32024-15-0|3-Iodo-4,5-dimethoxybenzaldehyde| Ambeed

CAS No. :	32024-15-0
Formula :	C₉H₉IO₃
M.W :	292.07
SMILES Code :	O=CC1=CC(OC)=C(OC)C(I)=C1
MDL No. :	MFCD00674091
InChI Key :	MVPNBXPAUYYZAF-UHFFFAOYSA-N
Pubchem ID :	2778113

Safety of [ 32024-15-0 ]

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

Computational Chemistry of [ 32024-15-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.22
Num. rotatable bonds	3
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	57.53
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
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	1.98
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.12
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.	1.69
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	2.96
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.17

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.04
Solubility	0.265 mg/ml ; 0.000908 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.	-2.35
Solubility	1.3 mg/ml ; 0.00445 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	-3.54
Solubility	0.0835 mg/ml ; 0.000286 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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.	-6.68 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	2.0 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<0.0
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)	2.05

Application In Synthesis of [ 32024-15-0 ]

* 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.

Downstream synthetic route of [ 32024-15-0 ]

[ 32024-15-0 ] Synthesis Path-Downstream 1~54

1
[ 141-82-2 ]
[ 32024-15-0 ]
(E)-3-iodo-4,5-dimethoxycinnamic acid [ No CAS ]

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 957 - 962.
[2]Ciencia,1955,vol. 15,p. 208.
[3]Journal of Organic Chemistry,1945,vol. 10,p. 527,528,530.
[4]Journal of Organic Chemistry,1945,vol. 10,p. 527,528,530.

2
[ 32024-15-0 ]
[ 5468-22-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20℃; for 4h;Inert atmosphere;	3-Iodo-4,5-dimethoxybenzaldehyde (913 mg, 3.12 mmol) and 2-methyl-2-butene (3.10 mL) were dissolved in tert-butanol (10.0 mL), and a solution of 80% sodium chlorite (564 mg, 6.24 mmol) and monobasic sodium phosphate (487 mg 4.06 mmol) in water (7.00 mL) was added dropwise. The mixture was stirred for 4 h at room temperature. The solvent was removed in vacuo and the residue was diluted with water (40.0 mL). The pH of the solution was adjusted to 10 with 1 M aqueous NaOH, the aqueous phase was extracted with ether (2×20.0 mL). The aqueous layers were acidified to pH 2 by dropwise addition of 3 M aqueous HCl and extracted with ethyl acetate (3×25.0 mL). The combined organic layers were dried over anhydrous MgSO4 and the solvent was removed in vacuo to give a white solid. (Yield: 915 mg, 2.97 mmol, 95%). 1H NMR (d6-DMSO, 400 MHz, 20C): δ = 13.14 (br. s., 1H, COOH), 7.88 (d, J = 2.0 Hz, 1H,ArH), 7.53 (d, J = 1.8 Hz, 1H, ArH), 3.86 (s, 3H, OCH3), 3.77 (s, 3H, OCH3). 13C NMR (d6-DMSO, 100 MHz, 20C): δ = 166.5, 152.9, 152.8, 132.1, 129.3, 114.6, 93.2, 60.9, 56.9. ESMS calcd for C9H8IO4 [M-H]- : 306.9743, found 306.9750
	With sodium chlorite; aminosulfonic acid; In water; acetonitrile; at 20℃; for 0.833333h;	To a stirred solution of <strong>[32024-15-0]3-iodo-4,5-dimethoxybenzaldehyde</strong> (25.0 g, 85.6 mmol) in CH3CN [(800 ML)] at room temperature, was added a solution of sulfamic acid (10.65 g, 109 mmol) in [H20] (135 mL). To this was added, dropwise, a solution of NaClO2 (12.65 g, 112 mmol) in H20 (135 mL) over 20 min period. After stirring for a [FURTHER 30] min at room temperature, the solvent was removed in vacuo. The reaction was diluted [WITLI I.] HCl (700 mL) and extracted with EtOAc (3 x 300 mL). The combined organic layers were washed with brine (600 mL), dried over [NA2S04] and concentrated in vacuo to give 3,4- dimethoxy-5-iodobenzoic acid (26 [G).] The product was used without further purification.

