[ CAS No. 885518-49-0 ] {[proInfo.proName]}

Name: 885518-49-0|Methyl 6-bromo-1H-indazole-4-carboxylate|97%
Brand: Ambeed
SKU: A164565
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Quality Control of [ 885518-49-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 885518-49-0 ]

SDS Specification

Alternatived Products of [ 885518-49-0 ]

Product Details of [ 885518-49-0 ]

CAS No. :	885518-49-0	MDL No. :	MFCD07781319
Formula :	C₉H₇BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FEPRHRPOKPTRQZ-UHFFFAOYSA-N
M.W :	255.07	Pubchem ID :	24728062
Synonyms :

Calculated chemistry of [ 885518-49-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	55.07
TPSA :	54.98 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) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.62
Log Po/w (XLOGP3) :	2.1
Log Po/w (WLOGP) :	2.11
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	2.51
Consensus Log Po/w :	2.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.09
Solubility :	0.208 mg/ml ; 0.000816 mol/l
Class :	Soluble
Log S (Ali) :	-2.88
Solubility :	0.332 mg/ml ; 0.0013 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.84
Solubility :	0.0365 mg/ml ; 0.000143 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.82

Safety of [ 885518-49-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 885518-49-0 ]

* 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 [ 885518-49-0 ]
Downstream synthetic route of [ 885518-49-0 ]

[ 885518-49-0 ] Synthesis Path-Upstream 1~8

1
[ 1346597-55-4 ]
[ 885518-49-0 ]

Yield	Reaction Conditions	Operation in experiment
71.7%	Stage #1: With hydrogenchloride In methanol; water at 60℃; for 8 h; Stage #2: With sodium hydrogencarbonate In methanol; water	[01044] Step 6: methyl 6-bromo-lH-indazole-4-carboxylate[01045] To a stirred solution of methyl l-acetyl-6-bromo-lH-indazole-4-carboxylate (18 g, 61.0 mmol) in methanol (350 mL), 6N HC1 (350 mL) was added and stirred it at 60 °C for 8 h. On completion of reaction, solvent was removed under reduced pressure then basified with saturated NaHC0₃ solution till pH 8. The solid precipitate was filtered and dried under vacuum before being stirred in diethyl ether for 15 min, filtered and dried to afford methyl 6-bromo-lH-indazole-4-carboxylate (11 g, 71 .7percent).

Reference： [1] Patent: WO2012/118812, 2012, A2, . Location in patent: Page/Page column 313
[2] Patent: CN105037360, 2016, B, . Location in patent: Paragraph 0400; 0401; 0402

2
[ 67-56-1 ]
[ 885523-08-0 ]
[ 885518-49-0 ]

Yield	Reaction Conditions	Operation in experiment
2.54 g	With hydrogenchloride In water at 70℃; for 18 h;	Methyl 6-bromo-1H-indazole-4-carboxylate Concentrated hydrochloric acid (46.9 ml, 1543 mmol) was added to a stirred suspension of 6-bromo-1H-indazole-4-carboxylic acid (4.65 g, 19.29 mmol, available from Sinova) in methanol (100 ml) and the reaction mixture was heated to 70° C. for 18 h. The reaction mixture was allowed to cool to RT resulting in the precipitation of a solid. The mixture was cooled in ice and the yellow precipitate filtered off and washed with methanol to give the title compound as a yellow solid (2.54 g). LCMS (Method A): Rt=0.90 mins, MH+ 255/257.

Reference： [1] Patent: WO2010/102958, 2010, A1, . Location in patent: Page/Page column 120
[2] Patent: US9326987, 2016, B2, . Location in patent: Page/Page column 118

3
[ 107650-20-4 ]
[ 885518-49-0 ]

Reference： [1] Patent: WO2012/118812, 2012, A2,
[2] Patent: CN105037360, 2016, B,

4
[ 220514-28-3 ]
[ 885518-49-0 ]

Reference： [1] Patent: WO2012/118812, 2012, A2,
[2] Patent: CN105037360, 2016, B,

5
[ 1975-50-4 ]
[ 885518-49-0 ]

Reference： [1] Patent: WO2012/118812, 2012, A2,
[2] Patent: CN105037360, 2016, B,

6
[ 1000342-11-9 ]
[ 885518-49-0 ]

Reference： [1] Patent: WO2012/118812, 2012, A2,
[2] Patent: CN105037360, 2016, B,

7
[ 885518-49-0 ]
[ 1346702-54-2 ]

