[ CAS No. 215453-51-3 ] {[proInfo.proName]}

Name: 215453-51-3|7-Bromo-1-chloroisoquinoline|97%
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Quality Control of [ 215453-51-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 215453-51-3 ]

Product Details of [ 215453-51-3 ]

CAS No. :	215453-51-3	MDL No. :	MFCD04039320
Formula :	C₉H₅BrClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UMSWWSIVPWVJOX-UHFFFAOYSA-N
M.W :	242.50	Pubchem ID :	6502024
Synonyms :

Calculated chemistry of [ 215453-51-3 ]

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 Å²

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) :	3.12
Log Po/w (SILICOS-IT) :	3.76
Consensus Log Po/w :	3.32

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 [ 215453-51-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362+P364-P403+P233-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 215453-51-3 ]

* 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 [ 215453-51-3 ]
Downstream synthetic route of [ 215453-51-3 ]

[ 215453-51-3 ] Synthesis Path-Upstream 1~8

1
[ 223671-15-6 ]
[ 215453-51-3 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 8, p. 913 - 918
[2] Patent: WO2004/828, 2003, A1,
[3] Patent: WO2005/120509, 2005, A1, . Location in patent: Page/Page column 69-70

2
[ 223671-15-6 ]
[ 215453-51-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537
[2] Synthetic Communications, 2005, vol. 35, # 5, p. 725 - 730
[3] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 18, p. 2753 - 2758
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2341 - 2351
[5] Patent: US2002/45613, 2002, A1,

3
[ 34551-41-2 ]
[ 215453-51-3 ]

Reference： [1] Patent: US6248738, 2001, B1,

4
[ 1200-07-3 ]
[ 215453-51-3 ]

Reference： [1] Synthetic Communications, 2005, vol. 35, # 5, p. 725 - 730
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537

5
[ 27465-66-3 ]
[ 215453-51-3 ]

Reference： [1] Synthetic Communications, 2005, vol. 35, # 5, p. 725 - 730

6
[ 1122-91-4 ]
[ 215453-51-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 14, p. 5522 - 5537

7
[ 215453-51-3 ]
[ 215453-53-5 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 8, p. 913 - 918
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 19, p. 2837 - 2842

8
[ 215453-51-3 ]
[ 223671-15-6 ]

Yield	Reaction Conditions	Operation in experiment
2.7 g	at 100℃; for 4 h;	To a solution of 7-bromo-1-chloroisoquinoline 1a (2.70 g, 11.10 mmol) in acetic acid (50 mL) was addedammonium acetate 1b (8.50 g, 111.10 mmol). Reaction mixture was stirred at 100°C for 4 h. The reaction mixture wasconcentrated in vacuo, and to the residue was added water. The precipitate was collected by filtration and washed withwater to give 7-bromoisoquinolin-1(2H)-one 1c (2.7 g, white solid). The product was used in the next step directly withoutpurification.MS m/z (ESI): 225.9 [M+1]1H NMR (400 MHz, CDCl3) δ 8.55 (d, J = 1.8 Hz, 1H), 7.75 (dd, J = 2.1, 8.5 Hz, 1H), 7.43 (d, J = 8.6 Hz, 1H), 7.14 (d,J = 6.2 Hz, 1H), 6.52 (d, J = 7.3 Hz, 1H)

Reference： [1] Chemical Communications, 2018, vol. 54, # 75, p. 10574 - 10577
[2] Patent: EP3042907, 2016, A1, . Location in patent: Paragraph 0324; 0325

[ 215453-51-3 ] Synthesis Path-Downstream 1~88

1
[ 215453-51-3 ]
[ 4114-31-2 ]
[ 953421-68-6 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; at 170℃; for 0.666667h;Microwave irradiation;	<strong>[215453-51-3]7-Bromo-1-chloroisoquinoline</strong> (1-1) (79 mg, 0.327 mmol, 1.0 equiv) and Ethyl carbazate (34 mg, 0.33 mmol, 1.0 equiv) were suspended in EtOH (1.5 mL). The reaction mixture was irradiated in microwave at 170 C. for 40 minutes. The crude mixture was purified with reverse phase HPLC (H2O/CH3CN gradient w/0.1% TFA present) to yield 9-bromo[1,2,4]triazolo[3,4-a]isoquinolin-3(2H)-one (1-2). LRMS m/z (M+H) 263.9 and 264.9 found, 264.1 and 265.1 required.

