[ CAS No. 52898-49-4 ] {[proInfo.proName]}

Name: 52898-49-4|N,4-Dimethoxy-N-methylbenzamide|95%
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Quality Control of [ 52898-49-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 52898-49-4 ]

Product Details of [ 52898-49-4 ]

CAS No. :	52898-49-4	MDL No. :	MFCD02684314
Formula :	C₁₀H₁₃NO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FIRHLPVYIMMZPV-UHFFFAOYSA-N
M.W :	195.22	Pubchem ID :	15105748
Synonyms :

Calculated chemistry of [ 52898-49-4 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.92
TPSA :	38.77 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) :	-6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.23
Log Po/w (XLOGP3) :	1.01
Log Po/w (WLOGP) :	1.33
Log Po/w (MLOGP) :	1.5
Log Po/w (SILICOS-IT) :	0.84
Consensus Log Po/w :	1.38

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.74
Solubility :	3.55 mg/ml ; 0.0182 mol/l
Class :	Very soluble
Log S (Ali) :	-1.41
Solubility :	7.53 mg/ml ; 0.0386 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.33
Solubility :	0.915 mg/ml ; 0.00469 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 52898-49-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 52898-49-4 ]

* 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.

Downstream synthetic route of [ 52898-49-4 ]

[ 52898-49-4 ] Synthesis Path-Downstream 1~88

1
[ 2614-48-4 ]
[ 6214-19-3 ]
[ 52898-49-4 ]

Reference： [1]Canadian Journal of Chemistry,1991,vol. 69,p. 798 - 810
[2]Canadian Journal of Chemistry,1991,vol. 69,p. 798 - 810

2
[ 52898-49-4 ]
[ 155826-81-6 ]
[ 155826-83-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 459 - 464
[2]Tetrahedron Letters,1994,vol. 35,p. 2919 - 2920

3
[ 52898-49-4 ]
[ 37610-80-3 ]
[ 147030-66-8 ]

Reference： [1]Chimia,1995,vol. 49,p. 381 - 385

4
[ 100-09-4 ]
[ 1117-97-1 ]
[ 52898-49-4 ]

Yield	Reaction Conditions	Operation in experiment
98%		General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether-EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97%).
89%	With Bromotrichloromethane; 4-(diphenylphosphino)-benzyltrimethylammonium bromide; triethylamine; In tetrahydrofuran; at 60℃; for 6h;Inert atmosphere;	General procedure: IS-PPh3 (746 mg, 1.8 mmol) was dried by a vacuum pump for 2 h at 70 C. To a flask containing IS-PPh3 were added 4-methoxycarboxylic acid (152 mg, 1.0 mmol), BrCCl3 (357 mg, 1.8 mmol), benzylamine (129 mg, 1.2 mmol), triethylamine (0.14 mL, 1.0 mmol), and THF (4 mL). The obtained mixture was stirred for 6 h at 60 C under Ar atmosphere. After the reaction, diethyl ether (10 mL) and aq HCl (1 M, 2 mL) were added at 0 C and the obtained mixture was stirred for 15-30 min at room temperature. Then, the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with diethyl ether (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzyl-4-methoxybenzamide was obtained in 93% yield with 99% purity, as estimated by 1H NMR measurement. For cinnamic and aliphatic amides (entries 18-25 in Table 2) and indole-2-carboxamide (entry 16 in Table 2), the reaction mixture was poured into water (8 mL) and the obtained mixture was extracted with chloroform (10 mL×4). The combined organic layer was washed with water (10 mL) and brine (10 mL), and then dried over Na2SO4. After removal of the solvent under reduced pressure, N-benzylamide was obtained. or the recovery of IS-Ph3PO, NaCl (5.0 g) was added to the aqueous layer. The aqueous solution was extracted with CHCl3 (10 mL×5) and the combined organic layer was dried over NaSO4. After removal of the solvent, IS-Ph3PO containing a trace amount of IS-Ph3P was obtained in 95% yield.