Reference： [1] Patent: WO2011/140325, 2011, A1,
[2] Patent: WO2012/118812, 2012, A2,
[3] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 12, p. 1091 - 1096

8
[ 885518-49-0 ]
[ 1346704-33-3 ]

Reference： [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 12, p. 1091 - 1096

[ 885518-49-0 ] Synthesis Path-Downstream 1~88

1
[ 352-34-1 ]
[ 885518-49-0 ]
[ 1194020-00-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;trans-N,N'-dimethyl-1,2-cyclohexyldiamine; In N,N-dimethyl-formamide; at 20 - 120℃;Inert atmosphere; sealed tube;	A mixture of <strong>[885518-49-0]6-bromo-4-indazolecarboxylic acid methyl ester</strong> (2.0 g, 7.8 mmol), copper(I) iodide (0.4 g, 0.2 mmol), potassium carbonate (1.2 g, 8.5 mmol) and 4- fluoroiodobenzene (1.8 g, 8.5 mmol) was charged in a sealed tube at room temperature. The tube was evacuated and back-filled with argon, and DMF (10 mL) and x&c-trans- N,N'-dimethylcyclohexane-l,2-diamine (0.20 g, 1.4 mmol) was added. The solution was stirred at 120 0C for 3 hours, cooled to room temperature, and diluted with water (30 mL) and ethyl acetate (50 mL). The organic layer was separated, washed with brine (10 mL) and dried over sodium sulfate. The solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes to afford 6-bromo-l-(4-fluoro-phenyl)-lH-indazole-4-carboxylic acid methyl ester.

Reference： [1]Patent: WO2009/134666,2009,A1 .Location in patent: Page/Page column 74-75

2
[ 885518-49-0 ]
[ 536-74-3 ]
[ 1244017-28-4 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutyl ammonium fluoride;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 80℃; for 2h;Inert atmosphere; sealed tube;	Example 58; JV-Hydroxy-6-(phenylethynyl)- 1 H-indazole-4-carboxamide; Methyl 6-bromo-lH-indazole-4-carboxylate (0.20 g, 0.87 mmol) was dissolved in1.5 niL IN TBAF in THF to which 0.40 mL of ethynylbenzene was added. This was followed by 4 mg of bis(triphenylphosphine)palladium(II) dichloride. The reaction vessel was sealed and evacuated followed by filling with N2 (repeated three times). The reaction was then heated at 80 0C for 2 hours. The reaction was then cooled to room temperature. LCMS analysis indicated conversion to the desired product. The crude mixture was then concentrated in vacuo and purified by preparatory HPLC (Gilson) in a 0-90% MeCN/Water (with 0.1 % TFA ) gradient over 15 minutes. 0.22 g of 90% (purity by LCMS UV) methyl 6-(phenylethynyl)-lH-indazole-4-carboxylate was isolated. The isolated product was then stirred overnight in 1 mL MeOH containing 50% aqueous hydroxylamine. The reaction was concentrated in vacuo. The resulting residue was dissolved in 1 mL DMF and purified by preparatory HPLC (Gilson) in a 0-90% MeCN/Water (with 0.1 % TFA ) gradient over 15 minutes. 7.5 mg of JV-hydroxy-6- (phenylethynyl)-l H-indazole-4-carboxamide was isolated (97.2 % purity by LCMS UV).JV-hydroxy-6-(phenylethynyl)- 1 H-indazole-4-carboxamide : LC-MS : [M+H] 277.96 Mass Calculated for Ci6HnN3O2, 277.281H NMR (300 MHz, CD3OD) delta: ppm 8.4 (s, IH), 7.9 (s, IH), 7.5-7.65 (m, 3H), 7.42 (bs,3H).Methyl 6-(phenylethynyl)-lH-indazole-4-carboxylate: LC-MS : [M+H] 276.99 Mass Calculated for Ci7Hi2N2O2, 276.291H NMR (300 MHz, DCD3OD) delta: ppm 8.5 (s, IH), 8.0 (d, 2H), 7.54 (m, 2H),7.42 (d, 3H), 4.07 (s, 3H).

