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[ CAS No. 21987-25-7 ] {[proInfo.proName]}

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Chemical Structure| 21987-25-7
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Product Details of [ 21987-25-7 ]

CAS No. :21987-25-7 MDL No. :MFCD13178623
Formula : C10H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :YSOFHURJVUIKMU-UHFFFAOYSA-N
M.W : 161.20 Pubchem ID :11137444
Synonyms :

Calculated chemistry of [ 21987-25-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.2
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 49.76
TPSA : 25.02 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) : -5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 2.48
Log Po/w (MLOGP) : 1.53
Log Po/w (SILICOS-IT) : 2.98
Consensus Log Po/w : 2.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.83
Solubility : 0.24 mg/ml ; 0.00149 mol/l
Class : Soluble
Log S (Ali) : -2.55
Solubility : 0.458 mg/ml ; 0.00284 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.79
Solubility : 0.0263 mg/ml ; 0.000163 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.24

Safety of [ 21987-25-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280 UN#:N/A
Hazard Statements:H302-H317 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 21987-25-7 ]

* 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 [ 21987-25-7 ]

[ 21987-25-7 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 96-48-0 ]
  • [ 21987-25-7 ]
  • [ 105664-56-0 ]
YieldReaction ConditionsOperation in experiment
82% With potassium carbonate In N,N-dimethyl acetamide for 48h; Heating;
  • 2
  • [ 111795-96-1 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
90% With hydrogen at 20℃; for 24h; Schlenk technique;
77% With hydrogen; acetic acid In ethanol for 2h; Ambient temperature;
Multi-step reaction with 2 steps 1: 99 percent / H2 / PtO2 / aq. ethanol; ethyl acetate 2: 70 percent / DIBALH / benzene / 1.5 h / 0 °C
  • 3
  • [ 155056-15-8 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
70% With diisobutylaluminium hydride In benzene at 0℃; for 1.5h;
  • 5
  • [ 21987-25-7 ]
  • [ 98-09-9 ]
  • [ 168143-69-9 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 5-methoxy-3-methyl-1H-indole With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 2.33333h; Stage #2: benzenesulfonyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 4.5h;
With n-butyllithium 1.) THF, hexane, a) -78 deg C, 20 min, b) RT, 2 h, 2.) THF, hexane, a) -78 deg C, 30 min, b) RT, 4 h; Yield given. Multistep reaction;
  • 6
  • [ 16381-50-3 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
93.6% With quinoline; copper for 2.5h; Heating;
With quinoline; copper for 2.5h; Heating; Yield given;
  • 7
  • [ 122-20-3 ]
  • [ 104-94-9 ]
  • [ 1076-74-0 ]
  • [ 21987-25-7 ]
  • 8
  • [ 93816-90-1 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
83% With ammonia; sodium In tetrahydrofuran at -33℃; for 1.5h;
  • 9
  • [ 21987-25-7 ]
  • [ 168143-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating
Multi-step reaction with 2 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating
Multi-step reaction with 2 steps 1: 95 percent / DMAP / acetonitrile / 12 h / Ambient temperature 2: 92 percent / N-bromosuccinimide, AIBN / CCl4 / 1 h / Heating
Multi-step reaction with 2 steps 1: dmap / acetonitrile / 20 °C 2: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / cyclohexane / Reflux

  • 10
  • [ 21987-25-7 ]
  • (+)-10-methoxyaffinisine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 14.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 15.1: potassium tert-butoxide / benzene / 1 h / 20 °C 15.2: tetrahydrofuran; benzene / 24 h / 20 °C 15.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 16.1: 90 percent / sodium borohydride / methanol / 8 h / 0 °C
Multi-step reaction with 15 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 13.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 14.1: potassium tert-butoxide / benzene / 1 h / 20 °C 14.2: tetrahydrofuran; benzene / 24 h / 20 °C 14.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 15.1: 90 percent / sodium borohydride / methanol / 8 h / 0 °C
Multi-step reaction with 18 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C 16: t-BuOK / benzene; tetrahydrofuran 17: aq.HCl / tetrahydrofuran / 55 °C 18: 90 percent / NaBH4 / methanol / 0 °C
  • 11
  • [ 21987-25-7 ]
  • [ 600136-05-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 12 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C
Multi-step reaction with 11 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C
Multi-step reaction with 13 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr
  • 12
  • [ 21987-25-7 ]
  • [ 409095-15-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 14 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 14.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C
Multi-step reaction with 13 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 13.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C
Multi-step reaction with 15 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C
  • 13
  • [ 21987-25-7 ]
  • [ 63959-49-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 15 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 14.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 15.1: potassium tert-butoxide / benzene / 1 h / 20 °C 15.2: tetrahydrofuran; benzene / 24 h / 20 °C 15.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C
Multi-step reaction with 14 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 13.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 14.1: potassium tert-butoxide / benzene / 1 h / 20 °C 14.2: tetrahydrofuran; benzene / 24 h / 20 °C 14.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C
Multi-step reaction with 17 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C 16: t-BuOK / benzene; tetrahydrofuran 17: aq.HCl / tetrahydrofuran / 55 °C
  • 14
  • [ 21987-25-7 ]
  • [ 600136-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 14.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 15.1: potassium tert-butoxide / benzene / 1 h / 20 °C 15.2: tetrahydrofuran; benzene / 24 h / 20 °C 15.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 16.1: 81 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C
Multi-step reaction with 15 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 13.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 14.1: potassium tert-butoxide / benzene / 1 h / 20 °C 14.2: tetrahydrofuran; benzene / 24 h / 20 °C 14.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 15.1: 81 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C
Multi-step reaction with 18 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C 16: t-BuOK / benzene; tetrahydrofuran 17: aq.HCl / tetrahydrofuran / 55 °C 18: 90 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C
  • 15
  • [ 21987-25-7 ]
  • [ 600136-06-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 13 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C