Reference： [1]Synthesis,2014,vol. 46,p. 320 - 330
[2]Tetrahedron,2013,vol. 69,p. 3971 - 3977
[3]Chimia,1995,vol. 49,p. 381 - 385

5
[ 53875-17-5 ]
[ 33613-52-4 ]
[ 100-68-5 ]
[ 52898-49-4 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 2738 - 2741

6
[ 70744-47-7 ]
[ 30289-28-2 ]
[ 52898-49-4 ]

Reference： [1]Chemistry Letters,1998,p. 163 - 164

7
[ 52898-49-4 ]
[ 508191-77-3 ]
C₁₆H₁₂N₂O₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 1509 - 1512

8
[ 100-07-2 ]
[ 1117-97-1 ]
[ 52898-49-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 2h;Inert atmosphere;	General procedure: To a stirred solution of acid (1 equiv) in CH2Cl2 (for a solution of0.1 mol L1) were added oxalyl chloride [(COCl)2; 1.25 equiv] and DMF (0.004 equiv) at room temperature. After 1.5 h, the solventand the excess oxalyl chloride were removed by evaporation under vacuum. CH2Cl2 (for a solution of 0.1 mol L1), N,O-dimethylhydroxylamine (1.4 equiv), and Et3N (3 equiv) were then successively added at room temperature. After 2 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with CH2Cl2. The combined organic layers were then washed with a saturated solution of NH4Cl and brine. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude Weinreb amine.To a stirred solution of diisopropylamine (DIPA; 3 equiv) in THF (for a solution of 0.1 mol L1) was added n-Butyl lithium (nBuLi,1.2 M in hexane, 3.1 equiv) at -78 C. After 30 min at 0 C, the medium was recooled to -78 C and freshly distilled tBu acetate (3 equiv) was added. After 30 min at -78 C, crude Weinreb amide (1 equiv) was added at this temperature. After 1 h, the reaction was quenched at room temperature with a saturated solution of NaHCO3 and the mixture extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was then dried with anhydrous MgSO4, filtered, and concentrated under vacuum to afford the crude tert-butyl ester. To a stirred solution of tert-butyl ester (1 equiv) in acetone (10 equiv) were added acetic anhydride (15 equiv) and sulfuric acid (1 equiv) at 0 C. The medium was then warmed slowly to room temperature over 10 min. After 45 min, the reaction was quenched at room temperature with an aqueous solution containing sodium carbonate (30 equiv) and EtOAc (100 mL) was added.The biphasic medium was then stirred for 40 min (hydrolysis ofthe remaining acetic anhydride) and the aqueous layer was extracted twice with EtOAc. The combined organic layers were then washed with a saturated solution of NH4Cl. The organic layer was dried with anhydrous MgSO4, filtered and concentrated under vacuum. The crude residue was finally purified by flash chromatography silica gel using an appropriate gradient of a cyclohexane/EtOAc mixture as eluent to give the desired dioxinone.

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 423 - 430
[2]Tetrahedron Letters,1998,vol. 39,p. 1509 - 1512
[3]Organic Letters,2006,vol. 8,p. 3219 - 3222
[4]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196
[5]Tetrahedron Letters,2010,vol. 51,p. 6078 - 6081
[6]European Journal of Organic Chemistry,2013,p. 3316 - 3327
[7]Angewandte Chemie - International Edition,2014,vol. 53,p. 235 - 239
Angew. Chem.,2013,vol. 126,p. 239 - 243,5
[8]Journal of the American Chemical Society,2014,vol. 136,p. 15248 - 15256
[9]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3618 - 3628

9
[ 109-72-8 ]
[ 52898-49-4 ]
[ 1671-76-7 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1249 - 1255

10
[ 52898-49-4 ]
[ 591-51-5 ]
[ 4160-63-8 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1249 - 1255

11
[ 13139-86-1 ]
[ 223570-55-6 ]
[ 52898-49-4 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 1249 - 1255

