Select Region or Location
Americas
  • Argentina
  • Brazil
  • Canada
  • Mexico
  • United States
  • Other Americas
Europe
  • Austria
  • Belgium
  • Bulgaria
  • Croatia/Hrvatska
  • Cyprus
  • Czech Republic
  • Denmark
  • Estonia
  • Finland
  • France
  • Germany
  • Greece
  • Hungary
  • Ireland
  • Italy
  • Latvia
  • Liechtenstein
  • Lithuania
  • Luxembourg
  • Malta
  • Netherlands
  • Norway
  • Poland
  • Portugal
  • Romania
  • Slovak Republic
  • Slovenia
  • Spain
  • Sweden
  • Switzerland
  • Turkey
  • United Kingdom
  • Other Europe
Asia Pacific
  • Australia
  • China
  • India
  • Indonesia
  • Japan
  • Korea, Republic of
  • Malaysia
  • New Zealand
  • Philippines
  • Singapore
  • Thailand
  • Vietnam
  • Other Asia Pacific
Africa And Middle East
  • Egypt
  • Israel
  • Other Africa And Middle East
USD
Home Cart Sign in  
Chemical Structure| 215453-53-5 Chemical Structure| 215453-53-5

Structure of 215453-53-5

Chemical Structure| 215453-53-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

DE Stock

US Stock

Asia Stock

Global Stock

In Stock
{[ item.pr_size ]}{[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

  • {[ item.pr_size ]}
    {[ size_append_text(item.pr_size, proInfo.prAm, 'list') ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 215453-53-5 ]

CAS No. :215453-53-5
Formula : C9H7BrN2
M.W : 223.07
SMILES Code : BrC1=CC=C2C(=C1)C(=NC=C2)N
English Name :7-Bromoisoquinolin-1-amine
MDL No. :MFCD07374397
InChI Key :PLOCDXILPIGHEZ-UHFFFAOYSA-N
Pubchem ID :22665734

Safety of [ 215453-53-5 ]

Computational Chemistry of [ 215453-53-5 ] Show Less

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 1.0
Molar Refractivity 53.85
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

38.91 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.79
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.59
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.59
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.31
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.4
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.34

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.47
Solubility 0.0753 mg/ml ; 0.000338 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.06
Solubility 0.196 mg/ml ; 0.000879 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-4.2
Solubility 0.014 mg/ml ; 0.000063 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.82 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.53

Application In Synthesis of [ 215453-53-5 ]

* 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 [ 215453-53-5 ]