Multi-step reaction with 12 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C
Multi-step reaction with 14 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran
  • 16
  • [ 21987-25-7 ]
  • (+)-Na-methylsarpagine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 17 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 5 h / 0 °C 8.1: 25 g / sodium borohydride / ethanol / 4 h / -10 - -5 °C 9.1: AcOH / CH2Cl2 / 20 °C 9.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 10.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 11.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 12.1: HCl / ethanol 12.2: H2 / Pd/C / ethanol / 12 h / 20 °C 13.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 14.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 15.1: potassium tert-butoxide / benzene / 1 h / 20 °C 15.2: tetrahydrofuran; benzene / 24 h / 20 °C 15.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 16.1: 81 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C 17.1: 90 percent / sodium borohydride / ethanol / 4 h / 0 °C
Multi-step reaction with 16 steps 1.1: 95 percent / DMAP / acetonitrile / 12 h / 20 °C 2.1: N-bromosuccinimide; AIBN / CCl4 / 0.67 h / Heating 3.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3.2: 93 percent / tetrahydrofuran / -78 - 20 °C 4.1: xylene / 48 h / Heating 5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 5.2: 35 g / tetrahydrofuran / 18 h / 20 °C 6.1: aq. HCl / tetrahydrofuran / 0.67 h / 20 °C 7.1: ethanol / 25 °C 8.1: AcOH / CH2Cl2 / 20 °C 8.2: 82 percent / TFA / CH2Cl2 / 240 h / 20 °C 9.1: 83 percent / sodium hydride; methanol / toluene / 4 h / Heating 10.1: 82 percent / aq. KOH / dioxane / 48 h / Heating 11.1: HCl / ethanol 11.2: H2 / Pd/C / ethanol / 12 h / 20 °C 12.1: 1.3 g / K2CO3 / tetrahydrofuran / 20 - 60 °C 13.1: 81 percent / PPh3; Bu4NBr; K2CO3 / Pd(OAc)2 / dimethylformamide; H2O / 5 h / 70 °C 14.1: potassium tert-butoxide / benzene / 1 h / 20 °C 14.2: tetrahydrofuran; benzene / 24 h / 20 °C 14.3: 90 percent / aq. HCl / tetrahydrofuran / 6 h / 55 °C 15.1: 81 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C 16.1: 90 percent / sodium borohydride / ethanol / 4 h / 0 °C
Multi-step reaction with 19 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C 16: t-BuOK / benzene; tetrahydrofuran 17: aq.HCl / tetrahydrofuran / 55 °C 18: 90 percent / BBr3 / CH2Cl2 / 3 h / -78 - 20 °C 19: 90 percent / NaBH4 / ethanol
  • 17
  • [ 21987-25-7 ]
  • (2S,6S,12bS)-3-Eth-(E)-ylidene-9-methoxy-13-[1-methoxy-meth-(E)-ylidene]-12-methyl-1,3,4,7,12,12b-hexahydro-2H,6H-2,6-methano-indolo[2,3-a]quinolizine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 16 steps 1: 95 percent / DMAP / acetonitrile 2: 90 percent / NBS; AIBN / cyclohexane / Heating 3: 93 percent / n-BuLi / tetrahydrofuran / -78 °C 4: xylene / Heating 5: NaH / dimethylformamide / 20 °C 6: 95 percent / aq. HCl / tetrahydrofuran 7: ethanol / 2 h / 0 °C 8: NaBH4 / -5 °C 9: HOAc / CH2Cl2 10: TFA / CH2Cl2 / 240 h 11: 83 percent / NaH / methanol; toluene / Heating 12: 82 percent / aq. KOH / dioxane / Heating 13: 92 percent / H2; HCl / Pd/C / ethanol / 20 °C / 760.05 Torr 14: K2CO3 / tetrahydrofuran 15: 81 percent / PPh3; K2CO3; n-Bu4NBr / Pd(OAc)2 / dimethylformamide; H2O / 70 °C 16: t-BuOK / benzene; tetrahydrofuran
  • 18
  • [ 1006-94-6 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: BuLi / tetrahydrofuran; hexane / 0.25 h / -10 °C 1.2: tetrahydrofuran; hexane / 3 h / 0 °C 2.1: 5.4 g / NBS / tetrahydrofuran; hexane / 3 h / -78 °C 3.1: t-BuLi / pentane; tetrahydrofuran / 0.17 h / -78 °C 3.2: pentane; tetrahydrofuran / 0.25 h / -78 °C 3.3: Bu4NF / tetrahydrofuran / 0.17 h / 20 °C
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 0 - 40 °C 1.2: 1 h / 90 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 0 - 20 °C / Schlenk technique
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2.5 h / 0 - 40 °C 1.2: 1 h / 90 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 0 - 20 °C
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2.5 h / 0 - 40 °C 1.2: 1 h / 90 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 0 - 20 °C / Schlenk technique
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 0 - 40 °C 1.2: 1 h / 90 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 20 °C
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2.5 h / 0 - 40 °C / Inert atmosphere 1.2: 1 h / 90 °C / Inert atmosphere 2.1: lithium aluminium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 2 h / 40 °C / Inert atmosphere 1.2: 1 h / 90 °C / Inert atmosphere 2.1: lithium aluminium hydride / tetrahydrofuran / 20 °C / Schlenk technique; Inert atmosphere

  • 19
  • [ 100-17-4 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 85 percent / t-BuOK / dimethylformamide / 2.5 h / -23 °C 2: 98 percent / K2CO3, 18-crown-6 / acetonitrile / 12 h / Heating 3: 99 percent / H2 / PtO2 / aq. ethanol; ethyl acetate 4: 70 percent / DIBALH / benzene / 1.5 h / 0 °C
Multi-step reaction with 2 steps 1: 30 percent / tBuOK / dimethylformamide / -20 - -10 °C 2: 77 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature
Multi-step reaction with 3 steps 1: 65 percent / tBuOK / dimethylformamide / 0.5 h / -20 - -10 °C 2: 89 percent / anhydrous K2CO3, <18>crown-6 / acetonitrile / Heating 3: 77 percent / H2, acetic acid / Pd/C (10percent Pd) / ethanol / 2 h / 2280 Torr / Ambient temperature
Multi-step reaction with 3 steps 1: potassium <i>tert</i>-butylate / N,N-dimethyl-formamide / 2.5 h / -24 °C 2: potassium carbonate / dimethyl sulfoxide 3: hydrogen / 24 h / 20 °C / 760.05 Torr / Schlenk technique

  • 20
  • [ 21987-25-7 ]
  • 6,7,8,9-Tetrahydro-2-methoxy-8,8,10-trimethyl-9-(1-pyrrolidinyl)-pyrido[1,2-a]indole Hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.1 g (82%) With potassium carbonate In ISOPROPYLAMIDE; toluene 15 6,7,8,9-Tetrahydro-2-methoxy-8,8,10-trimethyl-9-(1-pyrrolidinyl)-pyrido[1,2-a]indole Hydrochloride Anhydrous potassium carbonate (62 g, 0.45 mol) was added to a solution of 5-methoxy-3-methylindole (29 g, 0.18 mol, prepared according to E. Young (formylation) and R. Heacock (reduction), J. Chem. Soc., 1958, 3493 and Can. J. Chem., 42, 514, (1964) respectively) and γ-butyrolactone (77.5 g, 0.9 mol) in dimethylacetamide (1100 mL). Under mechanical stirring and protected with a drying tube, the reaction mixture was refluxed for 18 hours. More γ-butyrolactone (39 g, 0.45 mol) was added, and the reflux was continued for 12 hours. A final portion of γ-butyrolactone (19 g, 0.22 mol) was added and the thick suspension was refluxed for another 12 hours, cooled to ~30° C., and poured into water (1000 mL). Toluene (1000 mL) was added and the 2 phase system was vigorously stirred for 15 minutes. The aqueous layer was separated and acidified to pH2 with concentrated hydrochloric acid. The product was extracted with toluene (3*400 mL). The combined extracts were washed with water (1000 mL), dried over MgSO4, filtered, and evaporated to afford the title product 36.1 g (82%) m.p. 69°-71° C. This acid was used in the next step without further purification. NMR (DMSO-d6) δ2.24 (s, 3H, CH3), 1.6-2.4 (m, 4H, CH2 CH2 -CO), 3.78 (s, 3H, CH3 O), 4.1 (obscured triplet, J=6.5 H, 2H, CH2 -N), 6.79 (dd, Jo=9 Hz, Jm=2 Hz, 1H, H-6), 6.98 (br s, 1H, H-2), 7.01 (s, 1H, H-4), 7.38 (d, Jo=9 Hz, 1H, H-7); MS (Relative intensity, fragment) m/e 247 (46, M+), 232 (5, M-CH3), 174 (100, loss of CH2 CH2 COOH), 160 (8, 232-acrylic acid)
