33930-63-1|4-Bromo-2-methylisoquinolin-1(2H)-one| Ambeed

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Quality Control of [ 33930-63-1 ] Purity: 97% SDS Specification

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NMR

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Product Details of [ 33930-63-1 ]

CAS No. :	33930-63-1
Formula :	C₁₀H₈BrNO
M.W :	238.08
SMILES Code :	C1=CC=CC2=C1C(=CN(C)C2=O)Br
MDL No. :	MFCD00489133
InChI Key :	YCYRWLPOFCNZPY-UHFFFAOYSA-N
Pubchem ID :	311858

Safety of [ 33930-63-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 33930-63-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	57.17
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	22.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.29
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.3
Log P_o/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.	2.65
Log P_o/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	2.66
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.37

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.1
Solubility	0.189 mg/ml ; 0.000792 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.	-2.02
Solubility	2.29 mg/ml ; 0.00964 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	-4.03
Solubility	0.0223 mg/ml ; 0.0000938 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.	-6.38 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)	1.71

Application In Synthesis of [ 33930-63-1 ]

* 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 [ 33930-63-1 ]

[ 33930-63-1 ] Synthesis Path-Downstream 1~35

2
[ 4594-71-2 ]
[ 33930-63-1 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7076 - 7080.

3
[ 33930-63-1 ]
[ 1005403-35-9 ]
[ 1349798-31-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7076 - 7080.

4
[ 33930-63-1 ]
[ 847818-55-7 ]
2-methyl-4-(1-methylpyrazol-4-yl)isoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 120℃; for 1.0h;Inert atmosphere; Microwave irradiation;	For 3 min, N2 was bubbled through a mixture of <strong>[33930-63-1]4-bromo-2-methylisoquinolin-1(2H)-one</strong> (54 mg, 0.23 mmol), (1-methylpyrazol-4-yl)boronic acid (31 mg, 0.25 mmol), aqueous 2M Na2CO3 (0.375 mL) and Pd(dppf)Cl2 (8 mg, 0.01 mmol) in 1,4-dioxane (1.5 mL) which was then microwaved at 120° C. for 1 h. Work up in a manner similar to Example 18, step 3, and two successive silica gel chromatographies, eluting with 15-80percent EA in hexane over 6 min and continuing 80percent isocratic EA followed by a second chromatography 15-100percent EA in hexane over 6 min and continuing 100percent isocratic EA gave the title compound (28 mg, 0.12 mmol) as a cream solid in 51percent yield. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.54 (s, 3H) 3.92 (s, 3H) 7.50 (s, 1H) 7.55 (ddd, J=8.02, 5.87, 2.27 Hz, 1H) 7.60-7.64 (m, 1H) 7.70-7.80 (m, 2H) 7.95 (s, 1H) 8.31 (d, J=7.83 Hz, 1H). LCMS (M+H)+ 240.

References: [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0480; 0481.

5
[ 33930-63-1 ]
N-[6-(cyclopropylmethoxy)-5(2-methyl-1-oxoisoquinolin-4-yl)pyridin-3-yl]ethanesulfonamide [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

6
[ 33930-63-1 ]
4-[2-(cyclopropylmethoxy)-5-methylsulfonylpyridin-3-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

7
[ 33930-63-1 ]
4-[3-[(4-methoxyphenyl)methoxy]-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

8
[ 33930-63-1 ]
4-[5-(ethylsulfonylmethyl)-2-(2,2,2-trifluoroethoxy)phenyl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

9
[ 33930-63-1 ]
N-[2-ethyl-8-(2-methyl-1-oxoisoquinolin-4-yl)-3,4-dihydro-2H-chromen-6-yl]methanesulfonamide [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

10
[ 33930-63-1 ]
4-(2-cyclopropyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran-7-yl)-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

11
[ 33930-63-1 ]
4-(2-ethyl-5-methylsulfonyl-1-benzofuran-7-yl)-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

12
[ 33930-63-1 ]
4-(2-ethyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran-7-yl)-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

13
[ 33930-63-1 ]
4-[3-(methoxymethyl)-7-methylsulfonyl-2,3-dihydro-1,4-benzodioxin-5-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

14
[ 33930-63-1 ]
4-[2-(cyclopropylmethoxy)-5-(methanesulfonyl)phenyl]-2-methylisoquinolin-1(2H)-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

15
[ 33930-63-1 ]
2-methyl-4-[5-methylsulfonyl-2-(oxolan-3-ylamino)phenyl]isoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

16
[ 33930-63-1 ]
4-[3-(cyclopropylmethoxy)-6-methylsulfonylpyridin-2-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