12
[ 52898-49-4 ]
[ 117423-41-3 ]
2-(tert-butyl-dimethyl-silanyloxy)-1-(4-methoxy-phenyl)-2-pyridin-4-yl-ethanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2180 - 2190

14
[ 52898-49-4 ]
[ 250279-14-2 ]
[3-(4'-hydroxy-biphenyl-4-yl)-benzo[b]thiophen-2-yl]-(4-methoxy-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 1293 - 1310

15
[ 29829-22-9 ]
OC₆H₅CO₂NCH₂CH₃^(1-)*Na⁽¹⁺⁾ [ No CAS ]
[ 52898-49-4 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 1810 - 1814

16
[ 93-04-9 ]
[ 52898-49-4 ]
(3-methoxynaphthalen-2-yl)(4-methoxyphenyl)methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511
[2]Journal of Medicinal Chemistry,2008,vol. 51,p. 6138 - 6149

17
[ 6638-79-5 ]
[ 100-07-2 ]
[ 52898-49-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	EXAMPLE 3 Compound 7) N-(1-benzylpiperidin-4-yl)-7-methoxy-4-(4-methoxyphenyl)phthalazin-1-amine 3.1. N,4-dimethoxy-N-methylbenzamide; 14.7 g (151 mmol) of N,O-dimethylhydroxylamine hydrochloride are added portionwise to a solution of 25 g (147 mmol) of 4-methoxybenzoyl chloride in 450 mL of dichloromethane, stirred at 0-5 C. under nitrogen. 51 mL (370 mmol) of triethylamine are then added slowly to the mixture stirred at 0-5 C. The orange-coloured reaction medium is stirred at room temperature for 3 hours. The mixture is hydrolysed with 250 mL of water and then extracted with dichloromethane. The organic phase is washed with 100 mL of 1N HCl, 150 mL of 1N NaOH and then with water and brine. It is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 26.9 g of an orange-coloured oil are obtained, and are purified on a column of silica, eluting with dichloromethane and then with a 95/5 dichloromethane/methanol mixture. 25.4 g of a yellow oil are obtained (89% yield). LC/MS: MH+=196 (Rt=5.21 minutes) 1H NMR delta in ppm (DMSO d 6): 3.26 (s, 3H); 3.56 (s, 3H); 3.82 (s, 3H); 7.00 (d, J=8.5 Hz, 2H); 7.63 (d, J=8.5 Hz, 2H).
	With triethylamine; In dichloromethane; at 0 - 20℃; for 3h;	2.3. N-4-Dimethoxy-N-methylbenzamide To a solution of 25 g (147 mmol) of 4-methoxybenzoyl chloride in 450 mL of dichloromethane, stirred at 0-5 C. under nitrogen, are added portionwise 14.7 g (151 mmol) of N7O-dimethylhydroxylamine hydrochloride. 51 mL (370 mmol) of triethylamine are then added slowly to the mixture stirred at 0-5 C. The reaction medium is stirred at room temperature for 3 hours. The mixture is hydrolyzed with 250 mL of water and is then extracted with dichloromethane. The organic phase is washed with 100 mL of 1 N HCl, 150 mL of 1 N NaOH and then with water and with brine. It is dried over anhydrous sodium sulfate, filtered and evaporated to dryness. 26.9 g of an orange oil are obtained, which are purified on a column of silica (eluent: dichloromethane/meth-anol from 100/0 to 95/5 (v/v)). 25.4 g of a yellow oil are obtained.LC/MS: MH+=196 (Rt=5.21 minutes, pH 3.1)1H NMR (DMSO-d6, 250 MHz) delta ppm: 3.26 (s, 3H); 3.56 (s, 3H); 3.82 (s, 3H); 7.00 (d, J=8.5 Hz, 2H); 7.63 (d, J=8.5 Hz, 2H).
	With pyridine; In dichloromethane; at 0 - 20℃;	4-Methoxybenzoyl chloride ( 1.00 g, 5.86 mmol) was dissolved in DCM ( 15 mL) and cooled to 0C. N,0-dimethylhydroxlamine hydrochloride (686 mg, 7.03 mmol) and pyridine (0.57 mL, 7.03 mmol) were added, the mixture was warmed to room temperature and stirred over night.1 M hydrochloric acid and DCM were added and the phases were separated. After flash chromatographic separation N,4- dimethoxy-N-methylbenzamide (724 mg, 3.80 mmol) was obtained.