  • 21
  • [ 288-32-4 ]
  • [ 21987-25-7 ]
  • 5-methoxy-3-methyl-2-(1-imidazolyl)indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bromine In 1,4-dioxane 11 EXAMPLE 11 A solution of bromine (0.62 ml) in dioxane (25 ml) is added dropwise over a period of 2 hours to a mixture of 5-methoxy-3-methylindole (2.00 g) and imidazole (4.08 g) in dioxane (50 ml) while stirring at 10°. Upon complete addition cooling bath is removed and the suspension is stirred two days at room temperature. The mixture is concentrated in vacuo and the oil obtained is suspended in ether (100 ml) and extracted into 1N hydrochloric acid (2*50 ml). The acid extract is first washed with ether (1*50 ml), the pH is adjusted to pH 6 with 3N sodium hydroxide (38 ml), and the aqueous mixture is then extracted with ether (8*50 ml). This extract is dried over magnesium sulfate, filtered, and concentrated in vacuo to give an oil. This oil is purified by flash chromatography on silica gel (eluent: 95% methylene chloride, 5% methanol) to give 2-(1-imidazolyl)-5-methoxy-3-methylindole as a crystalline solid; NMR (CDCl3): δ10.4 (s, 1H), 7.67 (s, 1H), 3.88 (s, 3H), 2.22 (s, 3H).
  • 22
  • [ 16620-52-3 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
In ethanol 11 EXAMPLE 11 A solution of 5-methoxygramine (3.96 g) in absolute ethanol (80 ml) with 10% Palladium on carbon (0.40 g) is hydrogenated at atmospheric pressure for 10 hours. The catalyst is removed by vacuum filtration through Hy-Flo and the filtrate is concentrated in vacuo to give an oil which crystallizes on standing to give 5-methoxy-3-methylindole.
  • 23
  • [ 21987-25-7 ]
  • [ 1068975-53-0 ]
YieldReaction ConditionsOperation in experiment
38% Stage #1: 5-methoxy-3-methyl-1H-indole With potassium <i>tert</i>-butylate In N,N-dimethyl-formamide at 20℃; for 0.75h; Stage #2: With chloroamine In diethyl ether; N,N-dimethyl-formamide at 20℃; for 2.25h; Stage #3: With water In ethyl acetate 153.1 Example 153; 2-(3-Fluoro-phenyl)-4-methyl-pyrimidine-5-carboxylic acid (5-methoxy-3-methyl-indol- 1 -vD- amide; Step 1 : A solution of potassium tert-butoxide (5.23 g, 46.62 mmol) and 5-methoxy-3- methylindole (3.41 g, 21.15 mmol) in DMF (20 mL) is stirred at rt for 45 min. A solution of monochloroamine in ether (400 mL, 60 mmol) is added via an addition funnel over 15 min. The resulting mixture is stirred for 2 h. The solvent is removed and the residue is partitioned between EtOAc and water. The organic phase is separated, washed with saturated aqueous NaHCθ3, water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by column chromatography eluting with 10% EtOAc in heptane to afford 5-methoxy- 3-methyl-indol- 1 -ylamine (1.42 g, 38%) as a solid. MS: 176 (M+H); 1H NMR (300MHz, CDCl3): δ 7.26-7.23 (m, IH), 6.98-6.97 (m, IH), 6.91-6.87 (m, 2H), 4.64 (br s, 2 H), 3.86 (s, 3H), 2.26-2.25 (m, 3H).
  • 24
  • [ 21987-25-7 ]
  • [ 3746-67-6 ]
  • [ 1146972-70-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 25℃; for 1.25h; Stage #2: 3-(acetylamino)-4-methoxybenzensulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 24.3333h; 1 Sodium hydride (2.15 grams, 49.3 mmol) was taken into a 250 mL three- necked round bottom flask containing tetrahydrofuran (50 mL) under nitrogen atmosphere. Added a solution of 5-methoxy-3-methyl indole solution (5.3 grams, 32.9 mmol) in tetrahydrofuran (25 mL) to the above mixture at 25 0C, over a period of 15 minutes. The above reaction mass was stirred further for a period of 1 hour and mass was cooled to 0 0C and a solution of 3-acetamido-4-methoxy benzenesulfonyl chloride (13.01 grams, 49.3 mmol) in tetrahydrofuran (65 mL) was added through a dropping funnel over a period of 20 minutes. This mass was allowed to cool to rυυm temperature and stirred over night (~ 24 hours). The progress of the reaction was monitored by thin layer chromatography. After completion of the reaction it was quenched into ice λvater (100 mL) under stirring and extracted the product with ethylacetate (2 x 250 mL). Organic phase was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain thick syrupy mass, which was used as such for the next step without purification. Mass (m/z): 389.4 (M+H)+;
Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 25℃; Inert atmosphere; Stage #2: 3-(acetylamino)-4-methoxybenzensulfonyl chloride In tetrahydrofuran at 0 - 30℃; Inert atmosphere; 1 Preparation 1: 1-(3-Acetamido-4-methoxy benzenesulfonyl)-5-methoxy-3-methyl-1H-indoleSodium hydride (2.15 grams, 49.3 mmol) was taken into a 250 mL three-necked round bottom flask containing tetrahydrofuran (50 mL) under nitrogen atmosphere. Added a solution of 5-methoxy-3-methyl indole solution (5.3 grams, 32.9 mmol) in tetrahydrofuran (25 mL) to the above mixture at 25° C., over a period of 15 minutes. The above reaction mass was stirred further for a period of 1 hour and mass was cooled to 0° C. and a solution of 3-acetamido-4-methoxy benzenesulfonyl chloride (13.01 grams, 49.3 mmol) in tetrahydrofuran (65 mL) was added through a dropping funnel over a period of 20 minutes. This mass was allowed to cool to room temperature and stirred over night (24 hours). The progress of the reaction was monitored by thin layer chromatography. After completion of the reaction it was quenched into ice water (100 mL) under stirring and extracted the product with ethylacetate (2×250 mL). Organic phase was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain thick syrupy mass, which was used as such for the next step without purification.Mass (m/z): 389.4 (M+H)+;
10.2 g Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In tetrahydrofuran at 25℃; for 1h; Inert atmosphere; Stage #2: 3-(acetylamino)-4-methoxybenzensulfonyl chloride In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;
  • 25
  • [ 21987-25-7 ]
  • [ 1002916-43-9 ]
  • [ 1004548-18-8 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: 5-methoxy-3-methyl-1H-indole; 4-butyl-4-(dimethylamino)cyclohexanone With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 24h; Stage #2: With sodium hydroxide In dichloromethane at 20℃; for 0.333333h; 125; 126 5-Methoxyskatole (Ind-9, 806 mg, 5 mmol) was dissolved in methylene chloride (40 ml) together with Ket-4 (985 mg, 5 mmol), and trifluoromethanesulfonic acid (0.65 ml, 7.5 mmol) was added. The mixture was stirred at RT for 24 h.-For working up, 2 N NaOH (20 ml) was added to the reaction mixture and the mixture was stirred at RT for 20 min. After the organic phase had been separated off, the aqueous phase was extracted with methylene chloride (3×20 ml). The combined organic extracts were dried over Na2SO4 and then concentrated. The crude product was obtained in a yield of 1.69 g (99%) as a yellow oil and was employed in the next reaction without further purification.
