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[ CAS No. 1029720-65-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1029720-65-7
Chemical Structure| 1029720-65-7
Chemical Structure| 1029720-65-7
Structure of 1029720-65-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1029720-65-7 ]

CAS No. :1029720-65-7 MDL No. :MFCD11044699
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :GPICPAIKTJPYEE-UHFFFAOYSA-N
M.W :242.50 Pubchem ID :51341980
Synonyms :

Calculated chemistry of [ 1029720-65-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.45
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 3.75
Log Po/w (WLOGP) : 3.65
Log Po/w (MLOGP) : 2.85
Log Po/w (SILICOS-IT) : 3.76
Consensus Log Po/w : 3.27

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.32
Solubility : 0.0115 mg/ml ; 0.0000476 mol/l
Class : Moderately soluble
Log S (Ali) : -3.71
Solubility : 0.0469 mg/ml ; 0.000194 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.17
Solubility : 0.00162 mg/ml ; 0.00000668 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.52

Safety of [ 1029720-65-7 ]

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

Application In Synthesis of [ 1029720-65-7 ]

* 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 [ 1029720-65-7 ]

[ 1029720-65-7 ] Synthesis Path-Downstream   1~48

  • 1
  • [ 1007882-12-3 ]
  • [ 1029720-65-7 ]
  • [ 1261072-08-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane; water at 120℃; for 0.333333h; sealed vial; Microwave irradiation; 51 7-Bromo-3-chloro-isoquinoline (50 mg, 0.210mmol), (S)-tert-butyl 2-(5-(4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaboro lan-2-yl)phenyl)-1H-imidazol-2-yl)pyrrolidine-1 -carboxylate (108 mg, 0.247mmol), obtained from Preparation 16, and Pd(ddpf)CI2 (17 mg, 0.021 mmol) were dissolved in DME (1 ml_) in a microwave vial. 2M Na2CO3 (aq) (0.309 ml_, 0.618mmol) was then added and the vial was sealed and heated at 1200C for 20 minutes in the microwave. The reaction mixture was then diluted with ethyl acetate (20 ml_) and washed with water (10 ml_) followed by brine (10 ml_). The organic extracts were concentrated in vacuo to give the crude product, which was dry loaded onto silica. Purification by column chromatography on silica gel (redisep 4g, 30:70 to 70:30 EtOAc: Heptane) gave 95 mg of the title compound as a brown glass.1H NMR (CDCI3, 400MHz): δ= 9.12 (s, 1 H), 8.16 (s, 1 H), 8.00 (d, 1 H), 7.84 (d, 1 H), 7.81-7.71 (m, 5H), 5.04 (m, 1 H), 3.47 (m, 2H), 3.02 (m, 1 H), 2.22 (m, 2H), 2.05-1.96 (m, 2H), 1.25 (s, 9H). LCMS (run time = 2 min): R4 = 1.42 min; m/z 475; 477 [M+H]+
  • 2
  • [ 1029720-65-7 ]
  • [ 1261071-80-0 ]
  • [ 1261072-18-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane at 120℃; for 1h; microwave irradiation; sealed; 64 7-Bromo-3-chloroisoquinoline (0.6 g, 2.5 mmol), (2-[(2S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl]-1-[2(trimethylsilyl)ethoxy]methyl}-1H-imidazol-5-yl)boronic acid (0.68 g, 1.5 mmol), obtained from Preparation 13b, and Pd(dppf)CI2.DCM (0.2 g, 0.25 mmol) were added to a microwave vial. The reaction mixture was dissolved in dimethoxyethane (6 mL) and 2M sodium carbonate solution (1.9 mL) was added. The reaction vessel was sealed and heated under microwave radiation at 1200C for 1 hour. Dichloromethane (40 mL) was added to the reaction mixture and it was filtered through Arbocel, which was washed with more dichloromethane (80 mL). The solvent was evaporated and the crude product was purified by column chromatography on silica gel (ethyl acetate: heptane 2:3 to 3:2) to give the title compound as a yellow gum (750 mg).LCMS (run time = 4.5 min): R4 = 3.11 min; m/z 529; 531 [M+H]+
  • 3
  • [ 1029720-65-7 ]
  • [ 124-41-4 ]
  • [ 1246549-59-6 ]
YieldReaction ConditionsOperation in experiment
85% In diethylene glycol dimethyl ether at 150℃; for 1h; 36.1 A mixture of 7-bromo-3-chloroisoquinoline (100 mg, 0.4 mmol) and sodium methoxide (113 mg, 2.1 mmol) in diglyme (1 mL) was heated to 150° C. for 1 hour. The reaction was cooled to room temperature and diluted with toluene and water. The layers were separated and the aqueous layer was extracted with toluene (3×). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to an oil. The oil was dried under vacuum overnight to give the title compound (83 mg, 85%) as a yellow solid. +ESI (M+H+1) 240.1; 1H NMR (400 MHz, CDCl3, δ): 8.87 (s, 1H), 8.01-8.05 (m, 1H), 7.58-7.64 (m, 1H), 7.53-7.58 (m, 1H), 6.97 (s, 1H), 4.02 (s, 3H).