With pyridine; In dichloromethane; at 20℃; for 1h;Inert atmosphere;

General procedure: In a 50 mL round bottom flask, equipped witha magnetic stir bar and a septum, air was displaced with a continuous nitrogenflow. Then, in approximately 10 mL of dichloromethane, 1 mmol of the appropriateacylchloride and 1.1 mmol of N,O-dimethylhydroxylamine hydrochloride weredissolved and injected into the flask using a syringe . The reaction mixturewas cooled to 0C, followed by the addition of 2.2 mmol of pyridine. The resultingmixture was stirred at ambient temperature for an hour. This mixture was then partitionedbetween brine and a 1:1 mixture of ether and dichloromethane to separate theorganic layer from the aqueous layer via separation funnel. The organic layerwas dried with sodium sulfate, and filtered into an oven dried round bottomflask, using a Buchner funnel under vacuum. The solvent of the organic layerwas then removed, using a rotary evaporator, to isolate the amide product.Structure and purity were characterized by 1H NMR.

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 3073 - 3076
[2]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3337 - 3340
[3]RSC Advances,2013,vol. 3,p. 10158 - 10162
[4]Chemical Communications,2012,vol. 48,p. 9610 - 9612
[5]Patent: US2007/99895,2007,A1 .Location in patent: Page/Page column 11
[6]Journal of Medicinal Chemistry,2008,vol. 51,p. 6138 - 6149
[7]Chemistry - A European Journal,2019,vol. 25,p. 9415 - 9418
[8]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511
[9]Tetrahedron Letters,2007,vol. 48,p. 3069 - 3072
[10]Patent: US2009/124624,2009,A1 .Location in patent: Page/Page column 19
[11]Patent: WO2011/42477,2011,A1 .Location in patent: Page/Page column 40; 41
[12]Chemical Communications,2012,vol. 48,p. 8976 - 8978
[13]Tetrahedron Letters,2015,vol. 56,p. 6227 - 6230
[14]Journal of Organic Chemistry,2017,vol. 82,p. 1114 - 1126
[15]Organic Letters,2019,vol. 21,p. 7430 - 7434

18
[ 6638-79-5 ]
[ 100-09-4 ]
[ 52898-49-4 ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To a solution of acid 1 (1.0g, 8.9 mmol) in THF (15 mL) was added Et3N (3.1 mL, 22.2 mmol), and T3P (50% solution in EtOAc, 10.6mL, 17.7 mmol) at 0-5 C and the solution was stirred for about 10 min under a nitrogen atmosphere. Then N,O-dimethylhydroxylaminehydrochloride salt (1.1g, 13.3 mmol) was added to the reaction mixture at 0-5 C and the heterogeneous mixture was allowed to stir at room temperature till the completion of the reactionas indicated by TLC (see Table S-1). The mixture was then diluted with water(20 mL) followed by ethyl acetate (20 mL) and stirred for about 10 min. The separated organic layer was collected, washed with 5% citric acid (2 x10 mL),5% Na2CO3 (2 x 10 mL), and then brine solution. The collected organic layer was dried over anhydrous Na2SO4, filtered and concentrated under low vacuum. The crude product obtainedwas purified by flash column chromatography over silicagel (100-200 mesh) using 12-15% EtOAc / n-hexane as eluent to affordthe desired compound.
86%		To 4-methoxybenzoic acid (100 g, 657.89 mmol) was added SOCl2 (200 g, 1.68 mol). To the solution was added a solution of N-methoxymethanamine hydrochloride (71.5 g, 729.59 mmol) in 500 mL of DCM. The mixture was stirred 2 hours with refluxing. To the mixture was added Et3N (300 g, 2.97 mol). The solution was allowed to react, with stirring, for 30 minutes while the temperature was maintained at room temperature. When the reaction was completed, it was quenched by 500 mL water and extracted by DCM. Removal of solvent followed by purification by flash column chromatography on silica gel gave 110 g (86%) of N,4-dimethoxy-N-methylbenzamide as a yellow liquid.
81%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 3h;	General procedure: To a solution of 3-cyanobenzoic acid 8a (3.0 g, 19.7 mmol) in DMF was added N,O-dimethylhydroxylamine hydrochloride (2.0 g, 20.7 mmol), Et3N (2.88 mL, d = 0.73, 20.7 mmol) and EDC·HCl (4.0 g, 20.7 mmol). After the mixture was stirred for 3 h at room temperature, the solvent was removed in vacuo and the residue was dissolved in EtOAc, washed with 10% citric acid, 10% NaHCO3 and saturated NaCl, and dried over Na2SO4. Then, the solvent was removed to give a colorless oil of compound 9a (3.0 g, 79%).