References: [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 117 - 129.
[2]Svensk Kemisk Tidskrift,1935,vol. 47,p. 223,227.
[3]Patent: WO2004/7444,2004,A2 .Location in patent: Page 86-87.

3
[ 32024-15-0 ]
3-iodo-4,5-dimethoxy-benzaldehyde-((<i>E</i>)-oxime ) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With hydroxylamine hydrochloride;	13as) In analogy to Example 13ap), from 3-iodo-4,5-dimethoxy-benzaldehyde and hydroxylamine hydrochloride there is obtained the corresponding 3-iodo-4,5-dimethoxy-benzaldehyde oxime as a colourless solid. Yield: 99%.

References: [1]Patent: US5763450,1998,A .
[2]Proceedings of the Iowa Academy of Science,1938,vol. 45,p. 127,131.

4
[ 5438-36-8 ]
[ 32024-15-0 ]

Yield	Reaction Conditions	Operation in experiment
9.78 g (93%)	With potassium carbonate; In N,N-dimethyl-formamide;	Preparation of 3,4-Dimethoxy-5-iodobenzaldehyde lodomethane (2.5 mL, 40 mmoles) was added to a mixture of 5-iodovanillin (10 g, 36 mmoles), potassium carbonate (25 g, 180 mmoles) in DMF (100 ml) and the resulting mixture was stirred at room temperature for 16 hours. The mixture was poured into water (0.5 L) and extracted with ethyl acetate (2*200 mL). The combined organic phases were washed with water (200 mL), dried over MgSO4 and evaporated in vacuo to afford 9.78 g (93%) of 3,4-dimethoxy-5-iodobenzaldehyde, m.p. 58-63 C.

References: [1]Journal of Organic Chemistry,1943,vol. 8,p. 358,363,365.
[2]Journal of Organic Chemistry,1945,vol. 10,p. 527,528,530.
[3]Journal of Organic Chemistry,1942,vol. 7,p. 354,355.
[4]Patent: US6613942,2003,B1 .
[5]Organic Preparations and Procedures International,2012,vol. 44,p. 146 - 152.

5
[ 5438-36-8 ]
[ 77-78-1 ]
[ 32024-15-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 120℃;	This compound was prepared on a 0.27-mol scale using the method of Nimgirawath [28]. The crude product was recrystallized (4:1 ethanol:water) to give 25.2 g (96%) of 11 as a white solid, mp 71-72 C (lit [28] mp 71-72 C). IR: 2832, 2730, 2693 cm-1; 1H NMR (300 MHz): δ 9.83 (s, 1H), 7.85 (d, 1H, J = 1.7 Hz), 7.41 (d, 1H, J = 1.7 Hz), 3.93 (s, 3H), 3.92 (s, 3H); 13C NMR (75 MHz): δ 189.7, 154.2, 153.0, 134.7, 133.9, 111.0, 92.1, 60.7, 56.1.
96%		5-Iodo-3,4-dimethoxybenzaldehyde (2). A procedure of Nimgirawath’ was modified.A 250-mL, three-necked, round-bottomed flask, equipped with a magnetic stirrer, anaddition funnel and a condenser was charged with 25.0 g (90 mmol) of 1, 100 mL ofDMF and 37.0 g (0.27 mol) of anhydrous K2C03 and stirred for 10 mm. The reactionmixture was placed in a preheated oil bath at 120 C for 15 mm and 34.0 g (0.27 mol) ofdimethyl sulfate added dropwise via a slow portion-wise process over 1 h. The reaction mixture was stirred at 120 C for 18 h and then cooled. The mixture was cautiously added to 400 mL of distilled water and was stirred for 30 mm. The crude product formed was collected and the product was recrystallized from 80:20 ethanol:water to give 25.2 g(96%) of 2 as a white solid, mp 71-72 C (lit’ mp 71-72 C). IR: 2832, 2730, 2693 cm1

References: [1]Australian Journal of Chemistry,1994,vol. 47,p. 957 - 962.
[2]European Journal of Medicinal Chemistry,2012,vol. 54,p. 387 - 396.
[3]ChemMedChem,2012,vol. 7,p. 1974 - 1982.
[4]Patent: WO2013/138787,2013,A1 .Location in patent: Page/Page column 18.
[5]European Journal of Medicinal Chemistry,2020,vol. 200.
[6]Angewandte Chemie - International Edition,2009,vol. 48,p. 4605 - 4609.
[7]Svensk Kemisk Tidskrift,1935,vol. 47,p. 223,227.

