Home Cart 0 Sign in  
X

[ CAS No. 1219741-50-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 1219741-50-0
Chemical Structure| 1219741-50-0
Chemical Structure| 1219741-50-0
Structure of 1219741-50-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

Quality Control of [ 1219741-50-0 ]

Related Doc. of [ 1219741-50-0 ]

Alternatived Products of [ 1219741-50-0 ]
Product Citations

Product Details of [ 1219741-50-0 ]

CAS No. :1219741-50-0 MDL No. :MFCD09834853
Formula : C9H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :LJFVGMUBSYLFLX-UHFFFAOYSA-N
M.W : 210.07 Pubchem ID :53402958
Synonyms :

Calculated chemistry of [ 1219741-50-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.11
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.96
TPSA : 15.79 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) : -5.38 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.06
Log Po/w (XLOGP3) : 3.1
Log Po/w (WLOGP) : 3.24
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 3.67
Consensus Log Po/w : 2.94

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.7
Solubility : 0.0418 mg/ml ; 0.000199 mol/l
Class : Soluble
Log S (Ali) : -3.1
Solubility : 0.167 mg/ml ; 0.000795 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.53
Solubility : 0.00621 mg/ml ; 0.0000296 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 1219741-50-0 ]

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

Application In Synthesis of [ 1219741-50-0 ]

* 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 [ 1219741-50-0 ]

[ 1219741-50-0 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 1190314-65-8 ]
  • [ 1219741-50-0 ]
YieldReaction ConditionsOperation in experiment
44% With dimethylsulfide borane complex In tetrahydrofuran at 0 - 50℃; for 12h; 105 Intermediate 105 6-bromo-3-methyl-1H-indole To a solution of intermediate 104 (3.0 g, 12.48 mmoles) in THF (120 ml) cooled to 0° C., boron-dimethylsulfide (2M in THF, 62.44 mmoles) was added and heated to 50° C. After 12 h, the reaction mixture was cooled to 0° C., quenched with methanol and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (1.15 g, 44% yield). 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 10.85 (s, 1H), 7.48 (d, J=1.8 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.12 (t, J=1.1 Hz, 1H), 7.09 (dd, J=8.4, 1.8 Hz, 1H), 2.22 (s, 3H).
With dimethylsulfide borane complex In tetrahydrofuran at 60℃; B Step B 6-bromo-3-methyl-1H-indole. A mixture of 6-bromo-3-hydroxy-3-methyl-1,3-dihydro-2H-indol-2-one (0.25 g, 1.0 mmol) and BH3-S(CH3)2 (5.16 mL. 1.0 M, 5.16 mmol) in THF (20 mL) was heated at 60° C. The reaction was quenched with MeOH. Volatiles were removed. Chromatography over silica eluting with 4:1 hexane:EtOAc afforded the title compound. LC-MS: calculated for C9H8BrN 210.07, observed m/e 211.0 (M+H)+ (Rt 1.14 min).
Stage #1: 6-bromo-3-hydroxy-3-methylindolin-2-one With dimethylsulfide borane complex In tetrahydrofuran at 60℃; Stage #2: With methanol In tetrahydrofuran 28.B A mixture of 6-bromo~3-hydroxy-3-methyl-l,3-dihydro- 2/f-indol-2-one (0.25 g, 1.0 mmol) and BH3-S(CHs)2 (5.16 mL. 1.0 M, 5.16 mmol) in THF (20 mL) was heated at 60 0C. The reaction was quenched with MeOH. Volatiles were removed. Chromatography over silica eluting with 4:1 hexane: EtOAc afforded the title compound. LC- MS: calculated for C9H8BrN: 210.07, observed m/e 21 LO (M + H)+ (Rt 1.14 min).
Stage #1: 6-bromo-3-hydroxy-3-methylindolin-2-one With dimethylsulfide borane complex In tetrahydrofuran at 60℃; Stage #2: With methanol In tetrahydrofuran 29.B A mixture of 6-bromo-3-hydroxy-3-methyl-l,3-cu'hydro- 2H-indol-2-one (0.25 g, 1.0 mmol) and BH3-S(CH3)2 (5.16 mL. 1.0 M, 5.16 mmol) in THF (20 mL) was heated at 60 0C. The reaction was quenched with MeOH. Volatiles were removed. Chromatography over silica eluting with 4:1 hexane:EtOAc afforded the title compound. LC- MS: calculated for C9H8BrN: 210.07, observed m/e 21 LO (M + H)+ (Rt 1.14 min).