  • 4
  • [ 1029720-65-7 ]
  • [ 593-51-1 ]
  • [ 1374258-76-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In diethylene glycol dimethyl ether at 150℃; for 100h; 41.1 A mixture of 7-bromo-3-chloroisoquinoline (100 mg, 0.4 mmol), methylamine hydrochloride (139 mg, 2.06 mmol), and potassium carbonate (456 mg, 3.30 mmol) in 1-methoxy-2-(2-methoxyethoxy)ethane (1 mL) was heated to 150° C. and stirred for 60 hours. Additional methylamine hydrochloride (100 mg, 1.5 mmol) and potassium carbonate (200 mg, 1.4 mmol) were added and heating was continued for another 40 hours. The reaction was cooled to room temperature and diluted with water. The mixture was stirred for 30 minutes. The resulting solid was filtered off, rinsed with water and dried under vacuum. Purification by flash column chromatography (10-30% ethyl acetate/heptanes) gave the title compound (82 mg) as a pale yellow solid. -APCI (M-H+1) 237.8; 1H NMR (400 MHz, CDCl3, δ): 8.70 (s, 1H), 7.84 (d, J=1.95 Hz, 1H), 7.48 (dd, J=8.97, 2.15 Hz, 1H), 7.38 (d, J=8.97 Hz, 1H), 6.39 (s, 1H), 2.92 (s, 3H).
  • 5
  • [ 1029720-65-7 ]
  • copper(l) cyanide [ No CAS ]
  • [ 1337881-31-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 150℃; for 24h; Inert atmosphere; 6.A Step A: 3-Chloroisoquinoline-7-carbonitrile Step A: 3-Chloroisoquinoline-7-carbonitrile: To a flask charged with 7-bromo-3- chloroisoquinoline (l.Og, 4.1 mmol) and a stir bar was added copper(I) cyanide (550mg, 6.2 mmol) and DMF (50 mL). The mixture was heated to 150 °C for 24 hours under an atmosphere of nitrogen. The reaction was diluted with EtOAc, washed with sat. NH4OAc and brine, dried over sodium sulfate, concentrated and purified by silica gel chromatography (Hexanes:DCM) and the solvent removed to afford the title compound. LC-MS (IE, m/z): 189 [M + 1]+.
  • 6
  • [ 1029720-65-7 ]
  • [ 1431869-46-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane 4: ethanol / 1.5 h / 145 °C / Microwave irradiation
  • 7
  • [ 1029720-65-7 ]
  • 3-{4-[(2R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]-2-oxopiperazin-1-yl}-8-methylquinoline-7-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: N-iodo-succinimide / trifluorormethanesulfonic acid / 20 °C / Cooling with ice 2.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.2: 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.3: 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation 3.1: N,N-dimethyl-formamide / 150 °C 4.1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 0.17 h / 120 °C / Inert atmosphere; Microwave irradiation; Sealed tube
  • 8
  • [ 1029720-65-7 ]
  • [ 1431869-22-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
  • 9
  • [ 1029720-65-7 ]
  • [ 1431869-20-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 24 h / 150 °C / Inert atmosphere 2: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 3: hydrogenchloride / 1,4-dioxane
  • 10
  • [ 1029720-65-7 ]
  • [ 1431869-31-6 ]
YieldReaction ConditionsOperation in experiment
With N-iodo-succinimide In trifluorormethanesulfonic acid at 20℃; Cooling with ice; 12.A Step A: 7-bromo-3-chloro-8-iodoisoquinoline Step A: 7-bromo-3-chloro-8-iodoisoquinolineTo a flask containing 7-Bromo-3-chloroisoquinoline (1.5 g, 6.19 mmol) was added NIS (1.4 g, 6.9 mmol). The flask was placed in an ice bath and treated with TfOH (40 mL) and stirred at RT overnight. The reaction mixture was carefully poured into ice, and the aqueous layer was extracted with DCM. The combined extracts were washed with brine, dried over Na2S04, and concentrated under reduced pressure. The crude residue was purified by silica gel column chromatography (Hexanes:DCM→ 1 : 1) to provide the title product.