[ 215453-53-5 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 215453-51-3 ]
  • [ 215453-53-5 ]
YieldReaction ConditionsOperation in experiment
88.7% With 1-methyl-pyrrolidin-2-one; ammonium hydroxide In water at 148℃; for 20h; Sealed tube;
72.42% With ammonium hydroxide In 1-methyl-pyrrolidin-2-one for 15h; 1 Example 1. Preparation of N-(l-aminoisoquinolin-7-yl)-N-methylcyanamide (1) To a solution of compound 1.5 (3 g, 12.4 mmol, 1 eq) in NMP (30 mL) was addedNH.HzO (30 mL). The mixture was stirred 150°C for 15 hours. The reaction mixture wasquenched by addition H20 100 mL at 25 °C, and then extracted with EtOAC (100 mL x 3). The combined organic layers were washed with saturated brines (15 mL x 1), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The residue was purified by column chromatography (Si02, Petroleum ether/Ethylacetate=1:1). Compound 1.4 (2.0 g, 9 mmol, 72.42% yield) was obtained as a brown oil. LCMS (ESI): m/z: [M + H] calcd for C9H7N2Br:223; found 223; RT=1.049 mm.
Multi-step reaction with 2 steps 1: KOH; PhOH / 2 h / 140 °C 2: NH4OAc / 14 h / 150 °C
  • 3
  • [ 215453-53-5 ]
  • [ 252970-88-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: pyridine / 1 h / 125 °C 2: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3: NaBH4 / tetrahydrofuran; methanol / 0.08 h / 20 °C 4: Et3N / CH2Cl2 / 2 h / 20 °C 5: LiCl / tetrahydrofuran / 16 h / 20 °C 6: EtONa / ethanol; dioxane / 2 h / 80 °C 7: aq. HCl / acetic acid / 16 h / 100 °C 8: 100 percent / SOCl2 / 2 h / 50 °C
  • 4
  • [ 215453-53-5 ]
  • [ 1392209-81-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / 1 h / 125 °C 2: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C
  • 5
  • [ 215453-53-5 ]
  • [ 252971-66-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 11 steps 1: pyridine / 1 h / 125 °C 2: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3: NaBH4 / tetrahydrofuran; methanol / 0.08 h / 20 °C 4: Et3N / CH2Cl2 / 2 h / 20 °C 5: LiCl / tetrahydrofuran / 16 h / 20 °C 6: EtONa / ethanol; dioxane / 2 h / 80 °C 7: aq. HCl / acetic acid / 16 h / 100 °C 8: 100 percent / SOCl2 / 2 h / 50 °C 9: Et3N / CH2Cl2 / 1 h / 0 - 20 °C 10: aq. NaOH / dioxane / 20 °C 11: TBTU / dimethylformamide / 16 h / 20 °C
Multi-step reaction with 11 steps 1: pyridine / 1 h / 125 °C 2: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C 3: NaBH4 / tetrahydrofuran; methanol / 0.08 h / 20 °C 4: Et3N / CH2Cl2 / 2 h / 20 °C 5: LiCl / tetrahydrofuran / 16 h / 20 °C 6: EtONa / ethanol; dioxane / 2 h / 80 °C 7: aq. HCl / acetic acid / 16 h / 100 °C 8: 100 percent / Et3N / methanol / 20 °C 9: TBTU / dimethylformamide / 1 h / 20 °C 10: TFA / CH2Cl2 / 1 h / 20 °C 11: Et3N / CH2Cl2 / 1 h / 0 - 20 °C
  • 6
  • [ 24424-99-5 ]
  • [ 215453-53-5 ]
  • [ 288309-20-6 ]
YieldReaction ConditionsOperation in experiment
69.32% With dmap; triethylamine In tetrahydrofuran at 25℃; for 15h; 1 To a solution of compound 1.4 (1.90 g, 8.52 mmol, 1 eq) in THF (40 mL) wasadded TEA (3.45 g, 34.08 mmol, 4.73 mL, 4 eq) and Boc20 (4.65 g, 21.30 mmol, 4.89 mL,2.50 eq) and DMAP (312.18 mg, 2.56 mmol, 0.30 eq). The mixture was stirred at 25 °C for15 hours. The reaction mixture was quenched by addition H20 50 mL at 25°C and extracted with EtOAc (5OmL x 3). The combined organic layers were washed with saturated brines (20 mL x 1), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a crude product. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate=2: 1). Compound 1.3 (2.50 g, 5.91 mmol, 69.32% yield) wasobtained as a yellow oil. ‘HNMR (400 MHz, methanol-d4) ö ppm 1.16 - 1.49 (m, 21 H) 7.89 (d, J5.77 Hz, 1 H) 7.92 - 8.03 (m, 2 H) 8.10 (s, 1 H) 8.42 (d, J=5.77 Hz, 1 H). LCMS (ESI):m/z: [M + H] calcd for C19H23N2BrO4:423; found 423; RT=0.957 mm.
68% With dmap In dichloromethane at 20℃; for 16h; A Step A: bis-tert-Butyl (7-bromoisoquinolin-1-yl)carbamate. In a 1 L round- bottomed flask, DMAP (0.13 g, 1.05 mmol) was added to a suspension of 7- bromoisoquinolin-1-amine (4.7 g, 21 mmol) and di-tert-butyl decarbonate (9.2 g, 42 mmol) in DCM (210 mL). The resulting mixture was stirred at rt for 16 h, the resulting solid was collected filtration, and triturated with ethyl acetate to afford bis-tert-butyl (7- bromoisoquinolin-1-yl)carbamate (6.1 g, 68%) as a colorless solid. MS (ESI): mass calcd. for C19H23BrN2O4, 422.08; m/z found, 421.3, 423.1 [M+H]+.1H NMR (400 MHz, Chloroform-d) d 8.47 (d, J = 5.7 Hz, 1H), 8.15 (s, 1H), 7.84 - 7.73 (m, 2H), 7.65 (dd, J = 5.7, 1.0 Hz, 1H), 1.36 (s, 18H).
64% With dmap In ethyl acetate; acetonitrile 17.F Part F. Part F. 1-[Bis(t-butoxycarbonyl)amino]-7-bromoisoquinoline A solution of 740 mg (3.32 mmol) of 1-amino-7-bromoisoquinoline in 50 mL of acetonitrile was treated with 1.4 mL of N,N-diiospropylethylamine and 100 mg of 4-(N,N-dimethylamino)pyridine, followed by 3.0 g (4.1 eq) of di-t-butyldicarbonate, and the reaction was stirred at 40° C. for 1 hr. By HPLC analysis, there was still some starting amino compound that remained, so another 1.0 g of di-t-butyldicarbonate were added, and the reaction was stirred at 40° C. for another 30 min. The reaction mixture was concentrated to give a dark oil, which was subjected to flash column chromatography on silica gel with 20% EtOAc in hexanes to give 736 mg of the desired product as a light yellow solid. Also isolated were 156 mg of product as a somewhat less pure light yellow solid, making the total yield 64%.
64% With dmap In ethyl acetate; acetonitrile 40.6 Part 6. Part 6. 1-[Bis(t-butoxycarbonyl)amino]-7-bromoisoquinoline A solution of 740 mg (3.32 mmol) of 1-amino-7-bromoisoquinoline in 50 mL of acetonitrile was treated with 1.4 mL of N,N-diiospropylethylamine and 100 mg of 4-(N,N-dimethylamino)pyridine, followed by 3.0 g (4.1 eq) of di-t-butyldicarbonate, and the reaction was stirred at 40° C. for 1 hr. By HPLC analysis, there was still some starting amino compound that remained, so another 1.0 g of di-t-butyldicarbonate were added, and the reaction was stirred at 40° C. for another 30 min. The reaction mixture was concentrated to give a dark oil, which was subjected to flash column chromatography on silica gel with 20% ethyl acetate in hexanes to give 736 mg of the desired product as a light yellow solid. Also isolated were 156 mg of product as a somewhat less pure fight yellow solid, making the total yield 64%.