  • 2
  • [ 1219741-50-0 ]
  • [ 73183-34-3 ]
  • [ 1300582-52-8 ]
YieldReaction ConditionsOperation in experiment
48% With potassium acetate In 1,4-dioxane at 80℃; for 12.5h; Inert atmosphere; 106 Intermediate 106 3-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole To a solution of intermediate 105 (1.10 g, 5.23 mmoles) in Dioxan (33 ml), bis(pinacaloto)diboron (1.60 g, 6.28 mmoles) and potassium acetate (1.54 g, 15.70 mmoles) were added and the system is degassed for 30 min Bis(diphenylphosphinoferrocene)dichloro palladium.CH2Cl2 (0.128 g, 0.157 mmoles) was added under nitrogen atmosphere and heated to 80° C. After 12 h, the reaction mixture filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (0.651 g, 48% yield).). 1H-NMR (δ ppm, DMSO-d6, 400 MHz): δ 10.81 (s, 1H), 7.68 (s, 1H), 7.45 (d, J=7.9 Hz, 1H),), 7.28 (d, J=7.9 Hz, 1H), 7.19 (s, 1H), 2.23 (s, 3H), 1.28 (s, 12H).
  • 3
  • [ 6326-79-0 ]
  • [ 1219741-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 12 h / 20 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 12 h / 0 - 50 °C
  • 4
  • [ 1219741-50-0 ]
  • [ 1300585-21-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 12.5 h / 80 °C / Inert atmosphere 2: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; ethanol; water / 12.5 h / 80 °C / Inert atmosphere
  • 5
  • [ 1219741-50-0 ]
  • C31H24N6O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 12.5 h / 80 °C / Inert atmosphere 2: sodium carbonate / N,N-dimethyl-formamide; ethanol; water / 12.5 h / 80 °C / Inert atmosphere
  • 6
  • [ 1219741-50-0 ]
  • [ 74-88-4 ]
  • [ 1616099-24-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 4h; 3 Step 3: 6-Bro -l,3-dimethyl-lH-indole To a solution of 6-bromo-3-methyl- lH-indole (200 mg, 0.95 mmol) in DMF (8 mL) was added NaH (114 mg, 2.85 mmol, m /60 ). The mixture was stirred at room temperature for lh before the addition of Mel (162 mg, 1.14 mmol). The system was stirred at room temperature for 4h then the mixture was quenched with water and extracted with EtOAc. The organic layer was concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 224.1 [M+H]+.
Stage #1: 6-bromo-3-methyl-1H-indole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 2h; 6-Bromo-1 ,3-dimethyl-1H-indole To an ice-cooled solution of 6-bromo-3-methylindole (1.00 g, 4.76 mmol) in DMF (20 mL), NaH (60% in oil, 381 mg, 9.52 mmol) is added, and the mixture is stirred at 0 °C for 30 min. Mel (0.449 mL, 7.14 mmol) is added, and the mixture is stirred at rt for 2 h. The mixture is diluted with water (100 mL) and EtOAc (100 mL). The layers are separated. The aq. phase is extracted with EtOAc (2x 50 mL). The comb. org. layers are washed with water and brine, dried over MgSC^, filtered, and the solvents are removed under reduced pressure to yield the crude title product. LC-MS: tR = 0.95 min (conditions 3).
  • 7
  • [ 52415-29-9 ]
  • [ 1219741-50-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: trichlorophosphate / 0.5 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: lithium aluminium hydride / tetrahydrofuran / 4 h / 0 - 70 °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 / 20 °C
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
  • 8
  • [ 17826-04-9 ]
  • [ 1219741-50-0 ]
YieldReaction ConditionsOperation in experiment
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 70℃; for 4h; To a solution of 6-bromo-lH-indole-3-carbaldehyde (300 mg, 1.34 mmol) in THF (10 mL) was added L1AIH4 (100 mg, 2.63 mmol) at 0 C. The mixture was heated to 70 C and stirred for 4h at this temperature. Upon cooling, the reaction solution was quenched with 40% of NaOH and filtered and the filtrate concentrated to give crude product which was used in next step without further purification. LCMS (m/z): 210.1 [M+H]+.
  • 9
  • [ 1219741-50-0 ]