  • 26
  • [ 21987-25-7 ]
  • [ 7594-43-6 ]
  • [ 1220093-81-1 ]
YieldReaction ConditionsOperation in experiment
55% With camphor-10-sulfonic acid In dichloromethane at 20℃; for 2h; Molecular sieve;
  • 27
  • [ 887144-94-7 ]
  • [ 21987-25-7 ]
  • [ 1257268-87-3 ]
YieldReaction ConditionsOperation in experiment
72% With copper (I) acetate In methanol at 20℃; for 18h; Inert atmosphere; regioselective reaction;
  • 28
  • [ 21987-25-7 ]
  • [ 35356-70-8 ]
  • (+/-)-exo-methyl 1-acetyl-5-methoxy-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate [ No CAS ]
  • (+/-)-endo-methyl 1-acetyl-5-methoxy-3a-methyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 66% 2: 18% With zirconium(IV) chloride In dichloromethane at 20℃; for 24h; optical yield given as %de; diastereoselective reaction;
  • 29
  • [ 1308803-37-3 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
75% With carbon monoxide; [Rh(CO)2(Me2NCH2CH2NMe2)][RhCl2(CO)2] In tetrahydrofuran at 100℃; for 20h; Autoclave;
  • 30
  • [ 30879-49-3 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / dimethyl sulfoxide / 20 h / 20 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C 2.2: 15 h / 0 - 20 °C 3.1: [Rh(CO)2(Me2NCH2CH2NMe2)][RhCl2(CO)2]; carbon monoxide / tetrahydrofuran / 20 h / 100 °C / 5171.62 Torr / Autoclave
  • 32
  • [ 10601-19-1 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
98.5% With N,N,N,N,N,N-hexamethylphosphoric triamide; hydrazine hydrate monohydrate; potassium hydroxide at 120℃; Green chemistry; 7-9 Example 7 16.16 g (99%, 0.1 mol) of 5-methoxyindole-3-carbaldehyde and 9.15 g (92%, 0.15 mol) of potassium hydroxide, 7.65 g (98%, 0.15 mol) of hydrazine hydrate and 100 mL of hexamethylphosphoramide was placed in a round bottom flask. Stirring and refluxing reaction for 1 h, Continue heating to distill off the water and the pre-fraction. Continue to heat up to 120 ° C, Keep warm for 2~3h, Then the solvent was distilled off under reduced pressure. Processed 5-methoxy-3-methylindole 15.84g, Product purity is 99.5%, 5-methoxyindole-3-formaldehyde conversion rate 100.0%, The yield of 5-methoxy-3-methylindole was 98.5%.
40% With lithium aluminium hydride In tetrahydrofuran at 20℃; Schlenk technique; Inert atmosphere;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃; Schlenk technique;
Multi-step reaction with 2 steps 1: lithium aluminium hydride / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere 2: sodium hydroxide; magnesium(II) sulfate / lithium hydroxide monohydrate; diethyl ether / 0.5 h / 0 °C
400 mg With lithium aluminium hydride In tetrahydrofuran for 3h; Inert atmosphere; Reflux; 1C.76.A Preparation of 5-methoxy-3-methyl-1H-indole To a solution of 5-methoxy-1H-indole-3-carbaldehyde (500 mg, 2.854 mmol) in THF (10 mL) at room temperature was added a 2M solution of LiAlH4in THF (2.846 mL, 5.691 mmol) drop wise under nitrogen. The reaction mixture was stirred for 3 h at reflux. After cooled down in an ice-water bath, the reaction was quenched carefully with water (216 μL), aqueous 15% NaOH solution (216 μL) and water (3 x 216 μL). The mixture was filtered, the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound (400 mg) as an oil. LCMS m/z = 162.2 [M+H]+; NMR (400 MHz, CDC13) δ ppm 2.31 (d, J = 1.1 Hz, 3H), 3.88 (s, 3H), 6.86 (dd, J = 8.7 and 2.4 Hz, 1H), 6.94-6.97 (m, 1H), 7.02 (d, J = 2.4 Hz, 1H), 7.24 (dd, J = 8.8 and 0.4 Hz, 1H), 7.76 (bs, 1H).