Reference： [1]Patent: US2007/254879,2007,A1 .Location in patent: Page/Page column 25

2
[ 215453-51-3 ]
[ 223671-78-1 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2341 - 2351

3
[ 215453-51-3 ]
C₁₀H₁₁N₅O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2341 - 2351

4
[ 215453-51-3 ]
[ 223671-79-2 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2341 - 2351

5
[ 215453-51-3 ]
C₁₆H₁₅N₅O₂S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2341 - 2351

6
[ 1200-07-3 ]
[ 215453-51-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

7
[ 27465-66-3 ]
[ 215453-51-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730

8
(E)-3-(4-bromophenyl)acryloyl azide [ No CAS ]
[ 215453-51-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

9
[ 215453-51-3 ]
7-piperidin-4-yl-isoquinolin-1-ylamine [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730

10
[ 215453-51-3 ]
[ 852332-83-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730

11
[ 215453-51-3 ]
[ 852332-82-2 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730

12
1-Bromo-4-((E)-2-isocyanato-vinyl)-benzene [ No CAS ]
[ 215453-51-3 ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 725 - 730

13
[ 215453-51-3 ]
[ 223671-64-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

14
[ 215453-51-3 ]
[ 223671-62-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

15
[ 215453-51-3 ]
N-(7-hydroxymethyl-isoquinolin-1-yl)-guanidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

16
[ 215453-51-3 ]
N-[7-(1-hydroxy-ethyl)-isoquinolin-1-yl]-guanidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

17
[ 215453-51-3 ]
1-guanidino-isoquinoline-7-carboxylic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

18
[ 215453-51-3 ]
N-(7-phenyl-isoquinolin-1-yl)-guanidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

19
[ 215453-51-3 ]
N-(7-benzo[1,3]dioxol-5-yl-isoquinolin-1-yl)-guanidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3227 - 3230

20
[ 215453-51-3 ]
[ 252970-88-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

21
[ 215453-51-3 ]
[ 215453-54-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

22
[ 215453-51-3 ]
N-(7-Formylisoquinolinyl)benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

23
[ 215453-51-3 ]
[ 252970-73-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

24
[ 215453-51-3 ]
[ 862845-69-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

25
[ 215453-51-3 ]
[ 215453-55-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

26
[ 215453-51-3 ]
methanesulfonic acid 1-benzoylamino-isoquinolin-7-ylmethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

27
[ 215453-51-3 ]
[ 252971-01-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

28
[ 215453-51-3 ]
2-amino-3-(1-amino-isoquinolin-7-yl)-1-(4-methyl-piperidin-1-yl)-propan-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

29
[ 215453-51-3 ]
1-Chloro-isoquinoline-7-sulfonic acid [(S)-1-(3-cyano-benzyl)-pyrrolidin-3-yl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

30
[ 215453-51-3 ]
3-[(S)-3-(Isoquinoline-7-sulfonylamino)-pyrrolidin-1-ylmethyl]-benzamidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

31
[ 215453-51-3 ]
[ 252971-37-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

32
[ 215453-51-3 ]
1-Amino-isoquinoline-7-sulfonic acid [(S)-1-(3-cyano-benzyl)-pyrrolidin-3-yl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

33
[ 215453-51-3 ]
[ 252971-80-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

34
[ 215453-51-3 ]
3-(1-amino-isoquinolin-7-yl)-2-(7-methoxy-naphthalene-2-sulfonylamino)-propionic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

35
[ 215453-51-3 ]
3-[(S)-3-(1-Chloro-isoquinoline-7-sulfonylamino)-pyrrolidin-1-ylmethyl]-benzimidic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

36
[ 215453-51-3 ]
3-[(S)-3-(1-Chloro-isoquinoline-7-sulfonylamino)-pyrrolidin-1-ylmethyl]-benzamidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

37
[ 215453-51-3 ]
3-[(S)-3-(1-Amino-isoquinoline-7-sulfonylamino)-pyrrolidin-1-ylmethyl]-benzamidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

38
[ 215453-51-3 ]
3-[(S)-3-(1-Amino-isoquinoline-7-sulfonylamino)-pyrrolidin-1-ylmethyl]-benzimidic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

39
[ 215453-51-3 ]
1-Phenoxy-isoquinoline-7-sulfonic acid [(S)-1-(3-cyano-benzyl)-pyrrolidin-3-yl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2753 - 2758

40
[ 215453-51-3 ]
[ 215453-56-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

41
[ 215453-51-3 ]
7-methoxy-naphthalene-2-sulfonic acid [1-(1-amino-isoquinolin-7-ylmethyl)-2-(4-methyl-piperidin-1-yl)-2-oxo-ethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842
[2]Bioorganic and Medicinal Chemistry Letters,1999,vol. 9,p. 2837 - 2842