  • 11
  • [ 1029720-65-7 ]
  • [ 1431869-32-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: N-iodo-succinimide / trifluorormethanesulfonic acid / 20 °C / Cooling with ice 2.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.2: 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.3: 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation
  • 12
  • [ 1029720-65-7 ]
  • [ 1431869-30-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: N-iodo-succinimide / trifluorormethanesulfonic acid / 20 °C / Cooling with ice 2.1: tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine / 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.2: 0.17 h / 50 °C / Inert atmosphere; Microwave irradiation 2.3: 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation 3.1: N,N-dimethyl-formamide / 150 °C
  • 13
  • [ 1029720-65-7 ]
  • [ 192182-54-0 ]
  • [ 1585145-77-2 ]
YieldReaction ConditionsOperation in experiment
0.5 g With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; sodium carbonate In 1,2-dimethoxyethane; water at 90℃; Sealed tube; Inert atmosphere; 1.1 Step 1.1: 3-chloro-7-(3,5-dimethoxyphenyl) isoquinoline: To a solution of 7-bromo-3-chloroisoquinoline (500 mg, 2.0 mmol) and 3,5- dimethoxyphenylboronic acid (364 mg, 2.0 mmol) in DME and water (1 : 1) in a sealed tube was added S-Phos (42 mg, 5 mole %) followed by Pd(OAc)2 (23 mg, 5 mole %) and disodium carbonate (262 mg, 2.47 mmol). The reaction mixture was purged with Argon, then heated at 90°C for O/N, allowed to cool to room temperature, diluted with EtOAc and water, filtered through a pad of celite and extracted with EtOAc. The organic phase was washed with brine, dried over Na2S04, filtered and concentrated in vacuo. The crude product was purified by Flash chromatography (n-Hexane: EtOAc (9: 1) to afford 0.5 g of the title compound as white solid. 1H NMR (400 MHz, CDC13) δ 9.12 (s, 1H), 8.15 - 8.11 (m, 1H), 7.96 (dd, J = 8.6, 1.8 Hz, 1H), 7.83 (d, J = 8.7 Hz, 1H), 7.75 (s, 1H), 6.82 (d, J = 2.2 Hz, 2H), 6.53 (t, J = 2.2 Hz, 1H), 3.89 (s, 6H). M/Z: 299.7, M+l : 300.3, tR= 3.44 min. (System 2)
  • 14
  • [ 1029720-65-7 ]
  • [ 1585145-45-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: palladium diacetate; XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 90 °C / Inert atmosphere
  • 15
  • [ 1029720-65-7 ]
  • [ 1585145-46-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: palladium diacetate; XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 16
  • [ 1029720-65-7 ]
  • [ 1585145-47-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: palladium diacetate; XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 17
  • [ 1029720-65-7 ]
  • [ 1585145-48-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 18
  • [ 1029720-65-7 ]
  • [ 1585145-78-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C
  • 19
  • [ 1029720-65-7 ]
  • [ 1585145-44-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: palladium diacetate; XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere; Sealed tube
  • 20
  • [ 1029720-65-7 ]
  • [ 1585145-49-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 21
  • [ 1029720-65-7 ]
  • [ 1585145-50-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 22
  • [ 1029720-65-7 ]
  • [ 1585145-51-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 23
  • [ 1029720-65-7 ]
  • [ 1585145-52-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 24
  • [ 1029720-65-7 ]
  • [ 1585145-53-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: sulfuryl dichloride / diethyl ether / 5 - 20 °C 3: tetrakis(triphenylphosphine) palladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 25