225 mg With lithium aluminium hydride In tetrahydrofuran at 20℃;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃; for 12h; Inert atmosphere;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃; Schlenk technique;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃; for 12h;
With lithium aluminium hydride In tetrahydrofuran at 20℃;
With lithium aluminium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference: [1]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN109678780, 2019, A Location in patent: Paragraph 0031-0033
[2]Chang, Rong; Gao, Xuebo; Guo, Zhen; Hao, Danyang; Rao, Junxin; Zhang, Zhuxia; Zhou, Cong-Ying [Journal of Organic Chemistry, 2022]
[3]Cheng, Hong-Gang; Lu, Liang-Qiu; Wang, Tao; Yang, Qing-Qing; Liu, Xiao-Peng; Li, Yang; Deng, Qiao-Hui; Chen, Jia-Rong; Xiao, Wen-Jing [Angewandte Chemie - International Edition, 2013, vol. 52, # 11, p. 3250 - 3254][Angew. Chem., 2013, vol. 125, # 11, p. 3332 - 3336,5]
[4]Beaud, Rodolphe; Guillot, Regis; Kouklovsky, Cyrille; Vincent, Guillaume [Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500]
[5]Current Patent Assignee: PFIZER INC - WO2015/66344, 2015, A1 Location in patent: Page/Page column 233
[6]Shao, Changdong; Shi, Guangfa; Zhang, Yanghui; Pan, Shulei; Guan, Xiaohong [Organic Letters, 2015, vol. 17, # 11, p. 2652 - 2655]
[7]Chen, Weiliang; Xia, Yong; Lin, Lili; Yuan, Xiao; Guo, Songsong; Liu, Xiaohua; Feng, Xiaoming [Chemistry - A European Journal, 2015, vol. 21, # 43, p. 15104 - 15107]
[8]Zhou, Zijun; Li, Yanjun; Gong, Lei; Meggers, Eric [Organic Letters, 2017, vol. 19, # 1, p. 222 - 225]
[9]Wang, Shuai; Shen, Yao-Bin; Li, Long-Fei; Qiu, Bin; Yu, Liping; Liu, Qing; Xiao, Jian [Organic Letters, 2019, p. 8904 - 8908]
[10]Bai, Jian-Fei; Zhao, Lulu; Wang, Fang; Yan, Fachao; Kano, Taichi; Maruoka, Keiji; Li, Yuehui [Organic Letters, 2020, vol. 22, # 14, p. 5439 - 5445]
[11]Xie, Tao; Sui, Qi-Bang; Qin, Lu-Zhe; Wen, Xiaoan; Sun, Hongbin; Xu, Qing-Long; Zhen, Le [Journal of Organic Chemistry, 2021, vol. 86, # 8, p. 5518 - 5529]
[12]Devi, Manju; Jadhav, Amol P.; Singh, Ravi P. [New Journal of Chemistry, 2021, vol. 45, # 19, p. 8445 - 8448]
  • 33
  • [ 887144-94-7 ]
  • [ 21987-25-7 ]
  • [ 1257268-87-3 ]
  • C12H9F6NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 60% 2: 19% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 0.25h; Schlenk technique; Inert atmosphere;
1: 35% 2: 42% With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
  • 34
  • [ 21987-25-7 ]
  • [ 3278-34-0 ]
  • [ 1449683-70-8 ]
  • 35
  • [ 67-56-1 ]
  • [ 21987-25-7 ]
  • [ 1598420-17-7 ]
YieldReaction ConditionsOperation in experiment
65% With copper acetylacetonate; 1-azido-1λ3-benzo[d][1,2]iodaoxol-3(1H)-one at 60℃; for 1.5h; Schlenk technique; Inert atmosphere; regioselective reaction;
  • 36
  • [ 21987-25-7 ]
  • [ 616-83-1 ]
  • C17H16N2O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0 - 20℃;
  • 37
  • [ 21987-25-7 ]
  • [ 87751-69-7 ]
  • C25H23NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With bis(η3-allyl-μ-chloropalladium(II)); N-((1S,2R)-2-((R)-(4-bromophenyl)sulfinyl)-1,2-diphenylethyl)-2-(diphenylphosphino)benzamide; caesium carbonate In dichloromethane at 40℃; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 38
  • [ 21987-25-7 ]
  • 5-methoxy-3-methylindoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylsilane; trifluoroacetic acid at 20℃; Inert atmosphere; 1C.76.B Preparation of 5-methoxy-3-methylindoline To a solution of 5-methoxy-3-methyl-lH-indole (400 mg, 2.481 mmol) in TFA (5 mL) at room temperature was added triethylsilane (1.585 mL, 9.926 mmol) dropwise under nitrogen. The reaction mixture was stirred at room temperature overnight. The mixture was concentrated, diluted with ethyl acetate, washed with saturated aqueous NaHC03solution, dried over anhydrous Na2S04, filtered then concentrated. The residue was purified by silica gel column chromatography to give the title compound (200 mg) as orange oil. LCMS m/z = 164.2 [M+H]+; NMR (400 MHz, CDC13) δ ppm 1.31 (d, J = 6.8 Hz, 3H), 3.10 (t, J = 8.7 Hz, 1H), 3.27-3.38 (m, 1H), 3.50 (br, 1H), 3.68 (t, J = 8.6 Hz, 1H), 3.76 (s, 3H), 6.57-6.62 (m, 2H), 6.72-6.75 (m, 1H).
With sodium cyanoborohydride; acetic acid at 0 - 20℃; for 4h;
  • 39
  • [ 21987-25-7 ]
  • [ 667-27-6 ]
  • ethyl 2,2-difluoro-2-(5-methoxy-3-methyl-1H-indol-2-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 2h; Schlenk technique; Inert atmosphere;
  • 40
  • [ 21987-25-7 ]
  • [ 1443051-84-0 ]
YieldReaction ConditionsOperation in experiment
30% With copper(l) iodide; pyridinium chlorochromate In N,N-dimethyl-formamide at 100℃; for 24h; General procedure for the oxidation of 3 General procedure: After a mixture of CuI (4.4 mmol) and PCC (8 mmol) inDMF (30 mL) was stirred at room temperature for 30 min, 3 (4 mmol) was then added to the mixture andthe mixture was stirred at 100 °C for 24 h. After cooling, the resulting mixture was added to 10% aqueousHCl solution, extracted with AcOEt (100 mL), washed with brine, and dried over MgSO4. The solventwas removed, and the residue was purified by silica gel column chromatography with CH2Cl2 to give 1.
  • 41
  • [ 67-56-1 ]
  • [ 1006-94-6 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
94% With Co(BF4)2·6H2O; tris(2-diphenylphosphinoethyl)phosphine; potassium carbonate at 100℃; for 24h; Autoclave; Glovebox; Inert atmosphere;
85% With sodium hydroxide at 100℃; for 14h; Sealed tube; Autoclave; Inert atmosphere;
83% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; potassium-t-butoxide at 140℃; for 17h;
79% With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; potassium-t-butoxide at 140℃; for 24h; Schlenk technique; Sealed tube;
67% With tripotassium phosphate tribasic; C41H35FeN2O3P In neat (no solvent) at 110℃; for 16h; Inert atmosphere; Schlenk technique;
With rhenium(I) pentacarbonyl chloride; Cs2CO3; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 140℃; for 24h; Inert atmosphere; Sealed tube;
With bis[dichlorido(η5-1,2,3,4,5-pentamethyl-cyclopentadienyl)iridium(III)]; potassium-t-butoxide at 140℃; for 19h; Inert atmosphere;

  • 42
  • [ 21987-25-7 ]
  • [ 74-88-4 ]
  • [ 81784-54-5 ]
YieldReaction ConditionsOperation in experiment
48% With sodium hydride In tetrahydrofuran; mineral oil at 20℃; General Procedure A: N-methylation of Indole Derivatives General procedure: In a flame-dried flask, the indole (1.0 eq) was dissolved in THF (10 mL). Sodium hydride (60% w/w, 1.5 eq) was added in one portion, then methyl iodide (2.0 eq) was added dropwise. The reaction was stirred at rt until consumption of starting material was observed by TLC. The reaction was diluted with ethyl acetate (10 mL) and the excess NaH was quenched with water (15 mL). The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (3 x 10 mL). The combined organic layers were washed with brine (15 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by flash chromatography.
Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃;
  • 43
  • [ 21987-25-7 ]
  • [ 37051-70-0 ]
  • N-((5aR,10bS)-9-methoxy-10b-methyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In acetonitrile at 0℃; for 5h; enantioselective reaction;
  • 44
  • [ 21987-25-7 ]
  • 1-(but-3-en-1-yl)-5-methoxy-3-methylindole [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 24h;
  • 45
  • [ 21987-25-7 ]
  • [ 102-96-5 ]
  • (R)-5-methoxy-3-methyl-2-(2-nitro-1-phenylethyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With C42H33N3O2; zinc trifluoromethanesulfonate In toluene at 80℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction;
  • 46
  • [ 21987-25-7 ]
  • [ 143121-73-7 ]
  • 7-methoxy-9-methyl-1,3-diphenyl-9H-pyrrolo[1,2-a]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With copper(ll) bromide In chloroform at 20℃; for 0.5h;
  • 47
  • [ 21987-25-7 ]
  • C14H13NO4 [ No CAS ]
  • ethyl (3S,3'R)-7'-methoxy-3'-(5-methoxy-3-methyl-1H-indol-2-yl)-1,9'-dimethyl-2-oxo-2',3'-dihydrospiro[indoline-3,1'-pyrrolo[1,2-a]indole]-3'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With (R)-(+)-(4,4'-bi-1,3-benzodioxole)-5,5'-diylbis(di(3,5-dimethylphenyl)phosphine); bis-triphenylphosphine-palladium(II) chloride; silver hexafluoroantimonate at 25 - 90℃; for 5h; Inert atmosphere; stereoselective reaction;
  • 48
  • [ 21987-25-7 ]
  • C23H22N2O4 [ No CAS ]
  • ethyl (3S,3'R)-3'-(5-methoxy-3-methyl-1H-indol-2-yl)-1,9'-dimethyl-2-oxo-2',3'-dihydrospiro[indoline-3,1'-pyrrolo[1,2-a]indole]-3'-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With (R)-(+)-(4,4'-bi-1,3-benzodioxole)-5,5'-diylbis(di(3,5-dimethylphenyl)phosphine); bis-triphenylphosphine-palladium(II) chloride; silver hexafluoroantimonate at 90℃; for 6h; Inert atmosphere; stereoselective reaction;
  • 49
  • [ 21987-25-7 ]
  • C15H16N2O [ No CAS ]
  • C25H27N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: C15H16N2O With C48H46IrN8O6(1+)*C32H12BF24(1-) In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: 5-methoxy-3-methyl-1H-indole In toluene at 55℃; for 12h; Inert atmosphere; enantioselective reaction;
  • 50
  • [ 21987-25-7 ]
  • [ 101349-16-0 ]
YieldReaction ConditionsOperation in experiment
90% With tetrabutyl-ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -10℃; Green chemistry; 22.2 Example 22: Synthesis of 5-methoxy-3-methyl-1-hydrogen-oxindole Add the starting material 22 (32 mg, 0.2 mmol), tetrabutylammonium chloride hydrate (67 mg,0.24 mmol) to the same reactor, then add 1.5 mL of the solvent dichloromethane to control the reaction temperature to -10 °C, and then A 0.5 mL solution of [bis(trifluoroacetoxy)iodo]benzene (103 mg, 0.24 mmol) in dichloromethane was added dropwise, and the reaction was quickly confirmed by TLC. The reaction was quenched by the addition of 10 mL EtOAc EtOAc (EtOAc) Chromatography (petroleum ether / ethyl acetate, 5:1) gave 5-methoxy-3-methyl-1-hydro-oxindole 31.8 mg, yield 90%.
90% With tetrabutyl-ammonium chloride; water; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 25℃;
  • 51
  • [ 21987-25-7 ]
  • [ 61985-23-7 ]
  • [ 500342-88-1 ]
YieldReaction ConditionsOperation in experiment
72% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 12h; Inert atmosphere;
  • 52
  • [ 21987-25-7 ]
  • (E)-diethyl 5-diazo-4-oxohex-2-enedioate [ No CAS ]
  • diethyl 2-methoxy-10-methyl-7-oxo-6,7,8,9-tetrahydropyrido-[1,2-a]indole-6,9-dicarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 5-methoxy-3-methyl-1H-indole; (E)-diethyl 5-diazo-4-oxohex-2-enedioate With scandium tris(trifluoromethanesulfonate) In dichloromethane for 6h; Reflux; Stage #2: With rhodium (II) octanoate dimer In dichloromethane at 20℃; for 2h;
  • 53
  • [ 21987-25-7 ]
  • [ 1125-40-2 ]
YieldReaction ConditionsOperation in experiment
11% With boron tribromide; In n-heptane; dichloromethane; at 20℃; for 16.0h;Sealed tube; A solution of boron tribromide (190 muL, 1.0M in heptane, 190 mumol)was added to a solution of 5-methoxy-3-indole (15.3 mg, 95 mumol) inanhydrous DCM (1 mL). The reaction vessel was sealed and stirred atroom temperature for 16 h. The reaction was then quenched with water(10 mL) and extracted with DCM (3×10 mL). The organic extractswere combined, dried over MgSO4, and the solvent was removed underreduced pressure. The residue was purified by silica column chromatography(DCM followed by DCM/MeOH 99:1 v/v) to yield 8 (r.f. 0.66in DCM/MeOH 99:1 v/v) as a colorless oil (1.5 mg, 11%).1H NMR (400 MHz, CD3OD) delta 7.20 (dd, J=8.6, 0.6 Hz, 1H), 6.97(dd, J=2.5, 0.5 Hz, 1H), 6.95 (s, 1H), 6.76 (ddd, J=8.6, 2.5, 0.4 Hz,1H), 2.27 (d, J=1.1 Hz, 3H)2.22 (d, J=1.1 Hz, 3H), 6.64 (dd,J=8.6, 2.4 Hz, 1H), 6.85 (dd, J=2.4, 0.6, 1H), 6.91 (app q,J=1.2 Hz, 1H), 7.13 (dd, J=8.6, 0.6 1H); 13C NMR (101 MHz,CD3OD) delta 152.2, 131.0, 130.2, 124.0, 112.4, 112.1, 110.2, 103.5, 9.8;HRMS (ESI+) calculated for C9H10NO+ (M+H)+: 148.0757, found:148.0762.