42
[ 215453-51-3 ]
[ 57260-71-6 ]
[ 636998-09-9 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium carbonate; In dimethyl sulfoxide; at 20 - 110℃; for 24h;	INTERMEDIATE 10 [4- (7-BROMO-ISOQUINOLINE-1-YL)-PIPERAZINE-1-CARBOXYLIC] acid, [TERT-BUTYL] ester To a suspension [OF 7-BROMO-1-CHLOROISOQUINOLINE] (3.14 g, 1 3 mmol) in DMSO (20 mL) at room temperature was added either carboxylic acid tert-butyl (BOC) piperazine (7.23 g, [38.] 8 mmol) or BOC-homopiperazine (7.77 g, [38.] 8 mmol) and then potassium carbonate (5. [36] g, [39] mmol). The mixture was heated to [110 C] for 24 h. On cooling, the mixture was poured onto ice/water (50 mL) and extracted with ethyl acetate (3 x 50 mL). The combined organic phases were washed with water 50 mL) and brine (50 mL). Before drying over anhydrous sodium sulfate. Removal of solvent under reduced pressure gave crude product. Purification was performed by applying the crude material to a plug of silica in a filter funnel and eluting with heptane/ethyl acetate (2: 1) and gave 2.73 g (54 %) yellow [OIL.'H] NMR [(CDC13) 6] 8.20-8. 22 [(M,] 1 H), 8.13-8. 18 (d, J= 6 Hz, 1 H), 7.65-7-71 (dd, [J=] 12,3 Hz, 1 H), 7. [59-7.] 65 (d, [J = 12] Hz, 1 H), 7.21-7. 25 [(M,] [1] H), 3.64-3. 73 [(M,] 4 H), 7.27-7. 36 [(M,] 4 H), 1.49 (s, 9 H); LCMS: 392,394, 395.

Reference： [1]Patent: WO2004/828,2003,A1

43
[ 223671-15-6 ]
[ 215453-51-3 ]

Yield	Reaction Conditions	Operation in experiment
		INTERMEDIATE 9 7-Bromo-1-Chloroisoquinoline To phosphorus oxychloride (46.6 mL, 0.5 mol) at room temperature was added, portionwise, [7-BROMO-1-HYDROXYISOQUINOLINE] (11.2 g, 0.05 mol). The mixture was heated to [100 C] for 90 min with rapid stirring. On cooling to room temperature, the mixture was poured, cautiously onto ice/water (200 mL). Dropwise addition of aqueous ammonia raised the pH=8 and the resulting precipitate was collected by filtration, washing with cold water. The solid was dried under reduced vacuum at [45 C] for 12 h. 13.86 g (115 %) Beige solid [ISOLATED.'H] NMR (DMSO-d6) 8 8.4 (s, 1 H), 8.34-8. 38 (d, J = 6 Hz, 1 H), 8.03-8. 07 (m, 2 H), 7.91-7. 96 (d, J = 6 Hz, 1 H); HPLC : 96%; LCMS: 242,244, 246.
		Example 5; Synthesis of (109); Step A; Synthesis of (110); [0186] A mixture of 7-bromo-1-hydroxyisoquinoline (1 g, 4.47 mmol) and phosphorus oxychloride (20 mL) was heated at reflux for 20 min, cooled to room temperature, and concentrated in vacuo. The residue was treated with ice (100 g) and adjusted to pH 7 with 0.5M aqueous NaOH. The resulting mixture was extracted with EtOAc. The combined organic phases were washed with brine, dried over MgS04, and concentrated. The residue was crystallized from EtOAc/hexane to provide 110 (865 mg, 80%) as an off-white powder.

Reference： [1]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 913 - 918
[2]Patent: WO2004/828,2003,A1
[3]Patent: WO2005/120509,2005,A1 .Location in patent: Page/Page column 69-70

44
[ 215453-51-3 ]
[ 370864-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; triethylamine; In tetrahydrofuran; hydrogenchloride;	D. 1-Chloroisoquinolin-7-yl boronic acid <strong>[215453-51-3]7-Bromo-1-chloroisoquinoline</strong> (1.38 g, 5.69 mmol) in THF (15 mL) under nitrogen, at -78 C. and triisopropyl borate (2.99 g, 15.93 mmol) added, followed by dropwise addition of n-butyllithium (7.11 mL of 1.6M in hexanes, 11.38 mmol). Allowed reaction mixture to warm to -20 C. over 30 minutes and quenched with IN HCl (30 mL). Added triethylamine to give pH 7, presorbed solution directly onto silica and flash column chromatography on silica gel to give the product as pale yellow solid (0.78 g, 3.8 mmol). 1H NMR (DMSO) delta 8.73 (s, 1H), 8.48 (br s, 2H), 8.35-8.28 (m, 1H), 8.25-8.13 (m, 1H), 8.06-7.92 (m, 1H), 7.91-7.82 (m, 1H). ESI MS (M+i)+:208,210 (Cl).

Reference： [1]Patent: US2002/45613,2002,A1

45
7-Bromoisoquinoline N-oxide hydrochloride [ No CAS ]
[ 215453-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dichloromethane; water; ethyl acetate; trichlorophosphate;	Part C. 7-Bromo-1-chloroisoquinoline This compound was prepared by a procedure analogous to that for 6-bromo-1-chloroisoquinoline as in PCT WO 98/47876. A solution of 8.07 g (31 mmol) of the mixture from Part B was taken up in 50 mL of POCl3, and the mixture was heated at 90 C. for 2 hr. The reaction mixture was concentrated to remove most of the POCl3, and the residue was taken up in 100 mL of CH2Cl2. The solution was carefully basified to pH 10 by the slow addition of 1N NaOH, and the organic layer was washed with 100 mL of H2O, 100 mL of sat. NaCl, and dried over MgSO4. Filtration and concentration gave a light yellow solid, which was subjected to flash column chromatography on silica gel first with 5% and then with 10% EtOAc in hexanes. A total of 3.62 g (48%) of the desired 7-bromo-1-chloroisoquinoline was isolated from this chromatography free of the 5-bromo isomer.

