyindan-1-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: iodomethane In tetrahydrofuran; mineral oil at 0 - 23℃; for 21h; Inert atmosphere; Schlenk technique;
  • 28
  • [ 5411-61-0 ]
  • [ 74904-29-3 ]
  • 29
  • [ 6099-04-3 ]
  • [ 5411-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen; palladium on activated charcoal / ethanol / 12 h / 50 °C / 52505.3 Torr 2: bromine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 3: polyphosphoric acid / 1 h / 60 °C / Inert atmosphere
  • 30
  • [ 591-31-1 ]
  • [ 5411-61-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine; piperidine / 9 h / Inert atmosphere; Reflux 2: hydrogen; palladium on activated charcoal / ethanol / 12 h / 50 °C / 52505.3 Torr 3: bromine / dichloromethane / 0.25 h / 20 °C / Inert atmosphere 4: polyphosphoric acid / 1 h / 60 °C / Inert atmosphere
  • 31
  • [ 2398-37-0 ]
  • [ 5411-61-0 ]
  • 7-bromo-4-methoxy-3-(3-methoxyphenyl)-1H-indene [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 3-methoxyphenyl bromide With magnesium In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #2: 4-bromo-7-methoxy-2,3-dihydro-1H-inden-1-one In tetrahydrofuran at 20℃; for 42h; Inert atmosphere; Stage #3: With toluene-4-sulfonic acid In toluene for 3h; Inert atmosphere; Dean-Stark; Reflux;
  • 32
  • [ 5411-61-0 ]
  • methyl (1R,2S)-4-bromo-2-((tert-butoxycarbonyl)amino)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere
  • 33
  • [ 5411-61-0 ]
  • (1R,2S)-methyl 2-(tert-butoxycarbonylamino)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C
  • 34
  • [ 5411-61-0 ]
  • (1R,2S)-methyl 2-amino-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydro-1H-indene-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere
  • 35
  • [ 5411-61-0 ]
  • N-((1R,2S)-1-(hydroxymethyl)-7-methoxy-1-(3-methoxyphenyl)-2,3-dihydro-1Hinden-2-yl)-2-(2-iodo-5-methoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 36
  • [ 5411-61-0 ]
  • (4aS,9aS)-3-(2-iodo-5-methoxyphenyl)-5-methoxy-4a-(3-methoxyphenyl)-1,4a,9,9atetrahydro-2H-indeno[2,1-b]pyridin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere
  • 37
  • [ 5411-61-0 ]
  • tert-butyl (4aS,9aS)-3-(2-iodo-5-methoxyphenyl)-5-methoxy-4a-(3-methoxyphenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 38
  • [ 5411-61-0 ]
  • tert-butyl (4aS,9aS)-3-(4'-(benzoyloxy)-4'-(2-(benzoyloxy)ethyl)-4-methoxy-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-yl)-5-methoxy-4a-(3-methoxyphenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere
  • 39
  • [ 5411-61-0 ]
  • tert-butyl (4aS,9aS)-3-(4'-hydroxy-4'-(2-hydroxyethyl)-4-methoxy-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-yl)-5-methoxy-4a-(3-methoxyphenyl)-2,4a,9,9atetrahydro-1H-indeno[2,1-b]pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 18 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere
  • 40
  • [ 5411-61-0 ]
  • tert-butyl (4aS,9aS)-3-(4'-hydroxy-4-methoxy-4'-(2-((methylsulfonyl)oxy)ethyl)-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-yl)-5-methoxy-4a-(3-methoxyphenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 19 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere 19.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere
  • 41
  • [ 5411-61-0 ]
  • tert-butyl (4aS,9aS)-3-(4'-hydroxy-4'-(2-iodoethyl)-4-methoxy-2',3',4',5'-tetrahydro-[1,1'-biphenyl]-2-yl)-5-methoxy-4a-(3-methoxyphenyl)-2,4a,9,9a-tetrahydro-1H-indeno[2,1-b]pyridine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 20 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere 19.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 20.1: lithium iodide / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere
  • 42
  • [ 5411-61-0 ]
  • (11aS,16bS)-2,16-dimethoxy-16b-(3-methoxyphenyl)-7,9,10,11a,12,16b-hexahydro-8H-5,8-ethano-11,18-methanobenzo[f]indeno[2,1-b][1]azacyclotridecin-8-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 22 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere 19.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 20.1: lithium iodide / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 24 h / 0 °C / Inert atmosphere 22.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 36 h / 80 °C / Inert atmosphere
  • 43
  • [ 5411-61-0 ]
  • (6aS,11bS)-2,11-dimethoxy-13-(4-methoxy-4'-methyl-[1,1'-biphenyl]-2-yl)-6a,7-dihydro-5H-11b,6-prop[1]enoindeno[2,1-c]isoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 23 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere 19.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 20.1: lithium iodide / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 24 h / 0 °C / Inert atmosphere 22.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 36 h / 80 °C / Inert atmosphere 23.1: toluene; water / 6 h / 110 °C / Inert atmosphere
  • 44
  • [ 5411-61-0 ]
  • C21H22BrNO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux
  • 45
  • [ 5411-61-0 ]
  • (7aS)-6-bromo-2,2-dichloro-3-methoxy-2a-(3-methoxyphenyl)-2,2a,7,7a-tetrahydro-1H-cyclobuta[a]inden-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere
  • 46
  • [ 5411-61-0 ]
  • C18H21NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere
  • 47
  • [ 5411-61-0 ]
  • C27H26INO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere
  • 48
  • [ 5411-61-0 ]