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7850 - 7864
[2]Synthetic Communications,2003,vol. 33,p. 4013 - 4018
[3]Tetrahedron Letters,2016,vol. 57,p. 3924 - 3928
[4]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 171 - 173
[5]Angewandte Chemie - International Edition,2015,vol. 54,p. 14017 - 14021
Angew. Chem.,2015,vol. 127,p. 14223 - 14227,5
[6]Patent: US9604978,2017,B2 .Location in patent: Page/Page column 196-197
[7]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4279 - 4289
[8]Tetrahedron Letters,2009,vol. 50,p. 781 - 784

19
[ 1578-33-2 ]
[ 52898-49-4 ]
(4-methoxy-phenyl)-(5-trimethylsilanyl-furan-2-yl)-methanone [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2357 - 2359

20
[ 121-98-2 ]
[ 6638-79-5 ]
[ 52898-49-4 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2357 - 2359

21
[ 52898-49-4 ]
[ 623-47-2 ]
(E)-2-(N-methoxy-N-methyl-amino)-4-oxo-4-(4-anisoyl)-2-butenoic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 3219 - 3222

22
[ 104-92-7 ]
[ 201230-82-2 ]
[ 6638-79-5 ]
[ 52898-49-4 ]

Reference： [1]Organic Letters,2006,vol. 8,p. 4843 - 4846
[2]Journal of Organic Chemistry,2008,vol. 73,p. 7102 - 7107
[3]RSC Advances,2014,vol. 4,p. 30019 - 30027

23
[ 60986-88-1 ]
[ 52898-49-4 ]
[ 60986-77-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196

24
[ 6089-04-9 ]
[ 52898-49-4 ]
[ 937791-08-7 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3069 - 3072

25
[ 52898-49-4 ]
[ 3761-92-0 ]
[ 69287-13-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 7850 - 7864

26
[ 52898-49-4 ]
C₁₆H₂₁NO₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 3069 - 3072

27
[ 52898-49-4 ]
VUSC₀₀₁ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196

28
[ 100-09-4 ]
[ 52898-49-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 193 - 196
[2]Tetrahedron,2012,vol. 68,p. 5415 - 5421
[3]European Journal of Organic Chemistry,2013,p. 3316 - 3327
[4]Journal of the American Chemical Society,2014,vol. 136,p. 15248 - 15256
[5]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 3618 - 3628
[6]Journal of Organic Chemistry,2017,vol. 82,p. 1114 - 1126

29
[ 52898-49-4 ]
C₃₀H₃₆O₄Si₂ [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2357 - 2359

30
[ 52898-49-4 ]
C₃₀H₃₆O₄Si₂ [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2357 - 2359

31
[ 52898-49-4 ]
[ 342044-96-6 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

32
[ 52898-49-4 ]
[3'-benzoyl-2,2'-dihydroxy-1,1'-binaphthalenyl-3-yl]-phenyl-methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

