[ CAS No. 1532-71-4 ] {[proInfo.proName]}

Name: 1532-71-4|1-Bromoisoquinoline|97%
Brand: Ambeed
SKU: A112876
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Quality Control of [ 1532-71-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1532-71-4 ]

Product Details of [ 1532-71-4 ]

CAS No. :	1532-71-4	MDL No. :	MFCD00234478
Formula :	C₉H₆BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YWWZASFPWWPUBN-UHFFFAOYSA-N
M.W :	208.05	Pubchem ID :	640963
Synonyms :

Calculated chemistry of [ 1532-71-4 ]

Physicochemical Properties

Num. heavy atoms :	11
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 :	49.44
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	3.27
Log Po/w (WLOGP) :	3.0
Log Po/w (MLOGP) :	2.56
Log Po/w (SILICOS-IT) :	3.17
Consensus Log Po/w :	2.82

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.86
Solubility :	0.0285 mg/ml ; 0.000137 mol/l
Class :	Soluble
Log S (Ali) :	-3.22
Solubility :	0.127 mg/ml ; 0.000609 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.56
Solubility :	0.00574 mg/ml ; 0.0000276 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.62

Safety of [ 1532-71-4 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P280-P273-P301+P310-P305+P351+P338	UN#:	2923
Hazard Statements:	H301-H318-H401	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1532-71-4 ]

* 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.

Upstream synthesis route of [ 1532-71-4 ]
Downstream synthetic route of [ 1532-71-4 ]

[ 1532-71-4 ] Synthesis Path-Upstream 1~11

1
[ 1532-71-4 ]
[ 80278-67-7 ]

Reference： [1] Patent: US6645975, 2003, B1,

2
[ 1532-71-4 ]
[ 68-12-2 ]
[ 4494-18-2 ]

Reference： [1] ChemMedChem, 2016, vol. 11, # 4, p. 403 - 419

3
[ 1532-71-4 ]
[ 1532-84-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 4, p. 627 - 631

4
[ 1532-72-5 ]
[ 1532-71-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide In dichloromethane at 0 - 25℃; for 6 h; Inert atmosphere	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH₂Cl₂ (0.1 M) at 0 °C is added POBr₃ (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7–8. The resulting mixture is separated and the aqueous phase is extracted with CH₂Cl₂ thoroughly. The organic phase is combined and washed with brine, dried over Na₂SO₄, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

Reference： [1] Organic Letters, 2015, vol. 17, # 12, p. 2948 - 2951
[2] Organic Letters, 2013, vol. 15, # 4, p. 792 - 795
[3] Tetrahedron, 2016, vol. 72, # 38, p. 5762 - 5768
[4] Organic Letters, 2016, vol. 18, # 9, p. 1956 - 1959

5
[ 4594-71-2 ]
[ 1532-71-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With dibromoisocyanuric acid; triphenylphosphine In neat (no solvent) at 160 - 170℃; for 17 h; Inert atmosphere	General procedure: Ina flask (50 mL) equipped with a magnetic stirrer bar and a balloon, a mixture of triphenylphosphine (1186mg, 4.52 mmol) and dibromoisocyanuric acid (652 mg, 2.27 mmol) was heated under an argonatmosphere. Dibromoisocyanuric acid vigorously reacted at 115 °C, and the mixture heated for anadditional 10 min. 1-Methylquinolin-2(1H)-one (239 mg, 1.50 mmol) was added to the mixture, whichwas heated at 160-170 °C for 16 h. Then, the reaction mixture was dissolved in CH2Cl2 and basified withtriethylamine, followed by separation using silica gel column chromatography. The use of hexane-EtOAc(6:1) as an eluate resulted in isolation of 2-bromoquinoline (244 mg, 78percent).

Reference： [1] Heterocycles, 2015, vol. 91, # 7, p. 1445 - 1454

6
[ 491-30-5 ]
[ 1532-71-4 ]

Reference： [1] Yakugaku Zasshi, 1931, vol. 51, p. 542,571; dtsch. Ref. S. 73, 76[2] Chem.Abstr., 1931, p. 5427
[3] Recueil des Travaux Chimiques des Pays-Bas, 1943, vol. 62, p. 466
[4] Patent: EP446604, 1991, A2,

7
[ 19493-44-8 ]
[ 1532-71-4 ]