  • [ 1029720-65-7 ]
  • [ 1585145-64-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 26
  • [ 1029720-65-7 ]
  • [ 1585145-82-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C
  • 27
  • [ 1029720-65-7 ]
  • [ 1585145-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C
  • 28
  • [ 1029720-65-7 ]
  • [ 1585145-69-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 29
  • [ 1029720-65-7 ]
  • [ 1585145-70-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C 3: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Inert atmosphere
  • 30
  • [ 1029720-65-7 ]
  • [ 1585145-71-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C 3: sulfuryl dichloride / acetonitrile / 1 h / -30 °C 4: tris-(dibenzylideneacetone)dipalladium(0); XPhos; caesium carbonate / toluene; <i>tert</i>-butyl alcohol / 120 °C / Sealed tube; Inert atmosphere
  • 31
  • [ 1029720-65-7 ]
  • [ 1585145-83-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; sodium carbonate; palladium diacetate / 1,2-dimethoxyethane; water / 90 °C / Sealed tube; Inert atmosphere 2: Selectfluor / acetonitrile / 2 h / 20 °C 3: sulfuryl dichloride / acetonitrile / 1 h / -30 °C
  • 32
  • [ 1029720-65-7 ]
  • [ 1445993-89-4 ]
  • 4-(3-chloroisoquinolin-7-yl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.130 g With potassium carbonate In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; 1 4-t3-chloroisoquinolin-7-yQ-6-methyl-l-tosyl-l -pyrrolo[2,3-clpyridin-7t6/ )-one (2) To a stirred solution of Intermediate-5 (0.40 g, 0.8 mmol), 1 (0.22 g, 0.96 mmol), K2CO3 (0.32 g, 2.4 mmol) in dioxane (8.0 mL), water (2.0 mL) was charged at room temperature and degassed it with argon for 5 min at room temperature. Pd(pph3)4 (0.040 g, 0.04 mmol) was added to the reaction mixture and degassed it with argon for 2 min at room temperature. The reaction mixture was heated at 90 °C for 1 h. TLC indicated at which time the reaction had gone to completion. The reaction mixture was diluted with water (25 mL) and extracted with EtOAc (3 x 40 mL). The combined organic layers were dried over anhydrous NaiSCri and concentrated under reduced pressure. The crude product was purified by combi flash chromatography (CH2CI2: CH3OH = 95: 5) to afford 2 (0.130 g) as an off-white solid. NMR (400 MHz, DMSO-): d ppm 9.27 (s, 1H), 8.31 (br.s., 1H), 8.06 - 8.10 (m, 2 H), 7.97 - 8.01 (m, 2 H), 7.82 (s, 1H), 7.59 - 7.64 (m, 1H), 7.53 - 7.57 (m, 1H), 7.44 (d, J= 8.0 Hz, 2 H), 6.88 (d, J= 3.2 Hz, 1H), 3.51 (s, 3 H), 2.39 (s, 3 H).
  • 33
  • [ 1029720-65-7 ]
  • (R)-1,3-dimethyl-4-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}piperazin-2-one [ No CAS ]
  • (R)-4-{2-[4-(3-chloroisoquinolin-7-yl)phenoxy]ethyl}-1,3-dimethylpiperazin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere; 1 To a stirred solution of Intermediate-3 (0.60 g, 01.60 mmol8) in 4: 1 of dioxane, H2O (20 mL), 7-bromo-3-chloroisoquinoline 1 (0.38 g, 1.60 mmol) and KiCCb (0.44 g, 3.20 mmol) were charged at room temperature and purged with argon for 5 min. Pd(dppf)Cl2 (0.11 g, 0.16 mmol) was added followed to the reaction mixture at room temperature. The reaction mixture was heated at 90 °C for 16 h. The reaction mixture was allowed to room temperature and concentrated under reduced pressure. The crude product was purified by combiflash chromatography (CH2CI2: CH3OH = 92: 3) to afford 2 (0.22 g, 33%) as brown colour gum. NMR (400 MHz, CDCb): d ppm d 9.09 (s, 1H), 8.08 (s, 1H), 7.95 (d, J=8.4 Hz, 1H), 7.81 (d, =8.8 Hz, 1H), 7.72 (s, 1H), 7.63 (d, =8.8 Hz, 2 H), 7.03 (d, =8.4 Hz, 2 H).