33
[ 52898-49-4 ]
(3'-benzoyl-2,2'-dihydroxy-[1,1']binaphthalenyl-3-yl)-(4-methoxy-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

34
[ 52898-49-4 ]
(3'-benzoyl-2,2'-dihydroxy-[1,1']binaphthalenyl-3-yl)-(4-methoxy-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

35
[ 52898-49-4 ]
[2,2'-dihydroxy-3'-(4-methoxy-benzoyl)-[1,1']binaphthalenyl-3-yl]-(4-methoxy-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

36
[ 52898-49-4 ]
[2,2'-dihydroxy-3'-(4-methoxy-benzoyl)-[1,1']binaphthalenyl-3-yl]-(4-methoxy-phenyl)-methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511
[2]Journal of Organic Chemistry,2003,vol. 68,p. 5500 - 5511

37
[ 52898-49-4 ]
4-[5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-yl]-pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 2180 - 2190

38
[ 52898-49-4 ]
[ 132160-44-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 459 - 464
[2]Tetrahedron Letters,1994,vol. 35,p. 2919 - 2920

39
[ 52898-49-4 ]
[ 175791-64-7 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 459 - 464
[2]Tetrahedron Letters,1994,vol. 35,p. 2919 - 2920

40
[ 52898-49-4 ]
[ 175791-65-8 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 459 - 464
[2]Tetrahedron Letters,1994,vol. 35,p. 2919 - 2920

41
[ 52898-49-4 ]
[ 175791-66-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1996,p. 459 - 464
[2]Tetrahedron Letters,1994,vol. 35,p. 2919 - 2920

42
[ 52898-49-4 ]
[ 147580-37-8 ]

Reference： [1]Chimia,1995,vol. 49,p. 381 - 385

43
[ 52898-49-4 ]
[ 147030-67-9 ]

Reference： [1]Chimia,1995,vol. 49,p. 381 - 385

44
[ 52898-49-4 ]
[ 615277-24-2 ]

Yield	Reaction Conditions	Operation in experiment
41%		5-bromo-3- (3-chlorophenyl)-2, 1-benzisoxazole (0.13 m) was added at-70C to THF (300ml) under N2 flow. A solution of BuLi (0.143 mol) was added dropwise. The mixture was stirred at-70C for 10 minutes. A solution of N, 4-dimethoxy-N-methyl- benzamide (0.117 mol) in THF (100ml) was added dropwise at-70C. The mixture was stirred at-70C for 1 hour, poured out on ice/EtOAc and extracted with EtOAc. The organic layer was separated, dried (MgS04), filtered, and the solvent was evaporated. The residue was crystallized from diethyl ether. The precipitate was filtered off and dried under a vacuo, yielding 19.5g (41%) of [3- (3-chlorophenyl)-2, 1-benzisoxazol-5- yl] (4-methoxyphenyl)- methanone (intermediate 10).

Reference： [1]Patent: WO2003/87101,2003,A1 .Location in patent: Page/Page column 25

45
[ 52898-49-4 ]
[ 3400-22-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium metal trapped in the nanoscale pores of silica gel; In tetrahydrofuran; at 20℃; for 2h;Glovebox; Sealed tube; Inert atmosphere;	General procedure: In a helium-filled glove box, the desired number ofequivalents of Na-AG or Na-SG were added to a round bottom flask, along with aglass-coated stir bar, and the flask sealed with a septum. This closed systemwas then taken out of the glove box, continuously purged with nitrogen, followedby injection of the pure synthesized Weinreb amide dissolved in THF. The resulting mixture was stirred for thetime specified. After completion of the reaction, the mixture was then partitioned using ethyl acetate and brine. The organic layer was concentrated under reducedpressure using a rotary evaporator. 1H NMR of the crude product wastaken to check for reaction extent/completion and to identify the productsobtained. Crude product was fractionated and purified by columnchromatography on silica gel to afford the desired product and byproducts.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6227 - 6230
[2]Synlett,2008,p. 2132 - 2136
[3]Journal of Organic Chemistry,2017,vol. 82,p. 6528 - 6540