Reference： [1] European Journal of Organic Chemistry, 2002, # 24, p. 4181 - 4184

8
[ 119-65-3 ]
[ 1532-71-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 699,706
[2] Heterocycles, 2015, vol. 91, # 7, p. 1445 - 1454

9
[ 119-65-3 ]
[ 7726-95-6 ]
[ 1532-71-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1937, vol. 56, p. 699,706

10
[ 1532-71-4 ]
[ 51206-40-7 ]

Reference： [1] Patent: US4678781, 1987, A,

11
[ 1532-71-4 ]
[ 1066-54-2 ]
[ 86520-96-9 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5477 - 5481[2] Angew. Chem., 2018, vol. 130, p. 5575 - 5579,5

[ 1532-71-4 ] Synthesis Path-Downstream 1~88

1
[ 119-65-3 ]
[ 1532-71-4 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1937,vol. 56,p. 699,706
[2]Heterocycles,2015,vol. 91,p. 1445 - 1454

2
[ 491-30-5 ]
[ 1532-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus tribromide;	Example 13 1-Bromoisoquinoline A mixture of 9.0 g of 1-hydroxyisoquinoline and 40 ml of phosphorus tribromide is inserted for 15 minutes into a preheated oil bath at 135oC. The resulting 2 layers are cooled and concentrated in vacuo. The residue is treated with ice, water, and sodium carbonate. The reaction mixture is extracted with chloroform, dried over sodium sulfate and concentrated. The product is purified by column chromatography, yielding 6.8 g of pale yellow crystals, mp 41-43oC.

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1931,vol. 51,p. 542,571; dtsch. Ref. S. 73, 76
Chem.Abstr.,1931,p. 5427
[2]Patent: EP446604,1991,A2

3
[ 1532-71-4 ]
[ 502-42-1 ]
[ 90380-72-6 ]

Reference： [1]Synthesis,1984,p. 161 - 164

4
[ 1532-71-4 ]
[ 90380-77-1 ]

Reference： [1]Synthesis,1984,p. 161 - 164

5
[ 1532-71-4 ]
[ 90380-77-1 ]

Reference： [1]Synthesis,1984,p. 161 - 164

6
[ 1532-71-4 ]
[ 102047-50-7 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 565

7
[ 1532-71-4 ]
[ 5467-92-5 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 565

8
[ 1532-71-4 ]
[ 375853-82-0 ]
[ 871836-40-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 80℃; for 18h;	A solution of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> (0.35 g, 1.68 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (US 2004/0186103) (0.5 g, 1.68 mmol), dichloro(1,1-bis(diphenylphosphino)ferrocene)palladium(II) (0.065 g, 0.05 mol equiv.) and potassium carbonate (0.66 g, 5.0 mmol) in 1,2-dimethoxyethane (10 mL) was heated at 80 °C for 18 hours. The reaction mixture was allowed to cool and then evaporated under reduced pressure. The residue was purified' by column chromatography on silica gel eluting with ethyl acetate: pentane 50 : 50 to afford the title compound as a pale yellow oil, 0.14 g. LRMS (APCI+): m/z [M+H]+ 311

Reference： [1]Patent: WO2005/121094,2005,A1 .Location in patent: Page/Page column 46

9
[ 1532-71-4 ]
[ 5720-06-9 ]
[ 134948-96-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; N,N-dimethyl-formamide; at 50℃; for 12h;	Stage A: 1 -(2-methoxyphenyl)isoquinoline.A solution of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> (2.06 g, 10 mmol), prepared as described in EuropeanJournal of Organic Chemistry 2002, 4181-4184, 2-methoxyphenylboronic acid (2.79 g, 10 mmol), Pd(PPh3)4 (5percentmol), K2CO3 (5g) in DMF/water (3/1) is stirred at 500C for 12 hours.The reaction mixture is then pored on water (150 mL). The aqueous phase is extracted with EPO <DP n="84"/>ethyl acetate (3xl00mL). The combined organic layers are washed with water (3x200mL).The organic phase is dried over magnesium sulfate and evaporated under vacuum to afford the title compound.

Reference： [1]Patent: WO2006/103120,2006,A2 .Location in patent: Page/Page column 82-83

10
[ 1532-71-4 ]
[ 420-37-1 ]
1-bromo-2-methylisoquinolinium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane;	2. The starting material was prepared by reaction of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> with trimethyloxonium tetrafluoroborate in CH2 Cl2 to give 1-bromo-2-methylisoquinolinium tetrafluoroborate, m.p. 162°.

