[ CAS No. 932-96-7 ] {[proInfo.proName]}

Name: 932-96-7|4-Chloro-N-methylaniline|97%
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SKU: A122749
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Quality Control of [ 932-96-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 932-96-7 ]

CAS No. :	932-96-7	MDL No. :	MFCD00000614
Formula :	C₇H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XCEYKKJMLOFDSS-UHFFFAOYSA-N
M.W :	141.60	Pubchem ID :	70272
Synonyms :

Calculated chemistry of [ 932-96-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	40.76
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	2.84
Log Po/w (WLOGP) :	2.19
Log Po/w (MLOGP) :	2.41
Log Po/w (SILICOS-IT) :	2.16
Consensus Log Po/w :	2.3

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.93
Solubility :	0.165 mg/ml ; 0.00116 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.251 mg/ml ; 0.00177 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.43
Solubility :	0.0531 mg/ml ; 0.000375 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 932-96-7 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P261-P273-P280-P305+P351+P338	UN#:	2924
Hazard Statements:	H225-H318-H335-H412	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 932-96-7 ]

* 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 [ 932-96-7 ]
Downstream synthetic route of [ 932-96-7 ]

[ 932-96-7 ] Synthesis Path-Upstream 1~4

1
[ 131543-46-9 ]
[ 932-96-7 ]
[ 60434-13-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 20, p. 3484 - 3489

2
[ 932-96-7 ]
[ 15249-31-7 ]
[ 2058-74-4 ]
[ 108726-52-9 ]
[ 26772-93-0 ]
[ 15950-17-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 17, p. 3391 - 3400

3
[ 932-96-7 ]
[ 15950-17-1 ]

Reference： [1] Chemische Berichte, 1898, vol. 31, p. 2535
[2] Chemische Berichte, 1898, vol. 31, p. 2535

4
[ 64-17-5 ]
[ 932-96-7 ]
[ 7782-77-6 ]
[ 15950-17-1 ]

Reference： [1] Chemische Berichte, 1898, vol. 31, p. 2535

[ 932-96-7 ] Synthesis Path-Downstream 1~75

1
[ 3622-23-9 ]
[ 932-96-7 ]
[ 101095-17-4 ]

Reference： [1]Journal of the Chemical Society,1958,p. 1561,1565

2
[ 932-96-7 ]
[ 15950-17-1 ]
4-chloro-N-methyl-2,6-dinitro-N-nitroso-aniline [ No CAS ]

Reference： [1]Chemische Berichte,1898,vol. 31,p. 2535
[2]Chemische Berichte,1898,vol. 31,p. 2535

3
[ 106-47-8 ]
[ 74-88-4 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
97%	With C24H52B20Cl2Rh2Se2; In toluene; at 20℃; for 2.5h;	Using the rhodium complex Rh prepared in Example 1 as a catalyst,Catalyzes N-methylation of aromatic amines:To 4-chloroaniline (10 mmol, 1.27 g) and CH3I (10 mmol, 1.42 g) was added a toluene solution of a binuclear semi-sandwich rhodium complex (0.01 mmol, 9.9 mg) containing ortho carborane,The reaction temperature is room temperature and the reaction time is 150 minutes.After the completion, the concentrated reaction solution was directly separated by silica gel column chromatography and dried to the same quality.The corresponding N-methylated product C7H8ClN was obtained (yield 97%),
85%		General procedure: To a solution of aniline (5 mmol) in THF (10 mL) at -78 C was added MeLi (1.1M in diethyl ether solution, 5mmol) dropwise over 1 hour and the mixture was stirred for 30 minutes. Iodomethane (6.6 mmol) in THF (2.0 mL)was added dropwise to the reaction mixture. The reaction mixture was stirred for 1 hour and allowed to be warmed to room temperature and stirred for 2 hours. After the reaction was completed, saturated aqueous NH4Cl was addedand the mixture was extracted with EtOAc (3 x 60 mL). The combined organic layers were washed with brine and dried over Na2SO4. Solvent was then removed under reduced pressure and the residue was purified by columnc hromatography to afford corresponding product.
55%	With potassium carbonate; In water; acetonitrile; at 50℃; for 2h;	A mixture of 4-chloroaniline (1.27 g, lOmmol), methyl iodide (1.24 g, lOmmol), potassium carbonate (1.38 g, lOmmol) Was dissolved in acetonitrile (25 mL) and heated to 50 C for 2 hours. Water (100 mL) was added, extracted with dichloromethane (200 mL) The organic phase was washed three times with water, dried, dried and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 5: 1) (0.78 g, yield 55%).