46
[ 766-11-0 ]
[ 52898-49-4 ]
[ 1125674-13-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 781 - 784

47
[ 372-48-5 ]
[ 52898-49-4 ]
[ 79574-74-6 ]
[ 3400-22-4 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 781 - 784

48
[ 52898-49-4 ]
[ 22921-68-2 ]
[ 108837-29-2 ]

Yield	Reaction Conditions	Operation in experiment
64%		3.2. 5-methoxy-2-(4-methoxybenzoyl)benzoic acid; A solution of 18.5 g (80 mmol) of 2-bromo-5-methoxybenzoic acid in 150 mL of tetrahydrofuran is stirred under nitrogen at -78 C. in a bath of cardice/acetone. 100 mL (160 mmol) of a 1.6M solution of n-butyllithium in hexane are added dropwise over about 1 hour, while taking care to ensure that the temperature does not exceed -70 C. About half way through the introduction, the formation of a beige-coloured precipitate that corresponds to the formation of the lithium carboxylate is noted. After the addition, the mixture is stirred at -78 C. for 1 hour, and a solution of 15.9 g (80 mmol) of N,4-dimethoxy-N-methylbenzamide in 20 mL of THF is added dropwise. The reaction medium is stirred at -78 C. for 1 hour and the bath of cardice/acetone is then removed and the reaction medium is stirred, while allowing the temperature to return gradually to room temperature, for 18 hours. The mixture is hydrolysed with 100 mL of water, basified to pH =12 with 2N NaOH solution and then extracted with tert-butyl methyl ether. The aqueous phase containing the carboxylate is acidified with 5N HCl solution to pH 1 and extracted with dichloromethane. The dichloromethane phase is washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The product is crystallized from isopropyl ether; after filtering and drying, 14.6 g of white crystals are obtained (yield=64%). m.p.=170 C. (Mettler FP62) LC/MS: MH+=287 (Rt=7.07 minutes) 1H NMR delta in ppm (DMSO d 6): 3.85 (s, 3H); 3.90 (s, 3H); 7.03 (d, J=8.5 Hz, 2H); 7.24 (dd, J1=8.5 Hz, J2=2.5 Hz, 1H); 7.35 (d, J=8.5 Hz, 1H); 7.42 (d, J=2.5 Hz, 1H); 7.61 (d, J=8.5 Hz, 2H); 13.1 (s, 1H, COOH).
		2.4. 5-Methoxy-2-(4-methoxybenzoyl)benzoic Acid A solution of 18.5 g (80 mmol) of 2-bromo-5-methoxybenzoic acid in 150 mL of THF is stirred under nitrogen at -78 C. 100 mL (160 mmol) of a 1.6 M solution of n-butyllithium in hexane are added dropwise over about one hour while taking care to ensure that the temperature does not exceed -70 C. After the addition, the mixture is stirred at -78 C. for one hour, and a solution of 15.9 g (80 mmol) of N-4-dimethoxy-N-methylbenzamide in 20 mL of THF is then added dropwise. The reaction medium is stirred at -78 C. for one hour and then at room temperature for 18 hours. The mixture is hydrolyzed with 100 mL of water, basified to pH=12 with 2 N NaOH solution and extracted with tert-butyl methyl ether. The aqueous phase containing the carboxylate is acidified with 5 N HCl solution to pH=1 and extracted with dichloromethane. The dichloromethane phase is washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated. The product is crystallized from isopropyl ether; after filtering off and drying, 14.6 g of white crystals are obtained.m.p.=170 C. (M)LC/MS: MH+=287 (Rt=7.07 minutes, pH 3.1)1H NMR (DMSO-d6, 250 MHz) delta ppm: 3.85 (s, 3H); 3.90 (s, 3H); 7.03 (d, J=8.5 Hz, 2H); 7.24 (dd, J1=8.5 Hz, J2=2.5 Hz, 1H); 7.35 (d, J=8.5 Hz, 1H); 7.42 (d, J=2.5 Hz, 1H); 7.61 (d, J=8.5 Hz, 2H); 13.1 (s, 1H, COOH).