Reference： [1]Patent: US4678781,1987,A

11
[ 1532-71-4 ]
[ 51206-40-7 ]
1,4-dibromo-2-methylisoquinolinium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide;	5. The starting material was prepared by reaction of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> with HBr to give 1,4-di<strong>[1532-71-4]bromoisoquinoline</strong>, m.p. 95°-96°, followed by reaction of this compound with trimethyloxonium tetrafluoroborate in CH2 Cl2 to give 1,4-dibromo-2-methylisoquinolinium tetrafluoroborate; n.m.r. in solvent A: 3.5(s, 3H); 7.2-8.4(m, 5H).

Reference： [1]Patent: US4678781,1987,A

12
[ 1532-71-4 ]
[ 96630-53-4 ]

Yield	Reaction Conditions	Operation in experiment
	In concentrated H2 SO4;	8. The starting material was prepared by reaction of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> in concentrated H2 SO4 at 0° with KNO3. The reaction mixture was worked up with water, NaHCO3 and EtOAc to give 1-bromo-5-nitro isoquinoline, m.p. 187°-8°.

Reference： [1]Patent: US4678781,1987,A

13
[ 1445-73-4 ]
[ 1532-71-4 ]
isoquinolyl-1-lithium [ No CAS ]
lithium 1-methyl-4-(1-isoquinolyl)-piperidin-4-olate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water;	EXAMPLE 12 A solution of 11.3 g. of 1-methylpiperidin-4-one in 120 ml. of ether is added dropwise to a stirred isoquinolyl-1-lithium solution, freshly prepared from 20.8 g. of <strong>[1532-71-4]1-<strong>[1532-71-4]bromoisoquinoline</strong></strong> and n-butyllithium in 400 ml. of ether, at 0°, under dry nitrogen. The mixture is stirred for 2 hours more at 0°. Water (50 ml.) and then 100 ml. of 5percent hydrochloric acid are added dropwise to decompose the lithium 1-methyl-4-(1-isoquinolyl)-piperidin-4-olate formed.

Reference： [1]Patent: US4122180,1978,A

14
[ 1532-71-4 ]
[ 868286-21-9 ]
[ 267417-04-9 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 424 - 433

15
[ 1532-71-4 ]
[ 17997-47-6 ]
[ 56076-42-7 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 424 - 433

16
[ 1532-71-4 ]
[ 189195-41-3 ]
[ 1204521-26-5 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 424 - 433

17
[ 1532-71-4 ]
[ 394-65-0 ]

Reference： [1]Synthesis,2010,p. 2490 - 2494

18
[ 1532-71-4 ]
[ 98-80-6 ]
[ 3297-72-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; at 80℃; for 24h;	Place 2-<strong>[1532-71-4]bromoisoquinoline</strong> (20 g, 1 eq) in a dry 1000 ml two-necked flask.Phenylboronic acid (12.3 g, 1.05 eq), Pd (PPh3) 4 (5.55 g, 0.05 eq)And sodium carbonate (30.5 g, 3 eq), then dioxane (500 mL),The reaction was heated to 80 C and stirred for one day.Then, the reaction solution was spun dry, separated into water and dichloromethane, and the organic phase was dried.Purification by column to obtain white intermediate C(Yield 96%).
79%	With potassium phosphate; In ethanol; water; at 100℃; for 8h;	General procedure: A dried round bottomed flask equipped with a magnetic stirring bar was charged with 10mg Polymer anchored-Pd(II) D catalyst (PS-NPPZ-Pd) (0.0045mmol/Pd), 2-halopyridine (0.5mmol), phenylboronic acid (0.6mmol) and K3PO4 (1.0mmol) were added to a reaction vessel. The mixture was stirred in 4mL of H2O: EtOH (1:1) at 100C for 8h and then cooled to room temperature. The catalyst was filtered and the filtrate was extracted with ethyl acetate (3×10mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethyl acetate/hexane (10:90) as eluent to give the corresponding coupled products. The products were characterized by 1H NMR, 13C NMR and HRMS analysis.