  • [ 1616097-59-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C 1.2: 4 h / 20 °C 2.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 16 h / 100 °C / Inert atmosphere
  • 10
  • [ 1219741-50-0 ]
  • N-(4,4-dimethoxycyclohexa-2,5-dien-1-ylidene)-4-methylbenzenesulfonamide [ No CAS ]
  • C23H21BrN2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With zinc trifluoromethanesulfonate In toluene at 25℃; for 24h;
  • 11
  • [ 1219741-50-0 ]
  • [ 37051-70-0 ]
  • N-((5aR,10bS)-8-bromo-10b-methyl-6,10b-dihydro-5aH-benzofuro[2,3-b]indol-2-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid In acetonitrile at 0℃; for 5h; enantioselective reaction;
  • 12
  • C9H9Br2N [ No CAS ]
  • [ 1219741-50-0 ]
YieldReaction ConditionsOperation in experiment
59% With tetrabutylammomium bromide; potassium acetate; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;
  • 13
  • [ 1219741-50-0 ]
  • ethyl 4-phenyl-2-oxobut-3-enoate [ No CAS ]
  • ethyl 6-bromo-9-methyl-1-phenyl-9H-pyrrolo[1,2-a]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 4h;
  • 14
  • [ 1375649-39-0 ]
  • [ 1219741-50-0 ]
  • ethyl 6-bromo-9-methyl-1-p-tolyl-9H-pyrrolo[1,2-a]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 4h;
  • 15
  • [ 1219741-50-0 ]
  • ethyl 2-oxo-4-(p-methoxyphenyl)but-3-enoate [ No CAS ]
  • ethyl 6-bromo-1-(4-methoxyphenyl)-9-methyl-9H-pyrrolo[1,2-a]-indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 4h;
  • 16
  • [ 133678-11-2 ]
  • [ 1219741-50-0 ]
  • ethyl 6-bromo-1-(4-chlorophenyl)-9-methyl-9H-pyrolo[1,2-a]indole-3-carboylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 4h;
  • 17
  • [ 1219741-50-0 ]
  • ethyl 2-oxo-4-(2-thienyl)butenoate [ No CAS ]
  • ethyl 6-bromo-9-methyl-1-(thiophen-2-yl)-9H-pyrrolo[1,2-a]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 6.5h;
  • 18
  • [ 1219741-50-0 ]
  • C16H16FeO3 [ No CAS ]
  • ethyl 6-bromo-1-ferrocenyl-9-methyl-9H-pyrrolo[1,2-a]indole-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With copper(II) bis(trifluoromethanesulfonate) In 1,4-dioxane at 70℃; for 5h;
  • 19
  • [ 97-94-9 ]
  • [ 1219741-50-0 ]
  • C15H22BBrN(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-3-methyl-1H-indole With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: triethyl borane In tetrahydrofuran for 0.25h; Inert atmosphere;
  • 20
  • [ 1219741-50-0 ]
  • C14H13NO4 [ No CAS ]
  • ethyl (3S,3'R)-6'-bromo-3'-(6-bromo-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
92% 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 7h; Inert atmosphere; stereoselective reaction;
  • 21
  • [ 144252-22-2 ]
  • [ 1219741-50-0 ]
  • (S)-3-(6-bromo-3-methyl-1H-indol-1-yl)-3-phenylisoindolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With C35H35O4P In 1,2-dichloro-ethane at 20℃; for 12h; Molecular sieve; enantioselective reaction;
  • 22
  • [ 1219741-50-0 ]
  • [ 956-92-3 ]
  • (S)-3-(6-bromo-3-methyl-1H-indol-1-yl)-3-(4-chlorophenyl)isoindolin-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With C35H35O4P In 1,2-dichloro-ethane at 20℃; for 12h; Molecular sieve; enantioselective reaction;
  • 23
  • [ 24424-99-5 ]
  • [ 1219741-50-0 ]
  • tert-butyl 6-bromo-3-methylindole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 20℃; General procedure i: Synthesis of methyl 3-[(6-bromoindol-1-yl)methyl]benzoate (7a). General procedure: 458 mg (2.0 mmol) of methyl 3-(bromomethyl) benzoate (6a) and 382 mg (2.0 mmol) 6-bromoindole (5a) were added into a 50 mL flask, then 5.0 mL anhydrous DMF and 1.38 g (10.0mmol) potassium carbonate were added. The mixture was stirred at room temperature overnight.TLC indicated no starting material remained and the reaction was quenched by adding 25 mLwater. The solution was extracted with ethyl acetate (30 mL ×3) or dichloromethane (30 mL ×3).The organic solvent was combined and evaporated, the product was purified by flash column chromatography using hexane : ethyl acetate (7:1) as eluent. 655.2 mg target compound obtainedas pale yellow oil, yield 95%.