Reference： [1]Patent: WO2010/100475,2010,A1 .Location in patent: Page/Page column 134-135

3
[ 885518-49-0 ]
[ 98-59-9 ]
[ 1245465-61-5 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (1.289 g, 32.2 mmol) was added portion wise to a solution of methyl 6- bromo-1 H-indazole-4-carboxylate (4.11 g, 16.11 mmol) in N,N-dimethylformamide (50 ml) at O0C. The dark orange mixture was stirred at O0C for 10 mins, then treated with 4- methylbenzenesulfonyl chloride (3.38 g, 17.72 mmol). The resultant pale cream mixture was stirred for 30 mins at O0C then poured into water (1000 ml). The cream precipitate was filtered off under vacuum and dried in the vacuum oven at 5O0C for 18 h to give the title compound as a yellow solid (5.51g). LCMS (Method B): Rt 3.57 mins, MH+ 409/ 411.
5.51 g		Methyl 6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indazole-4-carboxylate Sodium hydride (1.289 g, 32.2 mmol) was added portion wise to a solution of <strong>[885518-49-0]methyl 6-bromo-1H-indazole-4-carboxylate</strong> (4.11 g, 16.11 mmol) in N,N-dimethylformamide (50 ml) at 0 C. The dark orange mixture was stirred at 0 C. for 10 mins, then treated with 4-methylbenzenesulfonyl chloride (3.38 g, 17.72 mmol). The resultant pale cream mixture was stirred for 30 mins at 0 C. then poured into water (1000 ml). The cream precipitate was filtered off under vacuum and dried in the vacuum oven at 50 C. for 18 h to give the title compound as a yellow solid (5.51 g). LCMS (Method B): Rt 3.57 mins, MH+ 409/411.

Reference： [1]Patent: WO2010/102958,2010,A1 .Location in patent: Page/Page column 121
[2]Patent: US9326987,2016,B2 .Location in patent: Page/Page column 118

4
[ 67-56-1 ]
[ 885523-08-0 ]
[ 885518-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; at 70℃; for 18h;	Concentrated hydrochloric acid (46.9 ml, 1543 mmol) was added to a stirred suspension of 6-bromo-1 H-indazole-4-carboxylic acid (4.65g, 19.29 mmol, available from Sinova) in methanol (100 ml) and the reaction mixture was heated to 7O0C for 18 h. The reaction mixture was allowed to cool to RT resulting in the precipitation of a solid. The mixture was cooled in ice and the yellow precipitate filtered off and washed with methanol to give the title compound as a yellow solid (2.54 g). LCMS (Method A): Rt = 0.90mins, MH+ 255/257.
2.54 g	With hydrogenchloride; In water; at 70℃; for 18h;	Methyl 6-bromo-1H-indazole-4-carboxylate Concentrated hydrochloric acid (46.9 ml, 1543 mmol) was added to a stirred suspension of 6-bromo-1H-indazole-4-carboxylic acid (4.65 g, 19.29 mmol, available from Sinova) in methanol (100 ml) and the reaction mixture was heated to 70 C. for 18 h. The reaction mixture was allowed to cool to RT resulting in the precipitation of a solid. The mixture was cooled in ice and the yellow precipitate filtered off and washed with methanol to give the title compound as a yellow solid (2.54 g). LCMS (Method A): Rt=0.90 mins, MH+ 255/257.

Reference： [1]Patent: WO2010/102958,2010,A1 .Location in patent: Page/Page column 120
[2]Patent: US9326987,2016,B2 .Location in patent: Page/Page column 118

5
[ 885518-49-0 ]
[ 1245465-67-1 ]

Yield	Reaction Conditions	Operation in experiment
		Sodium hydride (0.690 g, 17.25 mmol) was added to a 250ml round bottom flask and tetrahydrofuran (THF) (6OmL) was added. The mixture was stirred for 10 minutes in an ice bath then methyl 6-bromo-1 H-indazole-4-carboxylate (4 g, 15.68 mmol) was added portionwise and stirred until no further effervescence was seen (10 minutes). lodomethane (5 ml_, 80 mmol) was then added to the flask and the mixture stirred at 00C for 1 hour, then the ice bath was removed and a water bath at room temperature used and the reaction left overnight (30 hours). The solvent was removed in vacuo to give a yellow cream. The crude was partitioned between water (2OmL) and DCM (2OmL) then the solvent was removed in vacuo to give a yellow solid (2.2g) This was purified by chromatography on silica using a 5Og Si cartridge and run on Flash Master Il using a gradient of 0-100% EtOAc/cyclohexane over 30min. The resultant fractions were analysed by HPLC and fractions containing the two regioisomers were independently combined and the solvent removed in vacuo. The title compound methyl 6-bromo-1 -methyl-1 H-indazole- 4-carboxylate was isolated as white solid (730 mg). LCMS (Method A): R11.03 min, MH+ 270. Regiochemistry confirmed by NMR.Methyl 6-bromo-2-methyl-1 H-indazole-4-carboxylate was also isolated as white solid (750 mg).LCMS (Method A): Rt 0.97 min, MH+ 270. Regiochemistry confirmed by NMR.