Reference： [1]Patent: CN109608481,2019,A .Location in patent: Paragraph 0266; 0267; 0268; 0269
[2]Inorganica Chimica Acta,2018,vol. 477,p. 227 - 232
[3]Journal of the American Chemical Society,2010,vol. 132,p. 10272 - 10274
[4]New Journal of Chemistry,2015,vol. 39,p. 5259 - 5264
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 10975 - 10979
Angew. Chem.,2015,vol. 127,p. 11126 - 11130,5
[6]Chemical Communications,2018,vol. 54,p. 8202 - 8205
[7]Organic Letters,2019,vol. 21,p. 3735 - 3740
[8]Angewandte Chemie - International Edition,2019,vol. 58,p. 15244 - 15248
Angew. Chem.,2019,vol. 131,p. 15388 - 15392,5

19
[ 1532-71-4 ]
[ 108-95-2 ]
[ 69716-18-3 ]

Reference： [1]Organometallics,2010,vol. 29,p. 4058 - 4065

20
[ 1532-71-4 ]
[ 52670-38-9 ]
[ 1323111-15-4 ]

Reference： [1]Synthesis,2011,p. 1723 - 1732

21
[ 1532-71-4 ]
[ 52670-38-9 ]
[ 1323111-68-7 ]

Reference： [1]Synthesis,2011,p. 1723 - 1732

22
[ 1532-71-4 ]
[ 66947-60-2 ]
CF₃O₃S^(1-)*C₂₁H₂₀NO₃⁽¹⁺⁾ [ No CAS ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 612 - 613

23
[ 1532-71-4 ]
[ 66947-60-2 ]
[ 108-24-7 ]
C₂₀H₁₇NO₃ [ No CAS ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 612 - 613

24
[ 1532-71-4 ]
[ 1332329-61-9 ]
[ 1332328-59-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene;Inert atmosphere; Reflux;	Example 116-(5-(isoquinolin- 1 -ylamino)-2-methylphenyl)-2-(4-(4-methylpiperazin- 1 - ynphenylamino -7.8-dihydropyrido[4.3-dlpyrimidin-5(6H -oneA mixture of 2,2'-Bis(diphenylphosphino)l,r-binaphthyl [BINAP] (28.00 mg, 0.0451 mmol) and Palladium(II)acetate [Pd(OAc)2] (5.00 mg,0.022 mmol) in dry toluene (3ml) was stirred vigorously and nitrogen was bubbled through the suspension for 30 minutes. To this, 6-(5-amino-2-methylphenyl)-2-(4-(4- methylpiperazin- l-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)- one [45](200 mg, 0.451 mmol), 1 -<strong>[1532-71-4]bromoisoquinoline</strong> (1 12.60 mg, 0.541 mmol) and dry cesium carbonate (443.0 mg, 1.352mmol) was added. Nitrogen was bubbled through for another 30 minutes; the mixture was allowed to 15 reflux overnight. The mixture was cooled, diluted with ethyl acetate, water was added and the layers separated. The aqueous layer was extracted with ethyl acetate and the two organic extracts were combined. The organics were washed with brine, then dried (sodiumsulfate), filtered and concentrated. Further purification by silica gel chromatography using 5-10percent ethyl acetate / hexane as eluent provided 6-(5-(isoquinolin- 1 -ylamino)-2-methylphenyl)-2-(4-(4-methylpiperazin- 1 - yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one [60] as a yellow solid [Yield:-223 mg, 87.0percent].

Reference： [1]Patent: WO2011/101806,2011,A1 .Location in patent: Page/Page column 110-111

25
[ 1532-71-4 ]
[ 62-53-3 ]
[ 1352932-50-3 ]
[ 1352932-52-5 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 13613 - 13620

26
[ 1532-71-4 ]
[ 62-53-3 ]
[ 13797-20-1 ]

Reference： [1]Chemistry - A European Journal,2011,vol. 17,p. 13613 - 13620
[2]Chemical Communications,2013,vol. 49,p. 7352 - 7354