  • 24
  • [ 1219741-50-0 ]
  • C31H30N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2.1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C 3.2: 20 °C
  • 25
  • [ 1219741-50-0 ]
  • tert-butyl 6-(1H-indol-6-yl)-3-methylindole-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere
  • 26
  • [ 1219741-50-0 ]
  • 3-[[6-(1-tert-butoxycarbonyl-3-methylindol-6-yl)indol-1-yl]methyl]benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2.1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C 3.2: 20 °C 4.1: sodium hydroxide / water / 0.5 h
  • 27
  • [ 625-34-3 ]
  • [ 1219741-50-0 ]
  • 1,1'-(3-bromo-11-methyl-6-(2-oxopropyl)-6H-azepino[1,2-a]indole-7,9-diyl)bis(ethan-1-one) [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With C38H34P2Se2(2+)*2Cl4Ga(1-); sodium sulfate; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In dichloromethane at 0℃; Inert atmosphere;
  • 28
  • [ 1219741-50-0 ]
  • [ 2926-29-6 ]
  • 6-Bromo-3-methyl-2-(trifluoromethyl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With mesoporous graphitic carbon nitride In dimethyl sulfoxide at 25℃; Irradiation;
  • 29
  • [ 1219741-50-0 ]
  • [ 7338-94-5 ]
  • 6-bromo-9-(6-bromo-3-methyl-1H-indol-2-yl)-9-methyl-1,3-diphenyl-9H-pyrrolo[1,2-a]indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With toluene-4-sulfonic acid In dichloromethane at 60℃; for 24h; Sealed tube;
  • 30
  • [ 1219741-50-0 ]
  • [ 106-96-7 ]
  • C12H10BrN [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: 6-bromo-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;
  • 31
  • [ 1219741-50-0 ]
  • C19H14BrF6NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: zinc dibromide; dirhodium tetraacetate / 2 h / 90 °C / Inert atmosphere
  • 32
  • [ 1219741-50-0 ]
  • N-(4-(2-hydroxy-4-phenylbut-3-yn-2-yl)phenyl)acetamide [ No CAS ]
  • (S)-N-(4-(6-bromo-3,9-dimethyl-1-phenyl-3H-pyrrolo[1,2-a]indol-3-yl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With 4-fluoroboronic acid; (S)-3,3'-bis(2,4,6-triisopropylphenyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In chloroform at 20℃; for 48h; Molecular sieve; enantioselective reaction;
  • 33
  • [ 1219741-50-0 ]
  • 2-benzylidene-N-tosylbenzofuran-3(2H)-imine [ No CAS ]
  • (S)-N-(2-((6-bromo-3-methyl-1H-indol-2-yl)(phenyl)methyl)benzofuran-3-yl)-4-methylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With (Ra)-4-hydroxy-2,6-bis(2,4,6-triisopropylphenyl)-5,5’,6,6’,7,7’,8,8’-octahydrodinaphtho[1,3,2]dioxaphosphepine 4-oxide In 1,1,1-trichloroethane at 20℃; for 12h; Molecular sieve; enantioselective reaction;
  • 34
  • [ 1219741-50-0 ]
  • 1-bromo-2,4-diphenylbut-3-yn-2-ol [ No CAS ]
  • C17H14BrNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 6-bromo-3-methyl-1H-indole With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h; Inert atmosphere; Stage #2: 1-bromo-2,4-diphenylbut-3-yn-2-ol In dimethyl sulfoxide at 20℃; Inert atmosphere;
  • 35
  • [ 1219741-50-0 ]
  • (E)-2-(6-bromo-3-methyl-1H-indol-1-yl)-1-phenylethan-1-one O-acetyl oxime [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride / ethanol / 20 °C / Molecular sieve 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C
  • 36
  • [ 1219741-50-0 ]
  • C17H15BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / dimethyl sulfoxide / 2 h / 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: hydroxylamine hydrochloride / ethanol / 20 °C / Molecular sieve
  • 37
  • [ 1219741-50-0 ]
  • [ 201286-69-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 16 h / 120 °C 2: sodium hydroxide; methanol; water / 16 h / 20 °C
  • 38
  • [ 67-56-1 ]
  • [ 201230-82-2 ]
  • [ 1219741-50-0 ]
  • [ 184151-49-3 ]
YieldReaction ConditionsOperation in experiment