Reference： [1]Patent: US6399627,2002,B1

46
[ 215453-51-3 ]
[ 215453-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; sodium hydroxide; In dichloromethane; water; phenol;	Part D. 7-Bromo-1-phenoxyisoquinoline A solution of 3.60 g (14.8 mmol) of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> and 1.5 g of solid KOH in 11.2 g of phenol was heated at 140 C. for 2 hr. The reaction was cooled to room temperature, then partitioned between 100 mL of CH2Cl2 and 100 mL of 3N NaOH. The organic layer was washed with another 2*100 mL of 3N NaOH, then with 100 mL of H2O, and dried over MgSO4. Filtration and concentration gave a yellow oil, which was subjected to flash column chromatography on silica gel 30% CH2Cl2 in hexanes, giving 3.42 g (77%) of the desired product as a light yellow solid.
	With potassium hydroxide; sodium hydroxide; In dichloromethane; water; phenol;	Part 4. 7-Bromo-1-phenoxyisoquinoline A solution of 3.60 g (14.8 mmol) of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> and 1.5 g of solid KOH in 11.2 g of phenol was heated at 140 C. for 2 hr. The reaction was cooled to room temperature, then partitioned between 100 mL of CH2Cl2 and 100 mL of 3N NaOH. The organic layer was washed with another 2*100 mL of 3N NaOH, then with 100 mL of H2O, and dried over MgSO4. Filtration and concentration gave a yellow oil, which was subjected to flash column chromatography on silica gel 30% CH2Cl2 in hexanes, giving 3.42 g (77%) of the desired product as a light yellow solid.

Reference： [1]Patent: US6399627,2002,B1
[2]Patent: US6534535,2003,B1

Yield	Reaction Conditions	Operation in experiment
		37b. 7-Bromo-1-chloroisoquinoline Compound 37b was prepared from 37a using the procedure described for 1b. 1H-NMR 200 MHz (CDCl3) delta: 7.57-7.88 (3H, m), 8.32 (1H, d, J=6 Hz), 8.51-8.54 (1H, m).

48
[ 109-72-8 ]
hexanes-EtOAc [ No CAS ]
[ 215453-51-3 ]
[ 223671-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With SO2Cl2; triethylamine; aniline; In THF-ether; hexane; dichloromethane;	Preparation 66 1-Chloro-7-phenylsulphamoylisoquinoline n-Butyllithium (0.88 mL, 2.5 M in hexanes, 2.2 mmol) was added dropwise to a stirred solution of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (500 mg, 2.06 mmol) in THF-ether (10 mL, 1:1) under N2 at -78 C. After 5 min, the mixture was added to a solution of SO2Cl2 (0.35 mL, 4.36 mmol) in hexane (10 mL) at -25 C. under N2, the mixture was warmed to 23 C. and stirred for 4.5 h. The solvents were evaporated in vacuo, azeotroping with PhMe, the residue was suspended in CH2Cl2 (12 mL) and then aniline (0.25 mL, 2.74 mmol) and NEt3 (1.15 mL, 8.25 mmol) were added. The mixture was stirred at room temperature overnight, washed with aqueous HCl (2 M), brine, and then evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (80:20 to 50:50) as eluant to give the title compound (116 mg, 0.36 mmol) as an off-white solid. 1H (CD3OD, 400 MHz) delta7.0-7.15 (3H, m), 7.2-7.25 (2H, m), 7.8 (1H, d), 8.1 (2H, 2*d), 8.4 (1H, d), 8.7 (1H, s) ppm. LRMS 319, 321 (MH+).

Reference： [1]Patent: US6248738,2001,B1

49
[ 109-72-8 ]
hexanes-EtOAc [ No CAS ]
sulphuryl chloride (SO₂Cl₂) [ No CAS ]
[ 215453-51-3 ]
[ 223671-78-1 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In tetrahydrofuran-ether (THF-Et2O); hexane; ethyl acetate;	Preparation 65 1-Chloro-7-sulphamoylisoquinoline n-Butyllithium (0.35 mL, 2.5 M in hexanes, 0.875 mmol) was added dropwise to a stirred solution of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (200 mg, 0.825 mmol) in tetrahydrofuran-ether (THF-Et2O) (2.0 mL, 1: 1) under N2 at -78 3C. After 5 min, the mixture was added to a solution of sulphuryl chloride (SO2Cl2) (0.14 mL, 1.74 mmol) in hexane (2.0 mL) at -25 C. under N2 and the mixture was warmed to 23 C. and stirred for 3 h. Concentrated aqueous ammonia (3.0 mL, 0.880) was added and then all solvents were evaporated in vacuo. The residue was suspended in EtOAc, washed with aqueous HCl (2 M), brine, and then evaporated in vacuo. The residue was purified by column chromatography upon silica gel using hexanes-EtOAc (50:50 to 30:70) as eluant to give the title compound (37 mg, 0.152 mmol) as a white solid. m.p. 220-222 C. 1H (CD3OD, 400 MHz) delta7.9 (1H, d), 8.2 (1H, d), 8.3 (1H, d), 8.4 (1H, d), 8.9 (1H, s) ppm. LRMS 243, 245 (MH+).