  • 54
  • [ 1006-94-6 ]
  • [ 74-88-4 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
23% Stage #1: 5-methoxylindole With methylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 0.333333h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; diethyl ether for 120h; Inert atmosphere; regioselective reaction; 2.3. Synthesis of 5-Methoxy-3-methylindole (31) The methylation of 5-methoxyindole was based on the procedure byAmir-Heidari and Micklefield.19 Methylmagnesium bromide (1.75 mL,3.0M in diethyl ether, 5.25 mmol) was added to 5-methoxyindole(736 mg, 5.00 mmol) in anhydrous THF (10 mL) and stirred at roomtemperature for 20 min under an atmosphere of nitrogen. Methyl iodide(355 mg, 156 μL, 2.50 mmol) in THF (1 mL) was then added dropwiseover 20 min, and the reaction mixture was stirred under an atmosphereof nitrogen for 5 days. The reaction was quenched with NH4Cl solution(15 mL, 5% w/w), then extracted with ethyl acetate (4×15 mL). Theorganic extracts were dried over MgSO4 and the solvent was removedunder reduced pressure. The residue was purified by silica columnchromatography (EtOAc/hexane 1:19 v/v) to yield product 31 (r.f. 0.50in EtOAc/hexane 1:4 v/v) as a white solid (94 mg, 23%).1H NMR (400 MHz, CD3OD) δ 7.79 (br s, 1H), 7.23 (d, J=8.8 Hz,1H), 7.05 (s, 1H), 6.95 (s, 1H), 6.88 (d, J=8.8 Hz, 1H), 3.90 (s, 3H),2.33 (s, 3H); 13C NMR (101 MHz, CD3OD) δ 154.0, 131.6, 128.7, 122.6,112.2, 111.8, 111.5, 100.8, 56.1, 9.9; HRMS (ESI+) calculated forC10H12NO+ (M+H)+: 162.0913, found: 162.0915.
  • 55
  • [ 21987-25-7 ]
  • [ 696-62-8 ]
  • 5-methoxy-1-(4-methoxyphenyl)-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 120℃; for 16h;
  • 56
  • [ 21987-25-7 ]
  • [ 1185180-71-5 ]
  • 3-(5-methoxy-3-methyl-1H-indol-1-yl)-1-phenylpyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 5-methoxy-3-methyl-1H-indole With mesitylcopper(I) In m-xylene for 0.166667h; Inert atmosphere; Glovebox; Stage #2: With (R)-SITCP In m-xylene for 0.166667h; Inert atmosphere; Glovebox; Stage #3: 3-iodo-1-phenylpyrrolidin-2-one With caesium carbonate In m-xylene at 24 - 25℃; for 72h; Inert atmosphere; Darkness;
  • 57
  • [ 21987-25-7 ]
  • [ 1185180-71-5 ]
  • C20H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 5-methoxy-3-methyl-1H-indole With mesitylcopper(I) In m-xylene for 0.166667h; Inert atmosphere; Glovebox; Stage #2: With C25H23P In m-xylene for 0.166667h; Inert atmosphere; Glovebox; Stage #3: 3-iodo-1-phenylpyrrolidin-2-one With caesium carbonate In m-xylene at 24 - 25℃; for 72h; Inert atmosphere; Darkness;
  • 58
  • [ 21987-25-7 ]
  • [ 7338-94-5 ]
  • 7-methoxy-9-(5-methoxy-3-methyl-1H-indol-2-yl)-9-methyl-1,3-diphenyl-9H-pyrrolo[1,2-a]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With toluene-4-sulfonic acid In dichloromethane at 60℃; for 24h; Sealed tube;
  • 59
  • [ 21987-25-7 ]
  • [ 1135-24-6 ]
  • 1-(4-hydroxy-3-methoxyphenyl)-7-methoxy-9-methyl-1,2-dihydro-1H-pyrrolo[1,2-a]indol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With copper(ll) bromide In acetonitrile at 80℃;
  • 60
  • [ 21987-25-7 ]
  • [ 58028-74-3 ]
  • 13-methoxy-15-methyl-1,2,3,15b-tetrahydro-9H-benzo[5,6]pyrrolo[2',1':3,4][1,4]diazepino[1,2-a]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With 1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; sodium sulfate In dichloromethane at 80℃; for 24h; Sealed tube; regioselective reaction;
  • 61
  • [ 21987-25-7 ]
  • [ 1146-43-6 ]
  • N-(9-methoxy-10b-methyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With hemin; dihydrogen peroxide; sodium hydroxide In water; acetonitrile at 20℃; for 20h;
  • 62
  • [ 21987-25-7 ]
  • [ 66552-44-1 ]
  • ethyl (3aS,8aR)-5-methoxy-1-((methoxycarbonyl)amino)-2,3a-dimethyl-1,3a,8,8atetrahydropyrrolo[2,3-b]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In dichloromethane at 20℃; for 0.5h; Inert atmosphere; enantioselective reaction;
  • 63
  • [ 21987-25-7 ]
  • C14H14N2O [ No CAS ]
  • C24H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With C34H36F6FeN4O6S2 In dichloromethane at -40℃; Molecular sieve; Inert atmosphere; enantioselective reaction;
  • 64
  • [ 2436-17-1 ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: 5-methoxyindole-3-acetonitrile With 15-crown-5; sodium In hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With water In hexane at 0℃; for 1h; 12 Example 12 In a 10 mL single-necked round bottom flask under argon protection, a suspension of sodium dispersion in n-hexane (19.5 wt%, 5.00 mmol) was added, and then hexane (1.0 mL) was added, and 15-crown- 5 (5.00 mmol) and stirred vigorously for 5 min.A solution of 1j (93.1 mg, 0.5 mmol) in hexane (2.0 mL) was added and stirred vigorously at 0 ° C for 20 minutes. H2O (5.00 mmol) was then added. The reaction mixture was stirred vigorously at 0 ° C for 1 hour, and the reaction was quenched with a saturated aqueous sodium bicarbonate solution (2.0 mL). Anhydrous ether was added and the mixture was extracted with saturated sodium chloride solution. The organic phase was dried, concentrated, and separated by column chromatography to obtain 56.4 mg of the target compound 2j in a yield of 70%.