27
[ 1532-71-4 ]
[ 1461-22-9 ]
[ 884658-29-1 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of (S)-2-(l-(2-Butyl-8-fluoroquinolin-3-yl)ethyl)isoindoline-l,3- dione:The reagent l-(tributylstannyl)isoquinoline was made as follows: A solution of 1- <strong>[1532-71-4]bromoisoquinoline</strong> (2100 mg, 10094 muiotaetaomicron) in 100 mL of anyhdrous THF was cooled to -78 °C. To this solution was added 2.5 n-BuLi in hexanes (4239 mu, 10598 muiotaetaomicron). After 15 minutes, the reaction was treated with tributyltin chloride (2875 mu,, 10598 muiotaetaomicron) and allowed to warm to rt. The reaction was quenched with 50percent sat. NH4C1 and extracted with ether. The organic phase was washed with brine and concentrated. The crude material was purified by column chromatography to afford impure l-(tributylstannyl)isoquinoline, used as is in the following reaction. A reaction flask containing tetrakis triphenylphosphine- palladium(O) (115 mg, 100 muiotaetaomicron), l-(tributylstannyl)isoquinoline (835 mg, 1996 muiotaetaomicron), and (S)-2-(l-(2-chloro-8-fluoroquinolin-3-yl)ethyl)isoindoline-l,3-dione (354 mg, 998 muiotaetaomicron) was fitted with areflux condensor and a septum. The reaction was purged with N2 and then argon. To the flask was added 1 ,4-dioxane (8315 mu,, 998 muiotaetaomicron) and the reaction was heated to 100 °C for 3 days. Concentration and purification by column chromatography using 10percent ethyl acetate in hexanes afforded (S)-2-(l-(2-butyl-8-fluoroquinolin-3-yl)ethyl)isoindoline-l,3- dione. LC/MS (M+H) = 377.0. 1H-NMR (400 MHz, CDC13) delta 8.60 (s, 1H), 7.82 (m, 2H), 7.72 (m, 2H), 7.65 (d, J = 8.2 Hz, 1H), 7.41 (td, J = 7.8, 5.1 Hz, 1H), 7.35 (ddd, J = 10.8, 7.8, 1.4 Hz, 1H), 5.93 (q, J = 7.2 Hz, 1H), 3.16 (ddd, J = 13.7, 10.8, 5.7 Hz, 1H), 3.00 (ddd, J = 13.5, 10.8, 5.4 Hz, 1H), 2.00 (d, J = 7.0 Hz, 3H), 1.84-1.61 (series of m, 2H), 1.60-1.30 (series of m, 4H), 0.90 (t, J = 7.4 Hz, lH) ppm. (S)-2-(l-(7-Fluoro-2-(2-methylbutyl)quinolin-3-yl)ethyl)isoindoline-l,3-dione -2-(l-(2-benzyl-7-fluoroquinolin-3-yl)ethyl)isoindoline-l,3-dione:

Reference： [1]Patent: WO2012/3271,2012,A1 .Location in patent: Page/Page column 38

28
[ 1532-71-4 ]
[ 555-57-7 ]
C₂₀H₁₈N₂ [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 2373 - 2379

29
[ 1532-72-5 ]
[ 1532-71-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With N,N-dimethyl-formamide; phosphorus(V) oxybromide; In dichloromethane; at 0 - 25℃; for 6h;Inert atmosphere;	General procedure: To a stirred solution of the appropriate azine N-oxides in anhydrous CH2Cl2 (0.1 M) at 0 °C is added POBr3 (1.2 equiv) followed by dropwise addition of DMF (0.5 equiv) under argon. The resulting reaction mixture was warmed to 25 °C and stirred for several hours until the reaction is complete as indicated by TLC. Saturated aqueous sodium carbonate solution is added to the reaction mixture slowly to adjust the pH to 7?8. The resulting mixture is separated and the aqueous phase is extracted with CH2Cl2 thoroughly. The organic phase is combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude product, which is purified by flash column chromatography using PE/EA (100:1) as eluent.

Reference： [1]Organic Letters,2015,vol. 17,p. 2948 - 2951
[2]Organic Letters,2013,vol. 15,p. 792 - 795
[3]Tetrahedron,2016,vol. 72,p. 5762 - 5768
[4]Organic Letters,2016,vol. 18,p. 1956 - 1959

30
[ 1532-71-4 ]
[ 1532-84-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2013,vol. 355,p. 627 - 631

31
[ 1532-71-4 ]
[ 62-53-3 ]
[ 239-44-1 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 7352 - 7354

32
[ 1532-71-4 ]
[ 201230-82-2 ]
[ 28144-70-9 ]
2-(isoquinolin-1-yl)quinazolin-4(3H)-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12635 - 12638

33
[ 865245-32-5 ]
[ 1532-71-4 ]
C₁₉H₂₂N₂O₂ [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 413 - 415

34
[ 865245-32-5 ]
[ 1532-71-4 ]
[ 1526912-90-2 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 413 - 415

35
[ 110-91-8 ]
[ 1532-71-4 ]
[ 883794-85-2 ]