  • 7
  • [ 26377-17-3 ]
  • [ 144-62-7 ]
  • [ 215453-53-5 ]
  • [ 1202396-70-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: ethyl 3-oxo-3-(4-pyridyl)propanoate; 7-bromoisoquinolin-1-amine With ammonium acetate at 140℃; for 12h; Stage #2: In diphenyl ether-biphenyl eutectic at 210℃; for 8h; Stage #3: oxalic acid 1 Example 1 (Compound No. 2 of table 1) 10-Bromo-2-pyridin-4-yl-4H-pyrimido[2,1-a]isoquinolin-4-one oxalate (1:1) ; To a mixture of 0.1g (0.38 mmol) of 7-bromoisoquinolin-1-amine (synthesis described in WO9847876) and 0.134g (0.69 mmol) of ethyl 3-(4-pyridinyl)-3-oxopropionate were added 0.059g (0.77 mmol) of ammonium acetate. The reaction mixture was heated at 140°C for 12 hours. Then 2ml of Dowtherm A were added and the resulting mixture was allowed to stir at 210°C for 8 hours. After cooling, water was added and the resulting solution was acidified using isopropanol hydrochloride 6N. Dowtherm A was extracted using diethyl ether and the aqueous phase was basified by an aqueous solution of sodium hydroxide (30%) and extracted with dichloromethane. The extracts were dried over sodium sulphate and evaporated. The residue obtained was purified by chromatography on silica gel eluting with a mixture of dichloromethane/methanol in the proportions 99/1 to 95/5 to give 0.041g (30%) of the desired compound which was transformed into the oxalate salt in the usual manner to give the pure product as a solid. MP: 244-246°C RMN 1H (DMSO-d6; 200 MHz) δ (ppm) : 9.25 (s, 1H), 8.80 (d, 2H), 8.70 (d, 1H), 8.30 (d, 2H), 8.10 (dd, 1H), 8.00 (dd, 1H), 7.65 (d, 1H), 7.40 (s, 1H).
  • 8
  • [ 73183-34-3 ]
  • [ 215453-53-5 ]
  • [ 1210048-27-3 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate In 1,4-dioxane at 130℃; Inert atmosphere; 113A.1 Under an argon atmosphere, 500 mg (2.241 mmol) of 7-bromo-isoquinolin-l -amine [Rewinkel et al., Bioorg. Med. Chem. Lett. 1999, 9, 2837] was dissolved in 4 ml dioxane. Then 660 mg (6.72 mmol) potassium acetate, 146 mg (0.179 mmol) of l,r-bis-(diphenylphosphino)ferrocene- palladium(II) chloride-dichloromethane complex and 626 mg (2.465 mmol) of 4,4,4'4'5,5,5'5'- octamethyl-2,2'-bi-l,3,2-dioxaborolan were added. The reaction mixture was stirred overnight at an oil bath temperature of 1300C. After cooling, dichloromethane was added and it was filtered on kieselguhr. Then it was washed again with ethyl acetate. The filtrate was concentrated in a rotary evaporator at reduced pressure and dried under high vacuum. We obtained 776 mg of 7-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)isoquinolin-l-amine [63%, (LC-MS)] as raw product. This was reacted subsequently without further purification.
  • 9
  • [ 215453-53-5 ]
  • [ 1449278-41-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr 4: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 5: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C 6: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C / Inert atmosphere 7: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere
  • 10
  • [ 215453-53-5 ]
  • [ 1449276-76-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr 4: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 5: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C 6: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C / Inert atmosphere 7: sodium tetrahydroborate / methanol / 1 h / 20 °C / Inert atmosphere 8: hydrogenchloride / water; tetrahydrofuran / 5 h / 20 °C
  • 11
  • [ 215453-53-5 ]
  • [ 1449278-32-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere
  • 12
  • [ 215453-53-5 ]
  • [ 1449278-40-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr 4: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere 5: sodium hydroxide / water; methanol; tetrahydrofuran / 20 °C 6: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 20 °C / Inert atmosphere
  • 13
  • [ 215453-53-5 ]
  • [ 1449278-33-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr
  • 14
  • [ 215453-53-5 ]
  • [ 1803004-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; 1,4-dioxane / 15 h / Inert atmosphere; Reflux 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere 3: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; dmap / 70 °C / 2585.81 Torr 4: dmap; triethylamine / dichloromethane / 48 h / 20 °C / Inert atmosphere
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 215453-53-5 ]