Reference： [1]Patent: US6248738,2001,B1

50
[ 292638-84-7 ]
hexanes-EtOAc [ No CAS ]
[ 6163-58-2 ]
[ 215453-51-3 ]
1-Chloro-7-(2-phenyl-E-ethenyl)isoquinoline [ No CAS ]
1-chloro-(2-phenylethen-1-yl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide;	Preparation 43 1-Chloro-7-(2-phenyl-E-ethenyl)isoquinoline A solution of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (200 mg, 0.80 mmol), styrene (94 mg, 0.90 mmol), tri-o-tolylphosphine (30 mg, 12 mol %), palladium (II) acetate (Pd(OAc)2) (10 mg, 5 mol %) and triethylamine (0.34 mL, 2.5 mmol) in DMF (0.75 mL) were placed in a MOS-2000 (650 W) microwave and irradiated at full power for 7*40s (reaction monitored by TLC). The mixture was poured into water and extracted with EtOAc. The combined organic layers were dried over MgSO4, evaporated in vacuo and the residue was purified by column chromatography upon silica gel using hexanes-EtOAc (100:0 to 95:5) as eluant to give 1-chloro-(2-phenylethen-1-yl)isoquinoline (135 mg, 0.508 mmol) as a yellow solid. M.Pt. 118-121 C.; 1H (delta, CDCl3, 300 MHz) 7.3-7.35 (3H, m), 7.44 (2H, dd), 7.55-7.65 (3H, m), 7.8 (1H, d), 8.0 (1H, d), 8.25 (1H, d), 8.3 (1H, s); LRMS 266, 268 (MH); El.Anal. Found: C, 76.87; H, 4.61; N, 5.18. Calcd for C17H12ClN: C, 76.84; H, 4.55; N, 5.27.

Reference： [1]Patent: US6248738,2001,B1

51
[ 215453-51-3 ]
[ 223671-53-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 45 1-chloro-7-isoquinolinecarboxaldehyde The title compound was prepared in a similar manner to Prep.44, from <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong>, as a white solid. 1H (delta, DMSO-d6, 300 MHz) 7.95 (1H, d), 8.2 (2H, s), 8.4 (1H, d), 8.85 (1H, s), 10.2 (1H, s). LRMS 192, 194 (MH).

Reference： [1]Patent: US6248738,2001,B1

52
[ 215453-51-3 ]
7-carboxy-1-chloroisoquinoline hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran;	Preparation 46 7-Carboxy-1-chloroisoquinoline hydrochloride A solution of n-BuLi (1.2 mL, 2.5 M in hexanes, 3.0 mmol) was added dropwise to a stirred solution of the <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (0.64 g, 2.64 mmol) in THF (10 mL) and ether (10 mL) at -78 C. under N2. After 20 min, crushed solid C02 (excess) was added in one portion and the mixture allowed to warm to room temperature. The solvents were evaporated in vacuo and the residue partioned between aqueous NaOH (20 mL, 0.5 M) and ether (50 mL). The aqueous phase was acidified with conc HCl, extracted with EtOAc (3*50 mL) and the combined organic extracts were dried over MgSO4 and evaporated to leave 7-carboxy-1-chloroisoquinoline hydrochloride (0.277 g, 1.13 mmol) as an off-white solid. 1H (delta, DMSO-d6, 300 MHz) 7.95 (1H, d), 8.15 (1H, d), 8.3 (1H, d), 8.4 (1H, d), 8.8 (1H, s), 13.5 (1H, br s); LRMS 208, 210 (MH).

Reference： [1]Patent: US6248738,2001,B1

53
[ 215453-51-3 ]
1-Chloro-7-(1-hydroxy-1-phenylethyl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 49 1-Chloro-7-(1-hydroxy-1-phenylethyl)isoquinoline The title compound was prepared from <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> quenching the formed anion with acetophenone to give a cream solid. M.Pt. 134-5 C.; 1H (delta, CDCl3, 400 MHz) 2.0 (3H, m), 2.3 (1H, br s), 7.2-7.35 (3H, m), 7.35-7.45 (2H, m), 7.5 (1H, d), 7.65 (1H, d), 7.7 (1H, d), 8,2 (1H, d), 8.45 (1H, s); LRMS 284, 286 (MH); El.Anal. found: C, 71.49; H, 5.06; N, 4.90. Calcd for C17H14ClNO+0.08 EtOAc: C, 71.54; H, 5.07; N, 4.82.