Reference： [1]Patent: WO2010/102958,2010,A1 .Location in patent: Page/Page column 124; 125

6
[ 74-96-4 ]
[ 885518-49-0 ]
[ 1346703-15-8 ]
[ 1346703-16-9 ]

Yield	Reaction Conditions	Operation in experiment
25%; 18%	With potassium carbonate; In N,N-dimethyl-formamide; at 20 - 50℃; for 2h;	a) 6-bromo-l-ethyl-lH-indazole-4-carboxylic acid methyl ester and methyl 6-bromo-2-ethyl-2 - indazole-4-carboxylateTo a stirred suspension of 6-bromo-lH-indazole-4-carboxylic acid methyl ester (2.5 g, 9.8 mmol) and K2C03 (2 g,14.7 mmol) in DMF (50 mL) was added 1 -bromo ethane (1.28 g,l 1.76 mmol) at RT. The contents were stirred for 2 h at 50 C. The reaction mixture was then diluted with water (100 mL) and extracted with ethyl acetate (3x50 mL). The combined organic layers were washed with water (3x30 mL), brine solution (2x30 mL), dried over anhydrous sodium sulphate, and filtered. The crude product was purified by silica gel chromatography (eluent: 0 to 30% EtOAc in petroleum ether) to afford the title compound 6-bromo-l-ethyl-lH-indazole-4-carboxylic acid methyl ester (700 mg, 25%) and the undesired isomer 6-bromo-2-ethyl-2H-indazole-4-carboxylic acid methyl ester (500 mg, 18%) as white solids. ¾ NMR (400 MHz, DMSO-d6) (1 -ethyl isomer) : delta 1.41-1.37 (t, 3H), 3.95 (s, 3H), 4.51-4.49 (m, 2H), 7.85-7.84 (d, J = 1.2 Hz, 1H), 8.41-8.39 (d, J = 10 Hz, 1H). LCMS (ES+): m/z=283 [M+l], 285.02 [M+2].

Reference： [1]Patent: WO2011/140325,2011,A1 .Location in patent: Page/Page column 72

7
[ 885518-49-0 ]
[ 75-26-3 ]
[ 1346702-53-1 ]
[ 1346702-52-0 ]

Yield	Reaction Conditions	Operation in experiment
43%; 40%		a) Methyl 6-bromo-l-(l-methylethyl)-l//-indazole-4-carboxylateTo a cooled (0 C) solution of methyl 6-bromo- lH-indazole-4-carboxylate (1.25g, 4.90 mmol) in N,N-dimethylformamide (25 mL) was added sodium hydride (0.216 g, 5.39 mmol). The reaction mixture was stirred for 15 min, then 2-bromopropane (0.920 mL, 9.80 mmol) was added and the reaction allowed to warm to RT. The reaction was maintained at RT overnight. The contents were concentrated to about 1/2 volume, then poured into saturated NH4C1 (200 mL) with stirring. The contents were extracted with ether (2x) and the combined organics washed with brine, dried (MgS04), filtered, and concentrated to give an orange residue (1.55 g crude). Purification by silica gel chromatography (eluent : 5-25% ethyl acetate in hexanes) gave methyl 6-bromo-l-(l-methylethyl)- lH-indazole-4-carboxylate (0.60 g, 40 % yield) and methyl 6-bromo-2-(l-methylethyl)-2H-indazole- 4-carboxylate (0.65 g, 43 % yield). Both products were isolated and methyl 6-bromo-l-(l- methylethyl)-lH-indazole-4-carboxylate was taken on to the next step. Data for 1 -alkylated isomer : .H NMR (400 MHz, CHLOROFORM- d) delta ppm 8.48 (s, 1 H) 8.02 (d, J=1.52 Hz, 1 H) 7.85 (s, 1 H) 4.83 (dt, J=13.33, 6.60 Hz, 1 H) 4.04 (s, 3 H) 1.63 (s, 3 H) 1.61 (s, 3 H); LC-MS(ES) [M+H]+ 297.5/299.5. Data for 2-alkylated isomer : .H NMR (400 MHz, DMSO-J6) delta ppm 8.72 (s, 1 H), 8.25 (s, 1 H), 7.80 (d, J=1.5 Hz, 1 H), 4.96 (m, 1 H), 3.95 (s, 3 H), 1.57 (d, J=6.6 Hz, 6 H); LC-MS(ES) [M+H]+ 297.5/299.5.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 7617 - 7633
[2]Patent: WO2011/140325,2011,A1 .Location in patent: Page/Page column 40
[3]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1091 - 1096
[4]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 334 - 340