Bromides

Chemical Structure| 215453-26-2

A323648 [215453-26-2]

6-Bromoisoquinolin-1-ylamine

Similarity: 1.00

Chemical Structure| 852570-80-0

A113105 [852570-80-0]

5-Bromoisoquinolin-1-amine

Similarity: 0.87

Chemical Structure| 58794-09-5

A142957 [58794-09-5]

7-Bromoisoquinoline

Similarity: 0.80

Chemical Structure| 55270-27-4

A152719 [55270-27-4]

4-Bromoisoquinolin-1-amine

Similarity: 0.79

Chemical Structure| 63927-22-0

A120543 [63927-22-0]

8-Bromoisoquinoline

Similarity: 0.76

Amines

Chemical Structure| 215453-26-2

A323648 [215453-26-2]

6-Bromoisoquinolin-1-ylamine

Similarity: 1.00

Chemical Structure| 852570-80-0

A113105 [852570-80-0]

5-Bromoisoquinolin-1-amine

Similarity: 0.87

Chemical Structure| 55270-27-4

A152719 [55270-27-4]

4-Bromoisoquinolin-1-amine

Similarity: 0.79

Chemical Structure| 87109-10-2

A106563 [87109-10-2]

3-Phenylpyridin-2-amine

Similarity: 0.79

Chemical Structure| 90721-34-9

A771070 [90721-34-9]

8-Bromoisoquinolin-5-amine

Similarity: 0.76

Related Parent Nucleus of
[ 215453-53-5 ]

Isoquinolines

Chemical Structure| 215453-26-2

A323648 [215453-26-2]

6-Bromoisoquinolin-1-ylamine

Similarity: 1.00

Chemical Structure| 852570-80-0

A113105 [852570-80-0]

5-Bromoisoquinolin-1-amine

Similarity: 0.87

Chemical Structure| 58794-09-5

A142957 [58794-09-5]

7-Bromoisoquinoline

Similarity: 0.80

Chemical Structure| 55270-27-4

A152719 [55270-27-4]

4-Bromoisoquinolin-1-amine

Similarity: 0.79

Chemical Structure| 63927-22-0

A120543 [63927-22-0]

8-Bromoisoquinoline

Similarity: 0.76