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[ CAS No. 1029720-67-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 1029720-67-9
Chemical Structure| 1029720-67-9
Chemical Structure| 1029720-67-9
Structure of 1029720-67-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1029720-67-9 ]

CAS No. :1029720-67-9 MDL No. :MFCD11044700
Formula : C9H5BrClN Boiling Point : -
Linear Structure Formula :- InChI Key :WSNRPWWRYCNOJB-UHFFFAOYSA-N
M.W : 242.50 Pubchem ID :51341979
Synonyms :

Calculated chemistry of [ 1029720-67-9 ]      Expand+

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) : 2.33
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 : 1.6

Safety of [ 1029720-67-9 ]

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 [ 1029720-67-9 ]

* 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 [ 1029720-67-9 ]

[ 1029720-67-9 ] Synthesis Path-Downstream   1~35

  • 1
  • [ 1029720-67-9 ]
  • [ 535-13-7 ]
  • [ 1254715-58-6 ]
YieldReaction ConditionsOperation in experiment
18% With manganese In N,N-dimethyl-formamide at 60 - 65℃; 6.6.18.g Step-f product (0.5 g, 0.002 mol) was dissolved in dry dimethylformamide (4 mL). 2- chloroethylpropionate (0.36 g, 0.002 mol), NiBr2.bipy (0.06 g, 0.164 mol) and Mn dust (0.226 g, 0.004 mol) were added simaltaneously. It was degasified and trifloroacetic acid (4 μL) was added to the solution. It was heated to 60 - 65 0C for 7 hours. After starting was consumed water (40 mL) was added and the mixture was passed through celite bed. The filtrate was extracted with ethyl acetate (2 x 50 mL) The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100- 200, eluent: 15% ethyl acetate in hexane) to afford the pure compound (100 mg, 18% yield).
  • 2
  • [ 58142-49-7 ]
  • [ 1029720-67-9 ]
YieldReaction ConditionsOperation in experiment
81% Step-e product (13 g, 0.073 mol) was taken in hydrobromic acid (35 mL) and water (35 mL) and heated to 50 0C for 30 minutes. It was then allowed to cool to 0 to -5 0C. Sodium nitrite (6.8 g,) dissolved in water (35 mL) was added drop wise for 10 minutes maintaining temperature between 0 to -5 0C. It was allowed to stir at 0 0C for 10 minutes. It was added to copper bromide (13.8 g) in hydrobromic acid (115 mL) slowly at 75 0C for 10 minutes and allowed to come at room temperature and stirred for 2 hours. After starting was consumed it was basified with sodium hydroxide solution (10%, 100 mL) and extracted with ethyl acetate (3 x 200 mL). The combined organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the crude compound. The crude compound was purified by column chromatography (silica gel: 100-200; eluent: 10% ethyl acetate in hexane) to afford the pure compound (13 g, 81% yield).
  • 3
  • [ 879487-10-2 ]
  • [ 1029720-67-9 ]
  • [ 1578245-82-5 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; at 110℃; for 1h;Microwave irradiation; General procedure: The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 3- Chloro-5-(1 -isopropyl-1 -/-pyrazol- NMR (500 MHz, CDCI3): delta 9.10 (d, J = 4- yl)isoquinoline 0.8 Hz, 1 H), 8.00 (t, J = 0.9 Hz, 1 H), 7.92 (dt, J = 8.2, 1 .1 Hz, 1 H), 7.76 (d, J = 0.8 Hz, 1 H), 7.72 - 7.66 (m, 2H), 7.61 (dd, J = 8.2, 7.1 Hz, 1 H), 4.64 (hept, J = 6.7 Hz, 1 H), 1 .64 (d, J = 6.7 Hz, 6H). LCMS (ESI) Rt = 2.56 minutes MS m/z 272 [M+H]+ N-N r- Using 1 -isopropyl-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole in Method 9 at 1 10C for 60 minutes.