Reference： [1]Patent: US2007/99895,2007,A1 .Location in patent: Page/Page column 11
[2]Patent: US2009/124624,2009,A1 .Location in patent: Page/Page column 19

49
[ 1513-65-1 ]
[ 52898-49-4 ]
[ 1158955-22-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 2293 - 2297

50
[ 3469-26-9 ]
[ 52898-49-4 ]
C₂₀H₁₈O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 6138 - 6149

51
[ 75-77-4 ]
[ 52898-49-4 ]
[ 508191-77-3 ]
[ 1186220-86-9 ]

Reference： [1]Synthetic Communications,2009,vol. 39,p. 2852 - 2858

52
[ 1062512-43-9 ]
[ 100-09-4 ]
[ 52898-49-4 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 4474 - 4477

53
[ 5720-07-0 ]
[ 30289-28-2 ]
[ 2132-80-1 ]
[ 52898-49-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1251 - 1258

54
[ 5720-07-0 ]
[ 30289-28-2 ]
[ 52898-49-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1251 - 1258

55
[ 30289-28-2 ]
potassium 4-(methoxy)phenyltrifluoroborate [ No CAS ]
[ 52898-49-4 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 1251 - 1258

56
[ 52898-49-4 ]
[ 1826-67-1 ]
[ 100-46-9 ]
[ 144172-58-7 ]

Reference： [1]Heterocycles,2010,vol. 80,p. 679 - 687

57
[ 14001-63-9 ]
[ 52898-49-4 ]
[ 875757-74-7 ]

Reference： [1]Monatshefte fur Chemie,2009,vol. 140,p. 423 - 430

58
[ 52898-49-4 ]
[ 115-19-5 ]
4-hydroxy-1-(4-methoxyphenyl)-4-methyl-2-pentyn-1-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 2123 - 2126

59
[ 52898-49-4 ]
[ 1826-67-1 ]
[ 7448-86-4 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 3073 - 3076

60
[ 52898-49-4 ]
[ 106-96-7 ]
[ 196952-70-2 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 6078 - 6081

61
[ 104-92-7 ]
[ 14040-11-0 ]
[ 6638-79-5 ]
[ 52898-49-4 ]
[ 3400-22-4 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 978 - 981

62
[ 696-62-8 ]
[ 6638-79-5 ]
[ 13939-06-5 ]
[ 52898-49-4 ]

Reference： [1]Australian Journal of Chemistry,2017,vol. 70,p. 44 - 51
[2]Journal of Organic Chemistry,2011,vol. 76,p. 978 - 981

63
[ 52898-49-4 ]
(1,3-dioxan-2-yl)ethylmagnesium bromide [ No CAS ]
[ 121789-38-6 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at -78 - 20℃;	N,4-dimethoxy-N-methylbenzamide (500 mg, 2.56 mmol) were dissolved in THF and cooled to -78C. (2-(l ,3-Dioxan-2-yl)ethyl)magnesium bromide (0.5 M solution in THF, 12.8 mL, 6.40 mmol) were added and the mixture was allowed to reach room temperature over night. 1 M hydrochloric acid and DCM were added and the phases were separated. After flash chromatographic separation 3-(l,3- dioxan-2-yl)-l -(4-methoxyphenyl)propan-l-one (625 mg, 2.50 mmol) was obtained.

Reference： [1]Patent: WO2011/42477,2011,A1 .Location in patent: Page/Page column 40; 41

64
[ 52898-49-4 ]
[ 1289206-94-5 ]

Reference： [1]Patent: WO2011/42477,2011,A1

65
[ 52898-49-4 ]
[ 1289206-93-4 ]

Reference： [1]Patent: WO2011/42477,2011,A1

66
[ 52898-49-4 ]
[ 874-90-8 ]