Reference： [1]Patent: US6248738,2001,B1

54
[ 215453-51-3 ]
1-Chloro-7-(α-hydroxybenzyl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 50 1-Chloro-7-(alpha-hydroxybenzyl)isoquinoline The title compound was prepared from <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> quenching the formed anion with benzaldehyde to give a white solid. 1H (delta, CDCl3, 300 MHz) 2.45 (1H, d), 6.05 (1H, d), 7.2-7.45 (5H, m), 7.55 (1H, d), 7.7 (1H, d), 7.75 (1H, d), 8.15 (1H, d), 8.4 (1H, s); LRMS 270, 272 (MH); El.Anal. Found: C, 70.1 1; H, 4.63; N, 4.85. Calcd for C16H12ClN+0.2 EtOAc: C, 70.22; H, 4.77; N, 4.87.

Reference： [1]Patent: US6248738,2001,B1

55
hexanes-EtOAc [ No CAS ]
[ 215453-51-3 ]
1-Chloro-7-(1-hydroxycyclohex-1-yl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sec.-butyllithium; In tetrahydrofuran; cyclohexane; water;	Preparation 47 1-Chloro-7-(1-hydroxycyclohex-1-yl)isoquinoline A solution of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (200 mg, 0.82 mmol) in anhydrous THF (4 mL) at -78 C. was treated with s-BuLi (1.3M in cyclohexane, 0.7 mL, 0.91 mmol) to afford a dark green solution which after 4 minutes was quenched with cyclohexanone (100 mL, 0.96 mmol). The cooling bath was removed and the reaction mixture allowed to reach ambient temperature, stirred for 20 minutes and quenched with a drop of water. The THF was removed in vacuo and water (5 mL) added to the residue which was extracted with ethylacetate (3*10 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL) and then dried over MgSO4 and condensed onto silica gel (1 g) and purified by column chromatography (silica gel, 15 g) using hexanes-EtOAc (100:15 to 100:20) as eluant to afford the title compound as a white solid (83 mg, 0.32 mmol). M.Pt. 109.5-111 C.; 1H (delta, CDCl3, 300 MHz) 1.3-2.1 (1H, m), 7.55 (1H, d), 7.85 (1H, d), 7.95 (1H, d), 8.25 (1H, d), 8.45 (1H, s); LRMS 262, 264 (MH).

Reference： [1]Patent: US6248738,2001,B1

56
[ 34551-41-2 ]
[ 215453-51-3 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation 20 7-Bromo-1-chloroisoquinoline The title compound was prepared from a mixture of 5- and 7-bromoisoquinoline N-oxides and separated from 5-bromo-1-chloroisoquinoline by chromatography, to give a white solid. 1H (delta, CDCl3, 300 MHz) 7.5 (1H, d), 7.7 (1H, d), 7.8 (1H, d), 8.3 (1H, d), 8.5 (1H, s); LRMS 244, 246 (MH).

Reference： [1]Patent: US6248738,2001,B1

57
[ 13726-69-7 ]
[ 215453-51-3 ]
[ 1166861-90-0 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 4607 - 4609
[2]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 207 - 212

58
[ 1093124-39-0 ]
[ 215453-51-3 ]
[ 1093124-40-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 7078 - 7081

59
[ 110-85-0 ]
[ 215453-51-3 ]
7-bromo-1-piperazin-1-ylisoquinoline [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 34 - 42

60
[ 57711-45-2 ]
[ 215453-51-3 ]
[ 1170704-53-6 ]
[ 1170704-51-4 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 3277 - 3279

61
[ 13726-69-7 ]
[ 215453-51-3 ]
[ 924271-90-9 ]

Reference： [1]ACS Medicinal Chemistry Letters,2011,vol. 2,p. 207 - 212

62
[ 215453-51-3 ]
[ 1170704-54-7 ]

Yield	Reaction Conditions	Operation in experiment
		Example 63 : N-( l-( (lr,4r)-4-hvdroxy-4-( thiazol-5-yl)cvclohexyl)azetidin-3-yl)-2-ff7- ftrifluoromethyl)iso uinolin-l-yl)amino)acetamideStep A: l-Chloro-7-iodoisoquinoline; To a stirred solution of 7-bromo-l-chloroisoquinoline (15g, 62 mmol) in THF at -78 C, n-BuLi (123.7 mmol) was added. The resulting solution was stirred for 15 min. and, I2 (31.4 mg, 123.7 mmol) in THF was slowly added by syringe over a period of 5 min. The solution was then allowed to reach room temperature and treated with a saturated aqueous Na2S203 solution. The resulting mixture was extracted with diethyl ether (2x). The extracted organic layer was washed with brine, dried over Na2S04 and concentrated in vacuum. The residue was purified by flash chromatography to give the title compound.