  • 4
  • [ 1029720-67-9 ]
  • [ 761446-44-0 ]
  • [ 1578245-81-4 ]
YieldReaction ConditionsOperation in experiment
100% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 105℃; for 1.5h; Microwave irradiation;
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 110℃; for 2h; Microwave irradiation; 7 The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 3-Chloro-5-(1 -methyl-1 A7-pyrazol-4- NMR (500 MHz, CDCI3): δ 9.10 (d, J = yl)isoquinoline 0.9 Hz, 1 H), 8.02 - 7.97 (m, 1 H), 7.97 - 7.89 (m, 1 H), 7.74 (d, J = 0.8 Hz, 1 H), 7.72 - 7.59 (m, 3H), 4.07 (s, 3H). LCMS (ESI) Rt = 2.30 minutes MS m/z 244 [M+H]+ Using 1 -methyl-4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 -/-pyrazole in Method 9 -N at 1 1 0 for 120 minutes.
  • 5
  • [ 1029720-67-9 ]
  • [ 1578243-56-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene; N,N-dimethyl-formamide / 2 h / 140 °C / Microwave irradiation
  • 6
  • [ 1029720-67-9 ]
  • [ 1578243-72-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene; N,N-dimethyl-formamide / 2 h / 140 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C 4: acetic acid; sodium tris(acetoxy)borohydride / dichloromethane; methanol; water / 1 h / 20 °C
  • 7
  • [ 1029720-67-9 ]
  • [ 1578243-73-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene; N,N-dimethyl-formamide / 2 h / 140 °C / Microwave irradiation 3: trifluoroacetic acid / dichloromethane / 16 h / 0 - 20 °C
  • 8
  • [ 1029720-67-9 ]
  • [ 1578245-75-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 190 °C / Microwave irradiation
  • 9
  • [ 1029720-67-9 ]
  • [ 1578245-76-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 20 °C 2.2: 1 h / 80 °C
  • 10
  • [ 1029720-67-9 ]
  • [ 1578245-78-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / N,N-dimethyl-formamide / 1 h / 100 °C / Microwave irradiation 2: tetrakis(triphenylphosphine) palladium(0); cesium fluoride / methanol; 1,2-dimethoxyethane / 1 h / 150 °C / Microwave irradiation
  • 11
  • [ 1029720-67-9 ]
  • [ 1578243-75-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 110 °C / Microwave irradiation 2: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene; N,N-dimethyl-formamide / 120 °C / Microwave irradiation
  • 12
  • [ 1029720-67-9 ]
  • [ 1578243-81-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 1 h / 105 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / water; <i>tert</i>-butyl alcohol / 3 h / 80 °C / Microwave irradiation
  • 13
  • [ 1029720-67-9 ]
  • [ 1578243-84-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 110 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / water; <i>tert</i>-butyl alcohol / 3 h / 100 °C / Microwave irradiation
  • 14
  • [ 1029720-67-9 ]
  • [ 1578243-86-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 110 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / water; <i>tert</i>-butyl alcohol / 1.5 h / 100 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 1.5 h / 105 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / <i>tert</i>-butyl alcohol; water / 1.5 h / 80 °C / Microwave irradiation
  • 15
  • [ 1029720-67-9 ]
  • [ 1578243-54-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 2 h / 130 °C / Microwave irradiation 2: potassium carbonate / N,N-dimethyl-formamide / 1.5 h / 190 °C / Microwave irradiation 3: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / toluene; N,N-dimethyl-formamide / 2 h / 160 °C / Microwave irradiation