77.72% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine at 120℃; for 16h; 2 Step 2. Into a 50-mL round-bottom flask, was placed 6-bromo-3-methyl-1H-indole (1.00 g, 4.760 mmol, 1.00 equiv), MeOH (10.00 mL), TEA (1445.06 mg, 14.281 mmol, 3.00 equiv), Pd(dppf)Cl2(174.15 mg, 0.238 mmol, 0.05 equiv), CO . The resulting solution was stirred for 16 hr at 120 °C. The solids were filtered out. The resulting mixture was concentrated. This resulted in 700 mg (77.72%) of methyl 3-methyl-1H-indole-6-carboxylate as a brown solid. LCMS: [M+1]+=190.
  • 39
  • [ 75-91-2 ]
  • [ 1219741-50-0 ]
  • [ 105-56-6 ]
  • (Z)-ethyl 2-(6-bromo-3-(tert-butylperoxy)-3-methylindolin-2-ylidene)-2-cyanoacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With potassium iodide In decane; acetonitrile at 100℃; for 12h; Inert atmosphere;
  • 40
  • [ 109-04-6 ]
  • [ 1219741-50-0 ]
  • C14H11BrN2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With potassium hydroxide In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 41
  • [ 109-04-6 ]
  • [ 1219741-50-0 ]
  • C24H17BrN2O [ No CAS ]
  • C24H17BrN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide / dimethyl sulfoxide / 24 h / 120 °C / Inert atmosphere 2: dichloro(benzene)ruthenium(II) dimer; silver(I) nitrate / 1,2-dichloro-ethane / 48 h / 25 °C / Sealed tube
  • 42
  • [ 1219741-50-0 ]
  • [ 685-87-0 ]
  • diethyl 2-(6-bromo-3-methyl-1H-indol-2-yl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With N,N-diphenyl-4-methoxyaniline In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere; Irradiation;
  • 43
  • [ 497957-17-2 ]
  • [ 1219741-50-0 ]
  • 1-(4-(5-((6-bromo-3-methyl-1H-indol-1-yl)sulfonyl)-2-methoxyphenyl)piperazin-1-yl)-2,2,2-trifluoroethanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With benzyl-triethyl-ammonium chloride; potassium hydroxide In dichloromethane; lithium hydroxide monohydrate at 25℃; for 4h; 4.1.4 General procedure for preparation of intermediates 5a-5i and 7a-7f. General procedure: To a mixture of corresponding indole derivatives 4 or 6 (3.0mmol, 1.0 equiv), intermediate 3 (4.5mmol, 1.5 equiv) and benzyltriethylammonium chloride (0.6mmol, 0.2 equiv) in dichloromethane (10mL) was added a solution of potassium hydroxide (6.0mmol, 2.0 equiv) in water (2mL). The reaction mixture was stirred at room temperature for 4h. Water (10mL) was added, the organic layer was collected, dried over anhydrous Na2SO4 and concentrated in vacuum. The crude product was purified by column chromatography on silica gel using (PE/EA=2:1 (v:v)) as solvent to give intermediates 5a-5i or 7a-7f.
  • 44
  • [ 1219741-50-0 ]
  • 4-[2-(2,6-dimethyl-4-pyridyl)-3-methyl-1H-indol-6-yl] benzene-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: iodine; trifluoromethane sulfonic acid silver salt / tetrahydrofuran / 0.5 h / 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / acetonitrile; lithium hydroxide monohydrate / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation 3: chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II); Cs2CO3 / lithium hydroxide monohydrate; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube 4: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 5 h
  • 45
  • [ 1219741-50-0 ]
  • tert-butyl (1S,3R,4R)-3-[6-[2-(2,6-dimethyl-4-pyridyl)-3-methyl-1H-indol-6-yl]-1H-benzimidazol-2-yl]-2-azabicyclo[2.2.1]heptane-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: iodine; trifluoromethane sulfonic acid silver salt / tetrahydrofuran / 0.5 h / 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / acetonitrile; lithium hydroxide monohydrate / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation 3: chloro(2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl)(2′-amino-1,1′-biphenyl-2-yl) palladium(II); Cs2CO3 / lithium hydroxide monohydrate; 1,4-dioxane / 2 h / 110 °C / Inert atmosphere; Sealed tube 4: palladium 10% on activated carbon; hydrogen / ethanol; ethyl acetate / 5 h 5: N-ethyl-N,N-diisopropylamine; O-(7-azabenzotriazol-1-yl)-n,n,n',n'-tetramethyluronium hexafluoro-phosphate / tetrahydrofuran / 1 h