17
[ 33930-63-1 ]
4-(2-ethoxy-5-ethylsulfonylthiophen-3-yl)-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

18
[ 33930-63-1 ]
4-[3-(cyclopropylmethoxy)-6-ethylsulfonylpyridin-2-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

19
[ 33930-63-1 ]
[ 10365-98-7 ]
4-(3-methoxyphenyl)-2-methylisoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; triphenylphosphine; In 1,4-dioxane; water; at 90℃;	A mixture of <strong>[33930-63-1]4-bromo-2-methylisoquinolin-1(2H)-one</strong> (100 mg, 0.42 mmol), and (3-methoxyphenyl)boronic acid (70 mg, 0.46 mmol), PPh3 (66 mg, 0.25 mmol), Na2CO3 (133 mg, 1.26 mmol), and Pd(dppf)Cl2 (62 mg, 0.084 mmol) in dioxane (2.5 mL) and water (0.5 mL) was heated overnight at 90° C. Extractive work up with ethyl acetate followed by preparative TLC (PE:EA=1:1) gave the title compound (18 mg, 0.07 mmol) as a white solid in 17percent yield. 1H NMR (DMSO, 400 MHz): delta 8.30 (d, 1H, J=7.68), 7.68 (t, 1H, J=7.56), 7.50-7.55 (m, 3H), 7.40 (t, 1H, J=7.44), 6.97-7.00 (m, 3H), 3.78 (s, 3H), 3.54 (s, 3H). MS (m/z, relative intensity): 266 (M+, 1).

References: [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0420; 421.

20
[ 33930-63-1 ]
[ 1310383-78-8 ]
N-benzyl-2-methoxy-5-(2-methyl-1-oxoisoquinolin-4-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 120℃; for 1.0h;Inert atmosphere; Microwave irradiation;	For about 3 min, N2 was bubbled through the mixture of <strong>[33930-63-1]4-bromo-2-methylisoquinolin-1(2H)-one</strong> (56 mg, 0.24 mmol), [3-(benzylsulfamoyl)-4-methoxyphenyl]boronic acid (83 mg, 0.26 mmol), aqueous 2M Na2CO3 (0.375 mL) and Pd(dppf)Cl2 (9 mg, 0.001 mmol) in dioxane (1.5 mL) which was then microwaved at 120° C. for 1 h and then filtered through a plug of anhydrous Na2SO4 using ethyl acetate to transfer and rinse. Silica gel chromatography, eluting with 0-60percent EA in hexane over 6 min and continuing 60percent isocratic EA gave the title compound (60 mg, 0.14 mmol) as a white solid in 58percent yield. 1H NMR (400 MHz, DMSO-d6) delta 3.57 (s, 3H), 3.89 (s, 3H), 4.11 (d, J=6.32 Hz, 2H), 7.16-7.23 (m, 6H), 7.34 (d, J=8.08 Hz, 1H), 7.47 (s, 1H), 7.53-7.59 (m, 2H), 7.65 (d, J=2.27 Hz, 1H), 7.72-7.77 (m, 1H), 7.94 (t, J=6.32 Hz, 1H), 8.34 (d, J=7.33 Hz, 1H). LCMS (M+H)+ 435.

References: [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0423; 0424.

21
[ 33930-63-1 ]
N-benzyl-2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
N-benzyl-2-methoxy-5-(2-methyl-1-oxoisoquinolin-4-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In 1,4-dioxane; water; at 100℃; for 1.0h;Inert atmosphere; Microwave irradiation;	For about 3 min, N2 was bubbled through a mixture of N-benzyl-2-methoxy-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (51 mg, 0.14 mmol), <strong>[33930-63-1]4-bromo-2-methylisoquinolin-1(2H)-one</strong> (30 mg, 0.13 mmol), aqueous 1M K3PO4 (0.3 mL) and Pd(dppf)Cl2 (10 mg, 0.013 mmol) in dioxane (1.15 mL) which was then microwaved at 100° C. for 1 h. Work up similar to Example 15 and purification by silica gel chromatography, eluting with 5-50percent EA in hexane over 4 min and continuing 50percent isocratic EA gave the title compound (37 mg, 0.14 mmol) as a tan solid in 71percent yield. 1H NMR (400 MHz, DMSO-d6) delta 3.57 (s, 3H), 3.97 (s, 3H), 4.52 (d, J=6.06 Hz, 2H), 7.21-7.37 (m, 6H), 7.47-7.51 (m, 2H), 7.56 (td, J=5.37, 2.15 Hz, 2H), 7.68-7.73 (m, 1H), 7.79 (d, J=2.27 Hz, 1H), 8.33 (d, J=7.83 Hz, 1H), 8.79 (t, J=6.06 Hz, 1H). LCMS (M+H)+ 399.