  • 34
  • [ 1029720-65-7 ]
  • tert-butyl N-(7-formylisoquinolin-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere
  • 35
  • [ 1029720-65-7 ]
  • tert-butyl N-(7-formylisoquinolin-3-yl)-N-methylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere
  • 36
  • [ 1029720-65-7 ]
  • 3-[(tert-butoxycarbonyl)(methyl)amino]isoquinoline-7-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: n-butyllithium / tetrahydrofuran / 1.5 h / -78 - 20 °C / Inert atmosphere 2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 16 h / 100 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere 4: potassium permanganate; potassium hydroxide / water; acetonitrile / 12 h / 20 °C
  • 37
  • [ 1029720-65-7 ]
  • [ 33513-42-7 ]
  • [ 1337879-96-5 ]
YieldReaction ConditionsOperation in experiment
29.11% With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 1.5h; Inert atmosphere; 1 Step 1. Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 7-bromo-3-chloroisoquinoline (1.00 g, 4.124 mmol, 1.00 equiv) in THF (20 mL). This was followed by the addition of n-BuLi (0.58 mL, 6.157 mmol, 1.49 equiv) dropwise with stirring at -78 °C. To this was added DMF (0.60 g, 8.209 mmol, 1.99 equiv) dropwise with stirring at -78 °C. The resulting solution was stirred for 30 min at -78 °C. The resulting solution was allowed to react, with stirring, for an additional 1hr at room temperature. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 3x30 mL of ethyl acetate dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 230 mg (29.11%) of 3-chloroisoquinoline-7- carbaldehyde as a yellow solid. LCMS: [M+H]+=192.
  • 38
  • [ 91-63-4 ]
  • [ 1029720-65-7 ]
  • [ 100-39-0 ]
  • 2-benzyl-7-bromo-1-(quinolin-2-ylmethyl)-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With copper (I) iodide; water monomer; anhydrous Sodium acetate In acetonitrile at 100℃; for 8h; Inert atmosphere; Schlenk technique; 2. Typical procedure for the synthesis of the corresponding products. General procedure: Reagents 2-methylquinolines 1 (0.15 mmol), benzyl bromides 3 (0.225 mmol),3-bromoisoquinolines 2 (0.15 mmol), CuI (5 mol%), NaOAc (0.15 mmol), and 1 mLmixed solvent CH3CN-H2O (6:1) were combined in a 25 mL Schlenk tube and stirredat 100 °C under oil-bath heating for 8 h under N2 atmosphere. After cooling to roomtemperature, the reaction mixture was concentrated by removing the solvent undervacuum. The residue was purified by preparative thin layer chromatography on silica,eluting with petroleum ether (60-90 °C):ethyl acetate (2:1) to give the corresponding products.
  • 39
  • [ 91-63-4 ]
  • [ 1029720-65-7 ]
  • [ 16004-15-2 ]
  • 7-bromo-1-((6-bromoquinolin-2-yl)methyl)-2-(4-iodobenzyl)-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With copper (I) iodide; water monomer; anhydrous Sodium acetate In acetonitrile at 100℃; for 8h; Inert atmosphere; Schlenk technique; 2. Typical procedure for the synthesis of the corresponding products. General procedure: Reagents 2-methylquinolines 1 (0.15 mmol), benzyl bromides 3 (0.225 mmol),3-bromoisoquinolines 2 (0.15 mmol), CuI (5 mol%), NaOAc (0.15 mmol), and 1 mLmixed solvent CH3CN-H2O (6:1) were combined in a 25 mL Schlenk tube and stirredat 100 °C under oil-bath heating for 8 h under N2 atmosphere. After cooling to roomtemperature, the reaction mixture was concentrated by removing the solvent undervacuum. The residue was purified by preparative thin layer chromatography on silica,eluting with petroleum ether (60-90 °C):ethyl acetate (2:1) to give the corresponding products.