Reference： [1]Patent: WO2011/159854,2011,A1 .Location in patent: Page/Page column 132
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

63
[ 215453-51-3 ]
[ 1352934-60-1 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

64
[ 215453-51-3 ]
[ 1196154-02-5 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

65
[ 215453-51-3 ]
[ 1352934-61-2 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

66
[ 215453-51-3 ]
[ 1196147-73-5 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

67
[ 215453-51-3 ]
[ 1352934-62-3 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

68
[ 215453-51-3 ]
[ 1352934-63-4 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

69
[ 215453-51-3 ]
[ 1352934-64-5 ]

Reference： [1]Patent: WO2011/159854,2011,A1
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

70
[ 215453-51-3 ]
benzyl (2-((1-((1r,4r)-4-hydroxy-4-(thiazol-5-yl)cyclohexyl)azetidin-3-yl)amino)-2-oxoethyl)(7-(trifluoromethyl)isoquinolin-1-yl)carbamate [ No CAS ]

Reference： [1]Patent: WO2011/159854,2011,A1

71
[ 215453-51-3 ]
N-(1-((1r,4r)-4-hydroxy-4-(thiazol-5-yl)cyclohexyl)azetidin-3-yl)-2-((7-(trifluoromethyl)isoquinolin-1-yl)amino)acetamide [ No CAS ]

Reference： [1]Patent: WO2011/159854,2011,A1

72
[ 215453-51-3 ]
[ 1374258-31-7 ]

Reference： [1]Patent: US2012/108619,2012,A1

73
[ 124-41-4 ]
[ 215453-51-3 ]
[ 1374258-30-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	In methanol; at 130℃; for 3h;Microwave irradiation; Sealed tube;	<strong>[215453-51-3]7-Bromo-1-chloroisoquinoline</strong> (570 mg, 2.4 mmol) was combined with methanol (10 mL) and sodium methoxide (25 wt % in methanol, 1.5 mL, 24 mmol) in a microwave vial. The vial was sealed and heated to 130 C. for 3 hours in a microwave. The reaction was concentrated. The crude residue was taken up in ethyl acetate and washed with water and saturated aqueous sodium bicarbonate. The aqueous layer was extracted two times with hot ethyl acetate. The combined organics were dried over sodium sulfate, filtered, and concentrated to give the title compound (520 mg, 93%). +ESI (M+H+1) 240.0; 1H NMR (400 MHz, DMSO-d6, delta): 8.25-8.28 (m, 1H), 8.04 (d, J=5.9 Hz, 1H), 7.86-7.89 (m, 2H), 7.40 (dd, J=6.0, 0.9 Hz, 1 H), 4.03 (s, 3H).
	In methanol; at 130℃; for 3h;Sealed tube; Microwave irradiation;	To a suspension of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (0.57 g, 2.3 mmol) in MeOH (8.5 mL) in a 20 mL microwave vial was added sodium methoxide solution (1.5 mL, 24 mmol, 25% weight in MeOH). The resulting reaction mixture was heated at 130C in a sealed vial in a microwave for 3 h. The solvents were removed to give a whitesolid. This solid was partitioned between EtOAc and H20. A saturated solution ofNaHCO3 was added to separate the layers. The aqueous layer was extracted with EtOAc(2x). The combined organic layers were concentrated to give the crude product, 174E(545 mg) which was used without further purification in the next step. MS(ESI) m/z 238.0(M+H)h

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7110 - 7119
[2]Patent: US2012/108619,2012,A1 .Location in patent: Page/Page column 32
[3]Patent: WO2017/40449,2017,A1 .Location in patent: Paragraph 00443

74
[ 215453-51-3 ]
[ 1369280-83-0 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7110 - 7119
[2]Patent: US2012/108619,2012,A1

75
[ 215453-51-3 ]
[ 1374257-78-9 ]

Reference： [1]Patent: US2012/108619,2012,A1

76
[ 144104-59-6 ]
[ 215453-51-3 ]
[ 1332881-28-3 ]

Yield	Reaction Conditions	Operation in experiment
25%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 16h;Inert atmosphere; Reflux;	A mixture of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (0.50 g, 2.1 mmol), 5-indoleboronic acid (0.40 g, 2.5 mmol), tetrakis(triphenylphosphene)palladium (0.035 g, .08 mmol), potassium carbonate (2.1 mL, 2 M, 4.1 mmol), N,N-dimethylformamide (11 mL) was stirred while purging the headspace with argon for 30 min. The mixture was then brought to reflux for 16 h before being allowed to cool to RT. The mixture was filtered through a bed of silica gel, diluted with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated and washed with NaOH (2 x 20 mL, 10 % aq.), water (5 x 30 mL, until refractive changes were no longer seen at the organic-aqueous interface), and ammonium chloride (20 mL, sat.). The organic layer was then adsorbed onto silica gel and flash-chromatographed (ethyl acetate/hexanes) to afford 0.14 g (25 %) of a yellow solid. MS (ESI): calculated for C17HnClN2, 278.1, found 301.0 [M + Na]+. 1H NMR (300 MHz, DMSO-i¾) delta 6.56 - 6.58 (m, 1 H), 7.44 (t, J = 2.77 Hz, 1 H), 7.57 - 7.59 (m, 2 H), 7.93 (m, 1 H), 8.04 (s, 1 H), 8.13 - 8.20 (m, 1 H), 8.27 - 8.31 (m, 2 H), 8.43 (m, 1 H), 11.25 (brs, 1 H).