6
[ 32024-15-0 ]
[ 4482-29-5 ]
[ 120-14-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 623 - 628.

7
[ 32024-15-0 ]
[ 543-24-8 ]
4-[1-(3-Iodo-4,5-dimethoxy-phenyl)-meth-(Z)-ylidene]-2-methyl-4H-oxazol-5-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2773 - 2780.

8
[ 32024-15-0 ]
[ 2181-42-2 ]
2-(3-Iodo-4,5-dimethoxy-phenyl)-oxirane [ No CAS ]

References: [1]South African Journal of Chemistry,1996,vol. 49,p. 40 - 46.

9
[ 5438-36-8 ]
[ 74-88-4 ]
[ 32024-15-0 ]

Yield	Reaction Conditions	Operation in experiment
98%		General procedure: The methylation reaction of halogenated vanillin derivative (1a-1c) were generally conducted based on the previously reported procedure. 19 In brief, into a solution of halogenated vanillin (1a, 1b, or 1c)(10.17 mmol) in CH2Cl2 (135.0 mL), an aqueous solution of 1.6MNaOH (75.0 mL) and tetrabutylammonium iodide (TBAI) (15.25 mmol)were added. The reaction was stirred until a clear solution was observed. Methyl iodide (120.5 mmol) was added to a solution mixture and stirred for 16 h at room temperature. The reaction was quenchedwith 6M HCl and extracted with CH2Cl2. The organic layer was subsequently washed with H2O followed by saturated NaCl solution. The solution was subsequently dried over Na2SO4 and concentrated todryness, affording crude product as yellow solid. The crude product waspurified by column chromatography to give white solid product 2a-2c.
97%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; at 20℃; for 12h;	General procedure: Following an adaptation of the procedure of McKillop et al.7, anaqueous solution of 1.20 g of NaOH (30 mmol, 3.0 eq.) in 50 mL of deionized water was added to astirring solution of 2.31 g (10 mmol) of 2-bromo-isovanillin (2-bromo-3-hydroxy-4-methoxybenzaldehyde)in 50 mL of dichloromethane. Next, phase transfer catalyst was added, as 3.40 g of eithertetrabutylammonium hydrogen sulfate (TBAHS, 10.0 mmol, 1.0 eq.) or recycled catalyst (assuming thatthe recovered catalyst is tetrabutylammonium hydroxide, 2.6 g is 10 mmol, 1.0 eq). Once dissolved, 17g (120 mmol, 12 eq.) of methyl iodide was then added to the mixture and the reaction was allowed tostir at room temperature. Reaction progress was monitored by HPLC. As monitored by HPLC, reactionprogress generally showed complete turnover to product with no side products by 3 hours, however thesolution was typically allowed to stir overnight for convenience. The reaction mixture was extracted with3 x 50 mL portions of CH2Cl2. The combined organic extracts were washed with brine and deionizedwater, dried over MgSO4, filtered, and concentrated by evaporation under reduced pressure to yield aeither a white or yellow solid. To remove catalyst, the solid was first ground to a fine powder with amortar and pestle. This solid was poured on top of a 2 - 3 cm layer of dry silica gel in a 3 - 4 cm (I.D.)sintered glass fritted Buchner funnel. The solid was extracted with 1:5 ethyl acetate:hexanes in 75 mLportions by pouring the solvent mixture over the dry solids with vacuum suction to collect the solutionin a round bottom flask. Allow the solids to dry between solvent portions for best separation. The first1250 mL typically contained 85 - 95% of pure product. The combined eluent was evaporated to drynessunder reduced pressure to afford a dense, white, flakey solid (2.06 g, 90%). If the product was found tocontain non-halogenated contaminants from the previous step, pure halogenated product was easilyobtained by recrystallization from hexanes. The phase transfer catalyst, presumably a mixture oftetrabutylammonium salts, was recovered by either scooping it out of the filter or by eluting with ethylacetate.
87%		To a solution of 3-iodo-4-hydroxy-5-methoxybenzaldehyde (1.05 g, 3.78 mmol) in CH2Cl2 (50.0 mL) was added aqueous NaOH solution (1.93 g in 30.0 mL of water) and tbutylammonium iodide (2.09 g, 5.66 mmol) and stirred until clear. Methyl iodide (2.80 mL, 45.8 mmol) was added to the reaction mixture and stirred for 12 h at room temperature. The reaction was quenched with 6N HCl, and the organic product was extracted with CH2Cl2, washed with brine, dried, and concentrated to give a solid. The solid was chromatographed (pentane:dichloromethane, 1:1) to give a white solid. (Yield: 957 mg, 3.28 mmol, 87%). 1H NMR (d1-CDCl3, 400 MHz, 20C): δ = 9.81 (s, 1H, C(O)H), 7.83 (d, J = 1.8 Hz, 1H, ArH), 7.39 (d, J = 1.8 Hz, 1H, ArH), 3.91 (m, 6H, 2x OCH3). 13C NMR (d1-CDCl3, 100 MHz, 20C): δ = 189.7, 154.1, 153.0, 134.6, 133.9, 111.1, 92.1, 60.6, 56.1. ESMS calcd for C9H10IO3 [M+H]+ : 292.9669, found 292.9675.