  • 46
  • [ 1219741-50-0 ]
  • C25H27N5*2C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: iodine; trifluoromethane sulfonic acid silver salt / tetrahydrofuran / 0.5 h / 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / acetonitrile; lithium hydroxide monohydrate / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation 3: anhydrous potassium acetate; anhydrous sodium carbonate; Pd[t-Bu2P(4-NMe2C6H4)]2Cl2 / acetonitrile; lithium hydroxide monohydrate / 0.33 h / 140 °C / Inert atmosphere; Microwave irradiation 4: acetonitrile / 0.75 h / 45 °C
  • 47
  • [ 1219741-50-0 ]
  • C26H29N5*2C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: iodine; trifluoromethane sulfonic acid silver salt / tetrahydrofuran / 0.5 h / 20 °C 2: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous potassium acetate / acetonitrile; lithium hydroxide monohydrate / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation 3: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; anhydrous sodium carbonate / lithium hydroxide monohydrate; ethylene glycol dimethyl ether / 2 h / 100 °C / Inert atmosphere; Sealed tube 4: triethylamine / dimethyl sulfoxide / 2 h / 150 °C / Microwave irradiation 5: acetonitrile / 45 °C
  • 48
  • [ 1219741-50-0 ]
  • tert-butyl 4-(5-(2-bromo-3-methyl-1H-indol-6-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: anhydrous potassium acetate; anhydrous sodium carbonate; Pd[t-Bu2P(4-NMe2C6H4)]2Cl2 / acetonitrile; lithium hydroxide monohydrate / 0.5 h / 130 °C / Inert atmosphere; Microwave irradiation 2: pyridinium hydrobromide perbromide / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C
  • 49
  • [ 1219741-50-0 ]
  • 6-bromo-2-iodo-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With iodine; trifluoromethane sulfonic acid silver salt In tetrahydrofuran at 20℃; for 0.5h; 6-bromo-2-iodo-3-methyl-1H-indole To a solution of 6-bromo-3-methyl-1H- indole (2.00 g, 9.52 mmol) in THF (40 mL) was added iodine (2.42 g, 9.52 mmol) and silver trifluoromethanesulfonate (2.94 g, 11.4 mmol) and the reaction mixture was stirred for 30 min at room temperature. The reaction was quenched by the addition of 10% aqueous thiosulfate and the mixture was extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (0-30% EtOAc in hexane) to give I-1 which was carried forward to the next step. ES/MS: 337.1 (M+H+). 1 H NMR (400 MHz, Chloroform-d) δ 7.93 (s, 1H), 7.46 (d, J = 1.7 Hz, 1H), 7.37 (d, J = 8.4 Hz, 1H), 7.22 (dd, J = 8.4, 1.7 Hz, 1H), 2.28 (s, 3H).
With iodine; trifluoromethane sulfonic acid silver salt In tetrahydrofuran at 20℃; for 0.5h; Preparation of Intermediate I-1 6-bromo-2-iodo-3-methyl-1H-indole: To a solution of 6-bromo-3-methyl-1H- indole (2.00 g, 9.52 mmol) in THF (40 mL) was added iodine (2.42 g, 9.52 mmol) and silver trifluoromethanesulfonate (2.94 g, 11.4 mmol) and the reaction mixture was stirred for 30 min at room temperature. The reaction was quenched by the addition of 10% aqueous thiosulfate and the mixture was extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (0-30% EtOAc in hexane) to give I-1 which was carried forward to the next step. ES/MS: 337.1 (M+H+).1H NMR (400 MHz, Chloroform-d) δ 7.93 (s, 1H), 7.46 (d, J = 1.7 Hz, 1H), 7.37 (d, J = 8.4 Hz, 1H), 7.22 (dd, J = 8.4, 1.7 Hz, 1H), 2.28 (s, 3H).