  • 16
  • [ 552846-17-0 ]
  • [ 1029720-67-9 ]
  • [ 1578245-77-8 ]
YieldReaction ConditionsOperation in experiment
37% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 130℃; for 2h; Microwave irradiation; 3; 9 Preparation 3: 3-Chloro-5-(1 A7-pyrazol-4-yl)isoquinoline Method 9 Preparation 3: 3-Chloro-5-(1 A7-pyrazol-4-yl)isoquinoline Method 9 A suspension of 5-bromo-3-chloroisoquinoline (522 mg, 2.15 mmol), ferf-butyl 4- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 -/-pyrazole-1 -carboxylate (697 mg, 2.37 mmol), Pd(dppf)CI2-DCM (182 mg, 0.22 mmol) and Na2C03 (2M, 2.2 ml_, 4.30 mmol) in DME (10 ml_) was stirred at 130 under microwave irradiation for 120 minutes. The reaction mixture was filtered and concentrated in vacuo. The residue was purified using Biotage silica gel column chromatography eluting with between 20-30% EtOAc in cyclohexane to afford the title compound as a yellow solid (182 mg, 37%). 1 H NMR (500 MHz, MeOD): δ 9.15 (d, J = 0.9 Hz, 1 H), 8.09 (dt, J = 8.4, 1 .1 Hz, 1 H), 8.04 (s, broad, 1 H), 8.01 (t, J = 0.9 Hz, 1 H), 7.87 (s, broad, 1 H), 7.84 (dd, J = 7.1 , 1 .2 Hz, 1 H), 7.72 (dd, J = 8.3, 7.2 Hz, 1 H). LCMS (ESI) Rt = 2.17 minutes MS m/z 230 [M+H]+
  • 17
  • [ 877399-74-1 ]
  • [ 1029720-67-9 ]
  • [ 1578245-79-0 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 130℃; for 2h; Microwave irradiation; 5 General procedure: The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane.
  • 18
  • [ 832114-00-8 ]
  • [ 1029720-67-9 ]
  • [ 1578245-80-3 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 110℃; for 1.5h; Microwave irradiation; 6 The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 4-(3-Chloroisoquinolin-5-yl)-3,5- NMR (500 MHz, CDCI3): δ 9.17 (d, J = dimethylisoxazole 0.8 Hz, 1 H), 8.07 (dt, J = 8.3, 1 .1 Hz, 1 H), 7.70 (dd, J = 8.3, 7.0 Hz, 1 H), 7.59 (dd, J = 7.0, 1 .2 Hz, 1 H), 7.45 (t, J = 0.9 Hz, 1 H), 2.30 (s, 3H), 2.13 (s, 3H). LCMS (ESI) Rt = 2.42 minutes MS m/z 259 [M+H]+ Using 3,5-dimethyl-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)isoxazole in Method N-0 9 at 1 10 for 90 minutes.
  • 19
  • [ 1046832-21-6 ]
  • [ 1029720-67-9 ]
  • [ 1578245-83-6 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In 1,2-dimethoxyethane; at 130℃; for 1h;Microwave irradiation; The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 3- Chloro-5-(1 ,3-dimethyl-1 f/-pyrazol- NMR (500 MHz, CDCI3): delta 9.10 (d, J = 4- yl)isoquinoline 0.8 Hz, 1 H), 7.95 (ddd, J = 7.8, 1 .5, 0.9 Hz, 1 H), 7.70 (t, J = 0.9 Hz, 1 H), 7.66 - 7.57 (m, 2H), 7.43 (s, 1 H), 3.98 (s, 3H), 2.1 7 (s, 3H). LCMS (ESI) Rt = 2.39 minutes MS m/z 258 [M+H]+ Using 1 ,3-dimethyl-4-(4,4,5,5-tetramethyl- N-N 1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole in Method 9 at 130 C for 60 minutes.
  • 20
  • [ 1029720-67-9 ]
  • [ 1692-25-7 ]
  • [ 1578245-88-1 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 110℃; for 1h; Microwave irradiation; 14 The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 14 3-Chloro-5-(pyridin-3-yl)isoquinoline NMR (500 MHz, CDCI3): δ 9.14 (d, J = 0.9 Hz, 1 H), 8.81 - 8.68 (m, 2H), 8.10 - CIA J 7.99 (m, 1 H), 7.80 (ddd, J = 7.7, 2.3, 1 .7 Hz, 1 H), 7.75 - 7.62 (m, 3H), 7.49 (ddd, J = 7.8, 4.8, 0.9 Hz, 1 H). LCMS (ESI) Rt = 2.04 minutes MS m/z 241 [M+H]+ Using pyridin-3-ylboronic acid in Method 9 at 1 1 0 for 60 minutes.