8
[ 1556-18-9 ]
[ 885518-49-0 ]
[ 1346703-23-8 ]

Yield	Reaction Conditions	Operation in experiment
32%		a) methyl 6-bromo-l-cyclopentyl-lH-indazole-4-carboxylateIce-cooled methyl 6-bromo-lH-indazole-4-carboxylate (2 g, 7.84 mmol) in 30 mL of DMF was treated with NaH (60%, 345 mg, 8.63 mmol) and the mixture was stirred for 1 hr at 0 C. Iodocyclopentane (2.31 g, 1 1.8 mmol) was then added and the mixture was stirred at 100 C overnight. After cooling to RT, the reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed with water and brine, dried over MgSO^, filtered and evaporated. Hexanes was added to the brown oil and it was purified using silica gel chromatography (eluent: Hex/EtOAc , gradient 0 to 25%). The less polar product was evaporated to give an orange oil, and was dried on hivac overnight. The product was confirmed to be the alkylated 1 -isomer as suggested by 2D HNMR, and was collected as 807 mg (32%). .H NMR (400 MHz, DMSO-d6): delta 8.40 (s, 1 H) 8.37 (s, 1 H) 7.81 (d, J=1.52 Hz, 1 H) 5.26 (quin, J=7.07 Hz, 1 H) 3.95 (s, 3 H) 2.08 - 2.17 (m, 2 H) 1.93 - 2.01 (m, 2 H) 1.82 - 1.92 (m, 2 H) 1.64 - 1.73 (m, 2 H); LCMS (ES+): m/z= 323.3/325.3

Reference： [1]Patent: WO2011/140325,2011,A1 .Location in patent: Page/Page column 75

9
[ 885518-49-0 ]
[ 411235-57-9 ]
[ 1346703-50-1 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium carbonate;[2,2]bipyridinyl; copper diacetate; In 1,2-dichloro-ethane; at 70℃;	a) Methyl 6-bromo-l-cyclopropyl-l/ -indazole-4-carboxylateMethyl 6-bromo-lH-indazole-4-carboxylate (1.0 g, 3.92 mmol) was dissolved in 1 ,2-Dichloroethane (DCE) (14 mL) and stirred for 15 min. Next added cyclopropylboronic acid (0.674 g, 7.84 mmol) and sodium carbonate (0.831 g, 7.84 mmol). The reaction was stirred at RT (suspension). Copper (II) acetate (0.712 g, 3.92 mmol) and 2,2'-bipyridine (0.612 g, 3.92 mmol) were suspended in DCE (24 mL) with heating and the hot suspension was added to the reaction mixture. The contents were stirred with heating at 70 C overnight. After cooling to RT, the reaction mixture was poured onto sat. NH4CI and ice. Next added DCM and stirred for 10 min. The contents were filtered through Celite, washing with water and DCM. The layers were separated and the aq. layer was extracted with DCM (lx). The combined organic layers were washed with brine, dried over MgS04, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography (3-25% gradient ethyl acetate in hexanes) wherein the less polar product was observed to be the title compound, and was collected as a yellow solid (0.54g, 46%); H NMR (400 MHz, DMSO-d6) delta ppm 1.10 - 1.20 (m, 4 H), 3.81 - 3.90 (m, 1 H), 3.95 (s, 3 H), 7.86 (d, J=1.52 Hz, 1 H), 8.30 (d, J=1.77 Hz, 1 H), 8.32 (d, J=1.01 Hz, 1 H); LC-MS (ES) m/z = 295.1 [M+H]

Reference： [1]Patent: WO2011/140325,2011,A1 .Location in patent: Page/Page column 90-91

10
[ 885518-49-0 ]
[ 1346702-51-9 ]

Reference： [1]Patent: WO2011/140325,2011,A1
[2]Patent: WO2012/118812,2012,A2
[3]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1091 - 1096

11
[ 885518-49-0 ]
[ 1346702-55-3 ]