  • (3aR,8aS)-7-bromo-3,3-dichloro-4-methoxy-3a-(3-methoxyphenyl)-3,3a,8,8atetrahydroindeno[2,1-b]pyrrol-2(1H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere
  • 49
  • [ 5411-61-0 ]
  • C19H16BrNO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux
  • 50
  • [ 5411-61-0 ]
  • C27H26INO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere
  • 51
  • [ 5411-61-0 ]
  • C23H25BrNO6(1-)*Na(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere
  • 52
  • [ 5411-61-0 ]
  • C35H38INO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 21 steps 1.1: magnesium / tetrahydrofuran / 4 h / Inert atmosphere; Reflux 1.2: 42 h / 20 °C / Inert atmosphere 1.3: 3 h / Inert atmosphere; Dean-Stark; Reflux 2.1: zinc; trichlorophosphate / diethyl ether / 96 h / 20 °C / Inert atmosphere 3.1: mesitylenesulfonylhydroxylamine; sodium sulfate / dichloromethane / 72 h / 20 °C / Inert atmosphere 4.1: methanol / 48 h / Inert atmosphere; Reflux 5.1: perchloric acid; water / tetrahydrofuran / 14 h / Inert atmosphere; Reflux 6.1: triethylamine; dmap / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere 7.1: dihydrogen peroxide; sodium hydroxide / water; methanol / 6 h / 20 °C / Inert atmosphere 8.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 9.1: hydrogen; 5%-palladium/activated carbon; sodium acetate / methanol / 12 h / 20 °C 10.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 8 h / 20 °C / Inert atmosphere 12.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h / 20 °C / Inert atmosphere 13.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere 14.1: potassium carbonate / methanol / 24 h / 60 °C / Inert atmosphere 15.1: dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-Tetramethyldisiloxane / toluene / 2.5 h / 50 °C / Microwave irradiation; Sealed tube; Inert atmosphere 16.1: dichloromethane / 12 h / 20 °C / Inert atmosphere 17.1: sodium hydroxide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride / tetrahydrofuran; water / 36 h / 20 °C / Inert atmosphere 18.1: potassium carbonate; methanol / 6 h / 20 °C / Inert atmosphere 19.1: triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere 20.1: lithium iodide / tetrahydrofuran / 8 h / 60 °C / Inert atmosphere 21.1: trifluoroacetic acid / dichloromethane / 24 h / 0 °C / Inert atmosphere
  • 53
  • [ 5411-61-0 ]
  • C10H9BrO [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With methanol; sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 4h; 4-1 Synthesis Example 4-1 In a 300 mL reactor, 9.74 g (40.4 mmol) of 4-bromo-7-methoxy-1-indanone, 35 mL of tetrahydrofuran and 15 mL of methanol were charged and stirred. The solution is cooled to 0 ° C.Sodium hydroborate 3.17 g (38.2 mmol) was addedThe solution was added little by little and stirred at room temperature for 4 hours. The solution was cooled to 0 ° C., 1.0 M aqueous hydrochloric acid solution was slowly added, the solubles were extracted with ethyl acetate, the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate.After filtering magnesium sulfate, of the residue obtained by distilling off the filtrate, 2.98 g (about 12.3 mmol) is taken in a 300 mL reactor, 150 mL of toluene, p-toluenesulfonic acid monohydrate 0.02 g (0.09 mmol) was added and heated in an 80 ° C. oil bath for 6 hours. The reaction mixture was cooled to room temperature, a saturated aqueous sodium hydrogen carbonate solution was added, the solubles were extracted with n-hexane and ethyl acetate, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate . After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the following formula (A-4a)1.77 g (yield 64%) of the desired product (hereinafter referred to as compound (A-4a)) shown in 1. was obtained.
64% With sodium tetrahydroborate; sodium methylate; toluene-4-sulfonic acid In tetrahydrofuran; methanol at 0 - 20℃; for 4h; 2-1 Synthesis Example 2-1 In a 300 mL reactor,4-Bromo-7-methoxy-1-indanone (9.74 g, 40.4 mmol), tetrahydrofuran (35 mL) and methanol (15 mL) were charged and stirred.This solution was cooled to 0 ° C., 3.17 g (38.2 mmol) of sodium hydroborate was slowly added little by little, and the mixture was stirred at room temperature for 4 hours. This solution was cooled to 0 ° C., 1.0 M hydrochloric acid aqueous solution was slowly added, the soluble matter was extracted with ethyl acetate, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. 2.98 g (about 12.3 mmol) of the residue obtained by filtering the magnesium sulfate and then distilling off the filtrate was placed in a 300 mL reactor, and 150 mL of toluene and p-toluenesulfonic acid monohydrate were taken. 0.02 g (0.09 mmol) was added, and the mixture was heated in an oil bath at 80 ° C. for 6 hours. After cooling the reaction solution to room temperature,Aqueous sodium hydrogen carbonate solution was added, and the soluble matter was extracted with n-hexane and ethyl acetate. The obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. The residue obtained by filtering magnesium sulfate and then distilling the filtrate off was purified by silica gel column chromatography to obtain the target compound represented by the following formula (A-2a) (hereinafter referred to as compound (A-2a)). Was obtained 1.77 g (yield 64%).
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