  • 21
  • [ 1029720-67-9 ]
  • [ 1692-25-7 ]
  • [ 1578243-74-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate / 1,2-dimethoxyethane / 1 h / 110 °C / Microwave irradiation 2: palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / toluene; N,N-dimethyl-formamide / 2 h / 120 °C / Microwave irradiation
  • 22
  • [ 13331-23-2 ]
  • [ 1029720-67-9 ]
  • [ 1578245-89-2 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 105℃; for 1h; Microwave irradiation; 15 The following Preparations were prepared according to Methods 9 or 10 (Preparations 3 or 4) above using the appropriate chloroisoquinoline and the appropriate cross-coupling partner as described. The Preparations were purified according to the methods described or as described below: Method A: Biotage silica gel column chromatography eluting with 30-35% EtOAc in cyclohexane. Method B: Biota e silica gel column chromatography eluting with 50% EtOAc in cyclohexane. 15 3-Chloro-5-(furan-2-yl)isoquinoline ' H NMR (500 MHz, CDCI3): δ 9.09 (s, 1 H), 8.33 (s, 1 H), 7.99 - 7.90 (m, 2H), 7.71 - 7.55 (m, 2H), 6.79 (dd, J = 3A, 0.6 Hz, 1 H), 6.62 (dd, J = 3.4, 1 .8 Hz, 1 H). LCMS (ESI) MS m/z 230 [M+H]+ HRMS (ESI) MS m/z calcd for C13H9CINO [M+H]+ 230.0367, found 230.0343. Using furan-2-ylboronic acid in Method 9 at 105°C for 1 hour.
  • 23
  • [ 1029720-67-9 ]
  • [ 73183-34-3 ]
  • [ 1578245-90-5 ]
YieldReaction ConditionsOperation in experiment
41% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation; 16 Preparation 16: 3-Chloro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)isoquinoline Preparation 16: 3-Chloro-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)isoquinoline A mixture of 5-bromo-3-c loroisoquinoline (63 mg, 0.41 mmol), KOAc (63 mg, 0.41 mmol), Pd(dppf)CI2 FontWeight="Bold" FontSize="10" DCM (22 mg, 0.03 mmol) and bis(pinacolato)diboron (63 mg, 0.41 mmol) in DMF (8 mL) was stirred at 100°C under microwave irradiation for 60 minutes. The reaction mixture was filtered, diluted with NaCI solution and extracted with EtOAc. The crude was purified by Biotage silica gel column chromatography eluting with 20% EtOAc/cyclohexane to afford the title compound as yellow oil (170 mg, 41 %). 1H NMR (500 MHz, CDCI3): δ 9.06 (d, J = 0.9 Hz, 1 H), 8.66 - 8.64 (m, 1 H), 8.31 (dd, J = 6.9, 1 .4 Hz, 1 H), 8.15 - 7.96 (m, 1 H), 7.60 (dd, J = 8.2, 6.9 Hz, 1 H), 1 .44 (s, 12H). LCMS (ESI) Rt = 3.02 minutes MS m/z 290 [M+H]+
  • 24
  • [ 1029720-67-9 ]
  • C20H16N2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 1 h / 105 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / <i>tert</i>-butyl alcohol; water / 3 h / 80 °C / Microwave irradiation
  • 25
  • [ 1029720-67-9 ]
  • [ 1578243-82-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,2-dimethoxyethane / 1.5 h / 105 °C / Microwave irradiation 2: tert-butyl XPhos; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate / <i>tert</i>-butyl alcohol; water / 1.5 h / 80 °C / Microwave irradiation