57%		Preparation of 7-ethoxy-4-(3-iodo-4,5-dimethoxybenzyl)isoquinolin-8-ol hydrochloride 723-lodo-4,5-dimethoxybenzaldehvde RBO 40110In a 100 mL round bottom flask 3-iodo-4-hydroxy-5-methoxybenzaldehyde (1 .0 g, 3.60 mmol) was dissolved in acetone (50 mL) and K2CO3 (746 mg, 5.40 mmol) was added at RT. The reaction mixture was stirred at RT for 30 min, then iodomethane (766 mg, 5.40 mmol) was added and reaction was stirred at reflux for another 4 h. Acetone was removed and the residue was taken back in EtOAc (50 mL) and H2O (50 ml_). The aqueous layer was further extracted with EtOAc (3x50 ml_). The combined rganics layers were washed with brine (50 ml_), dried over Na2SO4, filtered and concentrated to dryness to give 3-iodo-4,5-dimethoxybenzaldehyde RBO 40110 (603 mg, 57% yield) as a brown oil.RBO 40110MW: 292.07; Yield: 57%; Brown oil.1H-NMR (CDCIs, δ): 3.93 (s, 6H, 2xOMe), 7.41 (s, 1 H, ArH), 7.84 (s, 1 H, ArH), 9.82 (s, 1 H, CHO).MS-ESI m/z (% rel. Int.): 293 ([MH]+, 100).HPLC: Method A, XBridge column, detection UV 254 nm, RT = 5.53 min, peak area 97.0%.
	With potassium carbonate; In N,N-dimethyl-formamide;	3,4-Dimethoxy-5-iodo-benzaldehyde (compound 102, FIG. 1) A mixture of 5-iodovanillin (7 g, 25.18 mmole), potassium carbonate (8.78 g, 63.53 mmole) and iodomethane (6.43 g, 45.30 mmole) was suspended in 60 mL of DMF and stirred at room temperature for 14 hours. The reaction mixture was quenched with water and extracted with diethyl ether. The organic layer was dried over MgSO4, filtered and evaporated in vacuo to obtain a solid which was recrystallized from hexane/ethyl acetate (2:1) (6.28 g, 85.4%).

References: [1]South African Journal of Chemistry,1996,vol. 49,p. 40 - 46.
[2]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 5343 - 5348.
[3]Synthetic Communications,2009,vol. 39,p. 506 - 515.
[4]Synlett,2014,vol. 25,p. 2891 - 2894.
[5]European Journal of Medicinal Chemistry,2017,vol. 125,p. 117 - 129.
[6]Patent: WO2011/151423,2011,A1 .Location in patent: Page/Page column 181-182.
[7]Patent: US5358938,1994,A .