70% Stage #1: 5-methoxyindole-3-acetonitrile With 15-crown-5; sodium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: With water In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; chemoselective reaction;
  • 65
  • [ 21987-25-7 ]
  • [ 106-96-7 ]
  • C13H13NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide; toluene; mineral oil at 0 - 20℃; for 2h; Inert atmosphere;
  • 66
  • [ 21987-25-7 ]
  • [ 100-46-9 ]
  • 3-benzyl-6-methoxyquinazolin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 100℃; for 12h; Schlenk technique; Inert atmosphere;
  • 67
  • [ 21987-25-7 ]
  • [ 10419-77-9 ]
  • C15H22NO4P [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With norborn-2-ene; palladium(II) acetylacetonate; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 36h;
  • 68
  • 5-methoxy-3-methylindoline [ No CAS ]
  • [ 21987-25-7 ]
YieldReaction ConditionsOperation in experiment
92% With monoamine oxidase D11 In aq. phosphate buffer; dimethyl sulfoxide at 37℃; for 168h; Enzymatic reaction;
  • 69
  • [ 21987-25-7 ]
  • [ 32366-02-2 ]
  • N-benzyl-5-methoxy-N,3-dimethyl-1H-indole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% Stage #1: 5-methoxy-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 75℃; for 3h; Stage #2: benzyl(methyl)carbamic chloride In N,N-dimethyl-formamide; mineral oil at 0 - 75℃; for 16h;
  • 70
  • [ 21987-25-7 ]
  • 2-benzylidene-N-tosylbenzofuran-3(2H)-imine [ No CAS ]
  • (S)-N-(2-((5-methoxy-3-methyl-1H-indol-2-yl)(phenyl)methyl)benzofuran-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With C45H31O4P In chloroform at -20℃; for 5h; enantioselective reaction;
  • 71
  • [ 75-91-2 ]
  • [ 21987-25-7 ]
  • [ 105-56-6 ]
  • (Z)-ethyl 2-(3-(tert-butylperoxy)-5-methoxy-3-methylindolin-2-ylidene)-2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With potassium iodide In decane; acetonitrile at 100℃; for 12h; Inert atmosphere;
  • 72
  • [ 21987-25-7 ]
  • C18H21NO3 [ No CAS ]
  • C28H30N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 73
  • [ 21987-25-7 ]
  • 1,1,1-trifluoro-2-(1H-indol-3-yl)-4-(trimethylsilyl)but-3-yn-2-ol [ No CAS ]
  • C25H25F3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 74
  • [ 21987-25-7 ]
  • [ 1417717-41-9 ]
  • C28H21F3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With (R)-2,6-di([1,1'-biphenyl]-4-yl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-oxide In dichloromethane at 20℃;
  • 75
  • [ 21987-25-7 ]
  • C15H15F4NOSi [ No CAS ]
  • C25H24F4N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 76
  • [ 21987-25-7 ]
  • C15H15ClF3NOSi [ No CAS ]
  • C25H24ClF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 77
  • [ 21987-25-7 ]
  • C15H15BrF3NOSi [ No CAS ]
  • C25H24BrF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 78
  • [ 21987-25-7 ]
  • C16H18F3NOSi [ No CAS ]
  • C26H27F3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 79
  • [ 21987-25-7 ]
  • C16H18F3NO2Si [ No CAS ]
  • C26H27F3N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 80
  • [ 21987-25-7 ]
  • C15H15ClF3NOSi [ No CAS ]
  • C25H24ClF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 81
  • [ 21987-25-7 ]
  • C16H18F3NO2Si [ No CAS ]
  • C26H27F3N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 82
  • [ 21987-25-7 ]
  • C15H18F3NOSi [ No CAS ]
  • C25H27F3N2OSi [ No CAS ]
  • C25H27F3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
88 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; Overall yield = 78 percent; enantioselective reaction;
  • 83
  • [ 21987-25-7 ]
  • 1,1,1-trifluoro-2-(1H-indol-3-yl)-5,5-dimethylhex-3-yn-2-ol [ No CAS ]
  • C26H25F3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 84
  • [ 21987-25-7 ]
  • C15H17F4NOSi [ No CAS ]
  • C25H26F4N2OSi [ No CAS ]
  • C25H26F4N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; Overall yield = 85 percent; enantioselective reaction;
  • 85
  • [ 21987-25-7 ]
  • C15H17ClF3NOSi [ No CAS ]
  • C25H26ClF3N2OSi [ No CAS ]
  • C25H26ClF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
86 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; Overall yield = 92 percent; enantioselective reaction;
  • 86
  • [ 21987-25-7 ]
  • C15H17BrF3NOSi [ No CAS ]
  • C25H26BrF3N2OSi [ No CAS ]
  • C25H26BrF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
85 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; Overall yield = 90 percent; enantioselective reaction;
  • 87
  • [ 21987-25-7 ]
  • C16H20F3NOSi [ No CAS ]
  • C26H29F3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 88
  • [ 21987-25-7 ]
  • C16H20F3NO2Si [ No CAS ]
  • C26H29F3N2O2Si [ No CAS ]
  • C26H29F3N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
88 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; Overall yield = 80 percent; enantioselective reaction;
  • 89
  • [ 21987-25-7 ]
  • C15H17F4NOSi [ No CAS ]
  • C25H26F4N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 90
  • [ 21987-25-7 ]
  • C15H17ClF3NOSi [ No CAS ]
  • C25H26ClF3N2OSi [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 91
  • [ 21987-25-7 ]
  • C16H20F3NO2Si [ No CAS ]
  • C26H29F3N2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With C32H11F10O4P; magnesium sulfate In dichloromethane at 20℃; enantioselective reaction;
  • 92
  • [ 21987-25-7 ]
  • C13H12F3NO [ No CAS ]
  • C23H21F3N2O [ No CAS ]
  • C23H21F3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
56 % ee With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; Overall yield = 62 percent; enantioselective reaction;
  • 93
  • [ 21987-25-7 ]
  • C16H15F4NO [ No CAS ]
  • C26H24F4N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 94
  • [ 21987-25-7 ]
  • C16H15BrF3NO [ No CAS ]
  • C26H24BrF3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 95
  • [ 21987-25-7 ]
  • C17H18F3NO [ No CAS ]
  • C27H27F3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 96
  • [ 21987-25-7 ]
  • C17H18F3NO2 [ No CAS ]
  • C27H27F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 97
  • [ 21987-25-7 ]
  • C16H15F4NO [ No CAS ]
  • C26H24F4N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 98
  • [ 21987-25-7 ]
  • C16H15ClF3NO [ No CAS ]
  • C26H24ClF3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 99
  • [ 21987-25-7 ]
  • C17H18F3NO2 [ No CAS ]
  • C27H27F3N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 100
  • [ 21987-25-7 ]
  • C16H15ClF3NO [ No CAS ]
  • C26H24ClF3N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With C32H11F10O4P; magnesium sulfate In dichloromethane at 10℃; enantioselective reaction;
  • 101
  • [ 623-73-4 ]
  • [ 21987-25-7 ]
  • [ 1449683-70-8 ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine In ethanol; water monomer at 20℃; for 12h; Irradiation; Inert atmosphere; 1-3 Preparation method: add 0.1mmol 5-methoxy-3-methylindole, 0.3mmol ethyl 2-diazoacetate, 0.2mmol triethylamine, 10mg g-C3N4 and 2ml solvent (ethanol: Water is 1:1V/V), and stirred at room temperature (20°C) for 12 hours under 400-410nm LED irradiation in an argon atmosphere.After the reaction, the reaction mixture was rotary evaporated to remove water, and then washed with ethyl acetate for several times. Then the obtained washing solution was dried with anhydrous sodium sulfate, filtered, rotary dried, and separated through a silica gel column to obtain a yellow oil. Yield 71%.
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