  • 27
  • [ 1029720-67-9 ]
  • (E)-3-(3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acrylonitrile [ No CAS ]
  • (E)-3-(4-(3-chloroisoquinolin-5-yl)-3,5-dimethylphenyl)acrylonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water; N,N-dimethyl-formamide at 80℃; for 0.5h; Inert atmosphere; 5.1 Step 1: Synthesis of (E)-3-(4-(3-chloroisoquinolin-5-yl)-3,5-dimethylphenyl)acrylonitrile (compound 5a) 5-Bromo-3-chloroisoquinoline (500 mg, 2.06 mmol; SynQuest Laboratories; 3H32-D-Z7), compound le (759 mg, 2.68 mniol), potassium phosphate tribasic (656 mg, 3.09 mmol) and l,1’-bis(di-terl-butylphosphino)ferrocene palladium dichloride (134 mg, 0.21 mmol) were dissolved in dimethylformamide:water mixture (85:15, 40 mL) under argon. The reaction was heated to 80°C for 30 minutes. The reaction mixture was cooled down to room temperature and diluted with water and ethyl acetate. The organic layer was separated and washed twice with brine, dried over magnesium sulfate, 0.5 volume equivalent of hexane added and this mixture was filtered through a 2 cm layer of silica gel which was washed withadditional ethyl acetate. Combined organics were concentrated down under reduced pressure and the residue was treated with hexane in a sonic bath. The solid product was filtered off and washed twice with hexane to afford the title compound 5a. ‘H NMR (400 MHz, DMSO-do) 8 9.34 (s, 1H), 8.31 -8.17 (m, 1H), 7.84 (dd,J= 8.2, 7.1 Hz, IH), 7.74-7.60 (m, 2H), 7.56 (s, 2H), 7.00 (s, I H), 6.53 (d, J = 16.7 Hz, I H), 1.84 (s, 6H). LCMS (mlz) 319.2 [M+HJ, Tr =2.83 mm (LCMS method 1).
  • 28
  • [ 7742-73-6 ]
  • [ 1029720-67-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid; N-Bromosuccinimide / acetonitrile / 90 h / 20 °C 2: acetic acid; tin; hydrogenchloride / 0.5 h / 60 °C
  • 29
  • [ 1029720-67-9 ]
  • [ 33513-42-7 ]
  • 3-chloroisoquinoline-5-carbaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
30.7% Stage #1: 5-bromo-3-chloroisoquinoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; 1.276.3 Step 3 Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-bromo-3-chloroisoquinoline (3.00 g, 12.371 mmol, 1.00 equiv), THF (30.00 mL). This was followed by the addition of n-BuLi in hexanes (5.9 mL, 14.862 mmol, 1.20 equiv) dropwise with stirring at -78 °C. The resulting solution was stirred for 0.5 hr at -78 °C. To this was added DMF (2.71 g, 37.113 mmol, 3.00 equiv) dropwise with stirring at -78 °C. The resulting solution was warmed up to room temperature and stirred for an additional 2 hr. The reaction was then quenched by the addition of 100 mL of NH4Cl. The resulting solution was extracted with 2x50 mL of ethyl acetate. Organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered, and the filtrate was concentrated. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 730 mg (30.7%) of 3-chloroisoquinoline-5-carbaldehyde as a light yellow solid. LCMS (ES) [M+1]+ m/z 192.