10
[ 201230-82-2 ]
[ 32024-15-0 ]
4-Bu₃Sn,2Cl-C₆H₃CONH-Rink resin [ No CAS ]
2-chloro-4-(5-formyl-2,3-dimethoxy-benzoyl)-benzamide [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 175 - 177.

11
[ 32024-15-0 ]
[ 10365-98-7 ]
4,5-dimethoxy-[3-(3-methoxyphenyl)]benzaldehyde [ No CAS ]

References: [1]Organic Letters,2001,vol. 3,p. 2149 - 2151.

12
[ 32024-15-0 ]
[ 106-95-6 ]
[ 67483-49-2 ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 1017 - 1021.
[2]Synthesis,2005,p. 2625 - 2629.

13
[ 32024-15-0 ]
[ 109-77-3 ]
[ 99-07-0 ]
2-Amino-3-cyano-7-dimethylamino-4-(3-iodo-4,5-dimethoxyphenyl)-4H-chromene [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 6299 - 6310.

14
[ 32024-15-0 ]
[ 1530-32-1 ]
[ 7306-46-9 ]
5-[(Z)-3-(3,4-Dimethoxy-phenyl)-2-methyl-propenyl]-1-iodo-2,3-dimethoxy-benzene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 2446 - 2449.

15
[ 32024-15-0 ]
[ 126-30-7 ]
2-(3-iodo-4,5-dimethoxyphenyl)-5,5-dimethyl-1,3-dioxane [ No CAS ]

References: [1]Journal of Organic Chemistry,2001,vol. 66,p. 8127 - 8134.

16
[ 59649-56-8 ]
[ 32024-15-0 ]
[ 109-77-3 ]
2,7,8-triamino-4-(3-iodo-4,5-dimethoxy-phenyl)-4<i>H</i>-chromene-3-carbonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 4745 - 4751.

17
[ 7677-24-9 ]
[ 32024-15-0 ]
(3-iodo-4,5-dimethoxyphenyl)trimethylsilanyloxyacetonitrile [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 617 - 619.

18
[ 589-87-7 ]
[ 32024-15-0 ]
4'-bromo-5,6-dimethoxy-biphenyl-3-carbaldehyde [ No CAS ]

References: [1]Synthesis,2005,p. 2625 - 2629.

19
[ 32024-15-0 ]
[ 51934-41-9 ]
ethyl 5'-formyl-2',3'-dimethoxybiphenyl-4-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 6040 - 6044.

20
[ 911047-47-7 ]
[ 32024-15-0 ]
3-(3-iodo-4,5-dimethoxyphenyl)-2-(3,4-dimethoxyphenyl)acrylic acid ethyl ester [ No CAS ]

References: [1]Synthesis,2006,p. 2103 - 2112.

21
[ 32024-15-0 ]
[ 109-77-3 ]
[ 2439-04-5 ]
C₂₁H₁₆IN₃O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2858 - 2864.

22
[ 90-15-3 ]
[ 32024-15-0 ]
[ 109-77-3 ]
C₂₂H₁₇IN₂O₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2858 - 2864.

23
[ 32024-15-0 ]
3-(furan-2-carbonyl)-4,5-dimethoxybenzaldehyde [ No CAS ]

References: [1]Organic Letters,2006,vol. 8,p. 617 - 619.

24
[ 32024-15-0 ]
[ 726193-21-1 ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 2446 - 2449.

25
[ 32024-15-0 ]
11H-2-iodo-9,10-dihydro-10-methyl-3,4,6,7-tetramethoxydibenzo[a,c]cycloheptene [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2004,vol. 43,p. 2446 - 2449.

26
[ 32024-15-0 ]
6-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenyl]-hex-5-ynoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1811 - 1815.

27
[ 32024-15-0 ]
4-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-benzoic acid [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1811 - 1815.

28
[ 32024-15-0 ]
6-methyl-1-[(3-iodo-4,5-dimethoxy-phenyl)-methyl]-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2773 - 2780.

29
[ 32024-15-0 ]
[ 18111-03-0 ]