References: [1]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0430; 0431.

22
[ 33930-63-1 ]
4-[5-(cyclopropylmethoxy)-2-(methylsulfonylmethyl)pyrimidin-4-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

23
[ 33930-63-1 ]
4-[5-(cyclopropylmethoxy)-2-methylsulfonylpyrimidin-4-yl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

24
[ 33930-63-1 ]
N-[5-(cyclopropylmethoxy)-4-(2-methyl-1-oxoisoquinolin-4-yl)pyrimidin-2-yl]methanesulfonamide [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

25
[ 33930-63-1 ]
N-[5-(cyclopropylmethoxy)-4-(2-methyl-1-oxoisoquinolin-4-yl)pyrimidin-2-yl]-N-ethylmethanesulfonamide [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

26
[ 33930-63-1 ]
4-(2-fluoro-5-methylsulfonylphenyl)-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

27
[ 33930-63-1 ]
2-methyl-4-[5-methylsulfonyl-2-(oxolan-3-yloxy)phenyl]isoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

28
[ 33930-63-1 ]
4-[2-(trans-4-aminocyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one hydrochloride [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

29
[ 33930-63-1 ]
4-[2-(cis-4-aminocyclohexyl)oxy-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one hydrochloride [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

30
[ 33930-63-1 ]
4-[2-[(trans-4-hydroxycyclohexyl)amino]-5-methylsulfonylphenyl]-2-methylisoquinolin-1-one [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

31
[ 33930-63-1 ]
[4-(cyclopropylmethoxy)-3-(2-methyl-1-oxoisoquinolin-4-yl)phenyl]sulfamate [ No CAS ]

References: [1]Patent: US2015/111885,2015,A1 .

32
[ 33930-63-1 ]
[ 73183-34-3 ]
2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-isoquinolin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos; In 1,4-dioxane; at 60℃; for 12.0h;	[0137] A mixture of 4-bromo-2-methylisoquinolin-l-one (8.0 g, 33.6 mmol), bis(pinacolato)diboron (17.1 g, 67.2 mmol), KOAc (6.6 g, 67.2 mmol), Pd2(dba)3 (3.1 g, 3.36 mmol) and X-Phos (1.6 g, 3.36 mmol) in anhydrous dioxane (200 mL) was stirred at 60°C for 12 hr. The reaction mixture was concentrated, and the residue was purified by column chromatography on silica gel (PE:EA=15: 1) to give the title compound (6.0 g, 62percent) as a solid.
37%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃; for 2.25h;Inert atmosphere;	Step 1: A suspension of <strong>[33930-63-1]4-bromo-2-methylisoquinolin-1-one</strong> (100 mg, 0.42 mmol), bis(pinacolato)diboron (214 mg, 0.84 mmol), Pd(dppf)Cl2 (31 mg, 0.04 mmol) and potassium acetate (104 mg, 1.05 mmol) in dioxane (2 mL) under nitrogen was warmed up to 90° C. for 135 minutes. It was then cooled down to room temperature and diluted with ethyl acetate (8 mL). The mixture was washed with aqueous saturated solution of NaHCO3 (8 mL) and brine (8 mL). The organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by normal phase column chromatography (10-90percent EtOAc/Hexanes) to give the title compound (44 mg, 37percent). 1H NMR (CDCl3, 400 MHz) delta 8.43 (d, J=7.9 Hz, 1H), 8.40 (dd, J=8.2 Hz, 0.9 Hz, 1H), 7.68 (s, 1H), 7.65 (ddd, J=8.2, 8.2, 1.1 Hz, 1H), 7.46 (t, J=7.5 Hz, 1H), 3.63 (s, 3H), 1.38 (s, 12H). LCMS (M+H)+ 286.
	With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos; In 1,4-dioxane; at 60℃; for 8.0h;Inert atmosphere;	2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2H-isoquinolin-1-one S-1 4-Bromo-2-methyl-2H-isoquinolin-1-one Q-1 (0.550 g; 2.241 mmol), bispinacolatodiboron (1.250 g; 4.922 mmol), tris(dibenzylideneacetone)-dipalladium(0) (0.260 g; 0.275 mmol), XPHOS (0.310 g; 0.650 mmol) and potassium acetate (0.600 g; 6.114 mmol) are introduced in a round bottom flask. 1,4-dioxane (12 mL) is added and the flask is flushed with argon. The reaction mixture is stirred at 60° C. (Drysyn) for 8 h. The reaction mixture is then cooled to RT and filtered through a plug of celite. The filtrate is concentrated under reduced pressure. The residue is dissolved in DCM (100 mL) and washed with water (100.0 mL). The combined organic layer is dried with Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by silica gel chromatography Combiflash (Column Redisep Rf, 40 g; gradient: cyclohexane/EtOAc=100percent/0percent to 70percent/30percent over 13 column volumes; flow rate=40 mL/min; detection wavelength: 254 nm). The product containing fractions are combined and concentrated under reduced pressure. HPLC-MS: (M+H)+=286; tRet=1.483 min; method M7