30.7% Stage #1: 5-bromo-3-chloroisoquinoline With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; 1.276.3 Step 3 Into a 100-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 5-bromo-3-chloroisoquinoline (3.00 g, 12.371 mmol, 1.00 equiv), THF (30.00 mL). This was followed by the addition of n-BuLi in hexanes (5.9 mL, 14.862 mmol, 1.20 equiv) dropwise with stirring at -78 °C. The resulting solution was stirred for 0.5 hr at -78 °C. To this was added DMF (2.71 g, 37.113 mmol, 3.00 equiv) dropwise with stirring at -78 °C. The resulting solution was warmed up to room temperature and stirred for an additional 2 hr. The reaction was then quenched by the addition of 100 mL of NH4Cl. The resulting solution was extracted with 2x50 mL of ethyl acetate. Organic layers were combined, washed with brine and dried over anhydrous sodium sulfate. The mixture was filtered, and the filtrate was concentrated. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1). This resulted in 730 mg (30.7%) of 3-chloroisoquinoline-5-carbaldehyde as a light yellow solid. LCMS (ES) [M+1]+ m/z 192.
  • 30
  • [ 1215767-89-7 ]
  • [ 1029720-67-9 ]
YieldReaction ConditionsOperation in experiment
41.87% With hydrogenchloride; tin; acetic acid at 60℃; for 0.5h; 1.276.2 Step 2 Into a 500-mL round-bottom flask was placed 5-bromo-1,3- dichloroisoquinoline (15.00 g, 54.163 mmol, 1.00 equiv), AcOH (150.00 mL), HCl (30.00 mL) and Sn (19.34 g, 162.490 mmol, 3 equiv). The resulting solution was stirred for 0.5 hr at 60 °C. The resulting solution was extracted with 3x200 mL of ethyl acetate, organic layers were combined, washed with 3 x200 ml of brine and filtered. The filtrate was concentrated and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 5.5 g (41.87%) of 5-bromo-3- chloroisoquinoline as a light yellow solid. LCMS (ES) [M+1]+ m/z 242
41.87% With hydrogenchloride; tin; acetic acid at 60℃; for 0.5h; 1.276.2 Step 2 Into a 500-mL round-bottom flask was placed 5-bromo-1,3- dichloroisoquinoline (15.00 g, 54.163 mmol, 1.00 equiv), AcOH (150.00 mL), HCl (30.00 mL) and Sn (19.34 g, 162.490 mmol, 3 equiv). The resulting solution was stirred for 0.5 hr at 60 °C. The resulting solution was extracted with 3x200 mL of ethyl acetate, organic layers were combined, washed with 3 x200 ml of brine and filtered. The filtrate was concentrated and the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5). This resulted in 5.5 g (41.87%) of 5-bromo-3- chloroisoquinoline as a light yellow solid. LCMS (ES) [M+1]+ m/z 242
  • 31
  • [ 1029720-67-9 ]
  • (3-chloroisoquinolin-5-yl)methanol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C
  • 32
  • [ 1029720-67-9 ]
  • 5-[[(tert-butyldimethylsilyl)oxy]methyl]-3-chloroisoquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 12 h / 20 °C
  • 33
  • [ 1029720-67-9 ]
  • 2-((2-(5 -(((tert-butyldimethylsilyl)oxy)methyl)i soquinolin-3 -yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)(methyl)amino)-N-(6-methylpyridin-3-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 12 h / 20 °C 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 100 °C 4.2: 100 °C
  • 34
  • [ 1029720-67-9 ]
  • 2-( { 2-[5-(hydroxymethyl)isoquinolin-3 -yl] -5H, 6H,7H-cyclopenta[d]pyrimidin-4-yl } (methyl)amino)-N-(6-methylpyridin-3 -yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 1.2: 2 h / -78 - 20 °C 2.1: sodium tetrahydroborate / tetrahydrofuran / 2 h / 20 °C 3.1: 1H-imidazole / dichloromethane / 12 h / 20 °C 4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 100 °C 4.2: 100 °C 5.1: triethylamine / tetrahydrofuran / 12 h / 20 °C
  • 35
  • [ 1029720-67-9 ]
  • [ 1337882-22-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / propan-1-ol / 5 min / Inert atmosphere 1.2: 3 h / 90 °C / Inert atmosphere 2.1: osmium(VIII) oxide / 1,4-dioxane; <i>tert</i>-butyl alcohol / 15 min 2.2: 16 h / 20 °C
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