With iodine; trifluoromethane sulfonic acid silver salt In tetrahydrofuran at 20℃; for 0.5h; 6-bromo-2-iodo-3-methyl-1H-indole To a solution of 6-bromo-3-methyl-1H- indole (2.00 g, 9.52 mmol) in THF (40 mL) was added iodine (2.42 g, 9.52 mmol) and silver trifluoromethanesulfonate (2.94 g, 11.4 mmol) and the reaction mixture was stirred for 30 min at room temperature. The reaction was quenched by the addition of 10% aqueous thiosulfate and the mixture was extracted with EtOAc (3x). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by column chromatography (0-30% EtOAc in hexane) to give I-1 which was carried forward to the next step. ES/MS: 337.1 (M+H+). 1 H NMR (400 MHz, Chloroform-d) δ 7.93 (s, 1H), 7.46 (d, J = 1.7 Hz, 1H), 7.37 (d, J = 8.4 Hz, 1H), 7.22 (dd, J = 8.4, 1.7 Hz, 1H), 2.28 (s, 3H).
  • 50
  • [ 496786-98-2 ]
  • [ 1219741-50-0 ]
  • tert-butyl 4-(5-(3-methyl-1H-indol-6-yl)pyridin-2-yl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Pd[t-Bu2P(4-NMe2C6H4)]2Cl2; anhydrous potassium acetate; anhydrous sodium carbonate In lithium hydroxide monohydrate; acetonitrile at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation; tert-butyl 4-(5-(3-methyl-1H-indol-6-yl)pyridin-2-yl)piperazine-1- carboxylate To a vial was added 6-bromo-3-methyl-1H-indole (400 mg, 1.90 mmol), tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (890 mg, 2.28 mmol) and Pd(AmPhos)2Cl2 (0.108 g, 0.15 mmol) followed by acetonitrile (2.0 mL) and 1.0 M potassium acetate/1.5 M sodium carbonate in water (4.8 mL, 4.8 mmol / 7.2 mmol). Nitrogen was bubbled through the reaction mixture for 3 min and the reaction was heated to 130 °C in a microwave for 30 min. The reaction mixture was filtered through celite, eluting with DCM, water was added to the filtrate, the layers were separated, and the aqueous layer was back extracted with DCM (2x). The combined organic layers were combined, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (0-100% EtOAc in hexane) to give the title compound. ES/MS: 393.3 (M+H+).
With Pd[t-Bu2P(4-NMe2C6H4)]2Cl2; anhydrous potassium acetate; anhydrous sodium carbonate In lithium hydroxide monohydrate; acetonitrile at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation; tert-butyl 4-(5-(3-methyl-1H-indol-6-yl)pyridin-2-yl)piperazine-1- carboxylate To a vial was added 6-bromo-3-methyl-1H-indole (400 mg, 1.90 mmol), tert-butyl 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridyl]piperazine-1-carboxylate (890 mg, 2.28 mmol) and Pd(AmPhos)2Cl2 (0.108 g, 0.15 mmol) followed by acetonitrile (2.0 mL) and 1.0 M potassium acetate/1.5 M sodium carbonate in water (4.8 mL, 4.8 mmol / 7.2 mmol). Nitrogen was bubbled through the reaction mixture for 3 min and the reaction was heated to 130 °C in a microwave for 30 min. The reaction mixture was filtered through celite, eluting with DCM, water was added to the filtrate, the layers were separated, and the aqueous layer was back extracted with DCM (2x). The combined organic layers were combined, dried over sodium sulfate, filtered and the filtrate was concentrated in vacuo. The crude residue was purified by column chromatography (0-100% EtOAc in hexane) to give the title compound. ES/MS: 393.3 (M+H+).
  • 51
  • [ 846548-44-5 ]
  • [ 1219741-50-0 ]
  • 6-(2,6-dimethyl-4-pyridyl)-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [2-(2-aminophenyl)phenyl]-chloro-palladium-dicyclohexyl-[3-(2,4,6-triisopropylphenyl)phenyl]phosphane; Cs2CO3 In 1,4-dioxane; lithium hydroxide monohydrate at 110℃; for 2h; Inert atmosphere; Preparation of Intermediate I-5 6-(2,6-dimethyl-4-pyridyl)-3-methyl-1H-indole: To 250 ml RBF was added 6- bromo-3-methyl-1H-indole (4.00 g, 19.0 mmol), 2,6-dimethyl-4-pyridyl)boronic acid (3.20 g, 20.9 mmol), XPhos Pd G2 (748 mg, 0.95 mmol), 10:1 dioxane and water (100 ml) and cesium carbonate (15.50 g, 47.6 mmol). The solution was degassed by bubbling argon for 30 seconds, then heated at 110 °C for 2 hours. The reaction mixture was cooled, filtered through Celite (eluent: EtOAc), and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: EtOAc / Hex) to provide the desired product. ES/MS: 237.2 (M+H+).
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 1219741-50-0 ]