  • 40
  • [ 1029720-65-7 ]
  • 3-methylisoquinolin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3: hydrogenchloride / water monomer / 1 h / 20 °C
  • 41
  • [ 1029720-65-7 ]
  • 8-iodo-3-methylisoquinolin-7-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3: hydrogenchloride / water monomer / 1 h / 20 °C 4: glacial acetic acid; Iodine monochloride / 1 h / 20 °C
  • 42
  • [ 1029720-65-7 ]
  • (7-amino-3-methylisoquinolin-8-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3: hydrogenchloride / water monomer / 1 h / 20 °C 4: glacial acetic acid; Iodine monochloride / 1 h / 20 °C 5: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere
  • 43
  • [ 1029720-65-7 ]
  • (7-((5-bromo-2-chloropyrimidin-4-yl)amino)-3-methylisoquinolin-8-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3: hydrogenchloride / water monomer / 1 h / 20 °C 4: glacial acetic acid; Iodine monochloride / 1 h / 20 °C 5: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 6: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 3 h / 0 - 20 °C
  • 44
  • [ 1029720-65-7 ]
  • (7-((5-bromo-2-((5-ethyl-2-methoxy-4-(4-(piperazin-1-yl)piperidin-1-yl)phenyl)amino)pyrimidin-4-yl)amino)-3-methylisoquinolin-8-yl)dimethylphosphine oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3: hydrogenchloride / water monomer / 1 h / 20 °C 4: glacial acetic acid; Iodine monochloride / 1 h / 20 °C 5: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 6: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 3 h / 0 - 20 °C 7: toluene-4-sulfonic acid / butan-1-ol / 13 h / 100 °C
  • 45
  • [ 1029720-65-7 ]
  • 3-(4-(2-(4-(1-(4-((5-bromo-4-((8-(dimethylphosphoryl)-3-methylisoquinolin-7-yl)amino)pyrimidin-2-yl)amino)-2-ethyl-5-methoxyphenyl)piperidin-4-yl)piperazin-1-yl)ethyl)-2,6-difluorophenyl)piperidine-2,6-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2.1: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere 3.1: hydrogenchloride / water monomer / 1 h / 20 °C 4.1: glacial acetic acid; Iodine monochloride / 1 h / 20 °C 5.1: tripotassium phosphate tribasic; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 6.1: lithium hexamethyldisilazane / N,N-dimethyl-formamide / 3 h / 0 - 20 °C 7.1: toluene-4-sulfonic acid / butan-1-ol / 13 h / 100 °C 8.1: dichloromethane / 1 h / 20 °C 8.2: 12 h / 20 °C
  • 46
  • [ 1013-88-3 ]
  • [ 1029720-65-7 ]
  • N-(3-chloroisoquinolin-7-yl)-1,1-diphenylmethanimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
69.8% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 14h; Inert atmosphere; 200.8 Step 8: N-(3-chloroisoquinolin-7-yl)-1,1-diphenylmethanimine To a solution of 7-bromo-3-chloroisoquinoline (2.5 g,13.8 mmol) and diphenylmethanimine (3.35 g,13.8 mmol) in dioxane (100 mL) was added Cs 2CO 3 (9 g,27.6 mmol) at 20 . Pd 2 (dba) 3 (1.26 g,1.4 mmol) and BINAP (1.72 g,2.8 mmol) was added to the mixture at 20 . The suspension was degassed under vacuum and purged with N 2 three times. Then the mixture was stirred at 100 for 14 hrs. The mixture was filtered and concentrated in vacuum. The residue was purified by column chromatography (DCM/MeOH =10/1 to 5/1) . N-(3-chloroisoquinolin-7-yl)-1,1-diphenylmethanimine (3.3 g,69.8%) was obtained. [M+H] + =343.1.
69.8% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 100℃; for 14h; Inert atmosphere; 200.8 Step 8: N-(3-chloroisoquinolin-7-yl)-1,1-diphenylmethanimine To a solution of 7-bromo-3-chloroisoquinoline (2.5 g,13.8 mmol) and diphenylmethanimine (3.35 g,13.8 mmol) in dioxane (100 mL) was added Cs 2CO 3 (9 g,27.6 mmol) at 20 . Pd 2 (dba) 3 (1.26 g,1.4 mmol) and BINAP (1.72 g,2.8 mmol) was added to the mixture at 20 . The suspension was degassed under vacuum and purged with N 2 three times. Then the mixture was stirred at 100 for 14 hrs. The mixture was filtered and concentrated in vacuum. The residue was purified by column chromatography (DCM/MeOH =10/1 to 5/1) . N-(3-chloroisoquinolin-7-yl)-1,1-diphenylmethanimine (3.3 g,69.8%) was obtained. [M+H] + =343.1.
  • 47
  • [ 1013-88-3 ]
  • [ 1029720-65-7 ]
  • N-(3-methylisoquinolin-7-yl)-1,1-diphenylmethanimine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cs2CO3; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 14 h / 100 °C / Inert atmosphere 2: potassium carbonate; palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere
  • 48
  • [ 120-72-9 ]
  • [ 1029720-65-7 ]
  • [ 100-39-0 ]
  • 2-benzyl-7-bromo-1-(1H-indol-3-yl)-1,4-dihydroisoquinolin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With water monomer; anhydrous Sodium acetate In tert-Amyl alcohol at 100℃; for 8h; Inert atmosphere; Schlenk technique; Sealed tube;
Same Skeleton Products
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