Reference： [1]Patent: WO2011/109059,2011,A1 .Location in patent: Paragraph 0048; 00398
[2]ACS Medicinal Chemistry Letters,2015,vol. 6,p. 993 - 997

77
[ 144104-59-6 ]
[ 215453-51-3 ]
[ 1332881-29-4 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; for 16h;Inert atmosphere; Reflux;	A mixture of <strong>[215453-51-3]7-bromo-1-chloroisoquinoline</strong> (0.20 g, 2.1 mmol), 5-indoleboronic acid (0.80 g, 5.0 mmol), tetrakis(triphenylphosphene)palladium (0.19 g, 0.16 mmol), potassium carbonate (2.1 mL, 2 M, 4.1 mmol), N,N-dimethylformamide (11 mL) was stirred while purging the headspace with argon for 30 min. The mixture was then brought to reflux for 16 h before being allowed to cool to RT. The mixture was filtered through a bed of silica gel, diluted with water (50 mL), and extracted with ethyl acetate (50 mL). The organic layer was separated and washed with NaOH (2 x 20 mL, 10 % aq.), water (5 x 30 mL, until refractive changes were no longer seen at the organic-aqueous interface), and ammonium chloride (20 mL, sat.). The organic layer was then adsorbed onto silica gel and flash-chromatographed (ethyl acetate/hexanes) to afford 0.29 g (39 ) of a yellow solid. MS (ESI): calculated for C25H17N3, 359.1, found 360.2 [M + H]+ 382.1 [M + Na]+, and 358.0 [M - H]-.1.. NMR (500 MHz, DMSO- d6) delta 6.46 - 6.50 (m, 1 H) 6.52 - 6.59 (m, 1 H) 7.34 - 7.36 (m, 1 H) 7.36 - 7.41 (m, 2 H) 7.42 - 7.52 (m, 3 H) 7.58 (d, 7=8.30 Hz, 1 H) 7.81 (dd, 7=5.49, 5.00 Hz, 2 H) 7.92 (s, 1 H) 8.08 - 8.17 (m, 2 H) 8.33 (s, 1 H) 8.54 (d, 7=5.61 Hz, 1 H) 11.18 (br. s., 1 H) 11.30 (br. s., 1 H) ppm.

Reference： [1]Patent: WO2011/109059,2011,A1 .Location in patent: Paragraph 0048; 00399

78
[ 144104-59-6 ]
[ 215453-51-3 ]
[ 1332881-30-7 ]

Reference： [1]Patent: WO2011/109059,2011,A1

79
[ 215453-51-3 ]
C₃₂H₃₂F₃N₅O₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

80
[ 215453-51-3 ]
C₂₄H₂₆F₃N₅O₂S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1063 - 1069

81
[ 215453-51-3 ]
[ 1374257-08-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7110 - 7119

82
[ 107-31-3 ]
[ 215453-51-3 ]
[ 223671-53-2 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 12509 - 12525
[2]Organic Letters,2014,vol. 16,p. 4972 - 4975

83
[ 215453-51-3 ]
1-(1-chloroisoquinolin-7-yl)but-3-en-1-ol [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4972 - 4975

84
[ 215453-51-3 ]
(E)-methyl 5-(1-chloroisoquinolin-7-yl)-5-hydroxypent-2-enoate [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 4972 - 4975

85
[ 215453-51-3 ]
N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(3-morpholinophenyl)isoquinolin-1-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

86
[ 215453-51-3 ]
N-(4-(benzyloxy)-3-chlorophenyl)-7-(4-(morpholinosulfonyl)-phenyl)isoquinolin-1-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

87
[ 215453-51-3 ]
N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methylpiperazin-1-yl)sulfonyl)phenyl)isoquinolin-1-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

88
[ 215453-51-3 ]
N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)isoquinolin-1-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 5522 - 5537

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
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P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 215453-51-3 ] {[proInfo.proName]}

Quality Control of [ 215453-51-3 ]

Related Doc. of [ 215453-51-3 ]

Product Details of [ 215453-51-3 ]

Calculated chemistry of [ 215453-51-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 215453-51-3 ]

Application In Synthesis of [ 215453-51-3 ]

[ 215453-51-3 ] Synthesis Path-Upstream 1~8

[ 215453-51-3 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 215453-51-3 ]

Bromides

Chlorides

Related Parent Nucleus of [ 215453-51-3 ]

Isoquinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 215453-51-3 ]

Related Parent Nucleus of
[ 215453-51-3 ]