Bromides

Chemical Structure| 10075-48-6

[ 10075-48-6 ]

5-Bromo-3-methyl-1H-indole

Similarity: 0.97

Chemical Structure| 475039-81-7

[ 475039-81-7 ]

4-Bromo-3-methyl-1H-indole

Similarity: 0.95

Chemical Structure| 69902-42-7

[ 69902-42-7 ]

6-Bromo-1,4-dimethyl-9H-carbazole

Similarity: 0.95

Chemical Structure| 936092-87-4

[ 936092-87-4 ]

4-Bromo-7-methyl-1H-indole

Similarity: 0.90

Chemical Structure| 885520-51-4

[ 885520-51-4 ]

6-Bromo-4-methyl-1H-indole

Similarity: 0.90

Related Parent Nucleus of
[ 1219741-50-0 ]

Indoles

Chemical Structure| 10075-48-6

[ 10075-48-6 ]

5-Bromo-3-methyl-1H-indole

Similarity: 0.97

Chemical Structure| 475039-81-7

[ 475039-81-7 ]

4-Bromo-3-methyl-1H-indole

Similarity: 0.95

Chemical Structure| 936092-87-4

[ 936092-87-4 ]

4-Bromo-7-methyl-1H-indole

Similarity: 0.90

Chemical Structure| 885520-51-4

[ 885520-51-4 ]

6-Bromo-4-methyl-1H-indole

Similarity: 0.90

Chemical Structure| 887581-34-2

[ 887581-34-2 ]

(6-Bromo-1H-indol-3-yl)methanamine

Similarity: 0.88