References: [1]Patent: WO2016/172618,2016,A1 .Location in patent: Paragraph 0137.
[2]Patent: US2015/111885,2015,A1 .Location in patent: Paragraph 0540; 0541.
[3]Patent: US2018/44335,2018,A1 .Location in patent: Paragraph 0778-0779.

33
[ 33930-63-1 ]
[2,5-dimethoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine hydrochloride [ No CAS ]
4-{4-[(dimethylamino)methyl]-2,5-dimethoxyphenyl}-2-methyl-1,2-dihydroisoquinolin-1-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4462 - 4475.

34
[ 33930-63-1 ]
[2,6-dimethoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}dimethylamine hydrochloride [ No CAS ]
4-{4-[(dimethylamino)methyl]-3,5-dimethoxyphenyl}-2-methyl-1,2-dihydroisoquinolin-1-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4462 - 4475.

35
[ 3951-95-9 ]
[ 74-88-4 ]
[ 33930-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In tetrahydrofuran; at 20℃;	4-Bromo-2-methyl-2H-isoquinolin-1-one Q-1 To a suspension of 4-bromo-1(2H)-isoquinolinone P-1 (1.000 g; 4.240 mmol) and potassium carbonate (1.172 g; 8.480 mmol) in tetrahydrofuran (10.0 mL), iodomethane (0.423 mL; 6.664 mmol) are added. The reaction mixture is stirred overnight at RT. The reaction mixture is quenched with 10percent ammonia solution (30 mL) and water (50 mL) is added. THF is removed under reduced pressure. The precipitated product is filtered off and dried under reduced pressure. HPLC-MS: (M+H)+=238; tRet=1.02 min; method M1

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4462 - 4475.
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 379 - 384.
[3]Patent: US2018/44335,2018,A1 .Location in patent: Paragraph 0720-0721.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Chan-Lam Coupling Reaction • Complex Metal Hydride Reductions • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Preparation of Amines • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 33930-63-1 ]

Bromides

A148796 [3951-95-9]

4-Bromoisoquinolin-1(2H)-one

Similarity: 0.88

A447876 [190777-77-6]

5-Bromoisoquinolin-1(2H)-one

Similarity: 0.87

A184392 [864866-92-2]

6-Bromo-2-methylisoquinolin-1(2H)-one

Similarity: 0.85

A112157 [1227607-99-9]

4-Bromo-6-fluoroisoquinolin-1(2H)-one

Similarity: 0.82

A419422 [1028252-13-2]

4-Bromo-7-chloroisoquinolin-1(2H)-one

Similarity: 0.80

Amides

A148796 [3951-95-9]

4-Bromoisoquinolin-1(2H)-one

Similarity: 0.88

A447876 [190777-77-6]

5-Bromoisoquinolin-1(2H)-one

Similarity: 0.87

A184392 [864866-92-2]

6-Bromo-2-methylisoquinolin-1(2H)-one

Similarity: 0.85

A112157 [1227607-99-9]

4-Bromo-6-fluoroisoquinolin-1(2H)-one

Similarity: 0.82

A419422 [1028252-13-2]

4-Bromo-7-chloroisoquinolin-1(2H)-one

Similarity: 0.80

Related Parent Nucleus of
[ 33930-63-1 ]

Isoquinolines

A148796 [3951-95-9]

4-Bromoisoquinolin-1(2H)-one

Similarity: 0.88

A447876 [190777-77-6]

5-Bromoisoquinolin-1(2H)-one

Similarity: 0.87

A184392 [864866-92-2]

6-Bromo-2-methylisoquinolin-1(2H)-one

Similarity: 0.85

A112157 [1227607-99-9]

4-Bromo-6-fluoroisoquinolin-1(2H)-one

Similarity: 0.82

A419422 [1028252-13-2]

4-Bromo-7-chloroisoquinolin-1(2H)-one

Similarity: 0.80

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CAS No.: 33930-63-1

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