With N-ethyl-N,N-diisopropylamine; In toluene; at 90℃; for 18h;

General procedure: A mixture of asubstituted aniline (33aem) (5.5 mmol), N-ethyldiisopropylamineand alkyl halide (34aec) or ethyl sulfate (34d) in the molar ratio of1:1:1 in toluene (21 ml) was stirred and heated at 90?C for 18 h. Inthe cases listed below it was necessary to vary the conditions of reaction as summarized in Table 1.The resulting suspension was taken up with ethyl acetate. The organic phase was washed with water then dried over anhydrous sodium sulfate. On evaporation of the solvent, in most cases a solidor an oily residuewas obtained. Purification was performed by flash chromatography on a silica gel column eluting with the following mixture of solvents: ethyl acetate/petrol ether 40-60?, in the ratio of 6:4 (35, 42); 7:3 (52); 8:2 (41, 43, 48, 51, 53, 62, 65); 9:1 (38, 39,45, 46, 47, 50); 95:5 (36, 37, 44, 55, 56, 57, 58, 59, 60, 61); 98:2 (64);petrol ether 40-60?/diethyl ether 9:1 (49); toluene/ethyl acetate 95:5 (63); chloroform/methanol 95:5 (54), chloroform/methanol 98:2 (66).

Reference： [1]Patent: CN110240620,2019,A .Location in patent: Paragraph 0047-0050
[2]Synthesis,2018,vol. 50,p. 2981 - 2989
[3]Heterocycles,2006,vol. 68,p. 11 - 22
[4]Patent: CN106316975,2017,A .Location in patent: Paragraph 0274-0276
[5]Chemische Berichte,1898,vol. 31,p. 2535
[6]European Journal of Medicinal Chemistry,2014,vol. 75,p. 169 - 183

4
[ 112160-74-4 ]
[ 100-61-8 ]
[ 932-96-7 ]
[ 932-32-1 ]

Reference： [1]Journal of the Chemical Society,1901,vol. 79,p. 465

5
[ 34253-02-6 ]
[ 124-38-9 ]
[ 932-96-7 ]
[ 132368-92-4 ]
[ 132368-94-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1645 - 1647

6
[ 698-69-1 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
63%		General procedure: A round-bottom flask was chargedwith N,N-dialkyl aniline dissolved in toluene solution, under N2 condition. TBHP was added drop wise and reaction was stirred for 2 min. Triethylamine was added thereafter, and then the contents of the reaction were stirred for 3 h at 110 C under inert N2 condition. The reaction mixture was washed 2-3 times with H2O and ethyl acetate. The upper organic layer was separated and dried over sodium sulphate and then subjected to rotavapour. The crude mixture was purified by column chromatography on silica gel (60-120).

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 3548 - 3550
[2]Journal of Chemical Sciences,2016,vol. 128,p. 1469 - 1473
[3]Journal of the Chemical Society. Perkin transactions I,1980,p. 828 - 832

7
[ 698-69-1 ]
[ 932-96-7 ]
[ 57649-14-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 3% 2: 10%	With dihydrogen peroxide; oxygen; iron(II) sulfate In sulfuric acid; water Ambient temperature; pH=2; further objects: pH-dependence (1.8), different substrate concentrations;

Reference： [1]Galliani, Guido; Rindone, Bruno [Gazzetta Chimica Italiana, 1983, vol. 113, # 3/4, p. 207 - 212]

8
[ 124-38-9 ]
[ 932-96-7 ]
[ 34231-77-1 ]
[ 132368-98-0 ]
[ 132368-96-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1645 - 1647

9
[ 62001-32-5 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With lithium aluminium tetrahydride In tetrahydrofuran for 0.5h;

Reference： [1]Katritzky, Alan R.; Rachwal, Stanislaw; Rachwal, Bogumila [Journal of the Chemical Society. Perkin transactions I, 1987, p. 805 - 810]

10
[ 2617-79-0 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature;
	Multi-step reaction with 2 steps 1: anhydrous potassium carbonate, sodium hydroxide, tetrabutylammmonium hydrogensulphate / benzene / 1 h / 5 - 10 °C / Heating 2: water / Heating

Reference： [1]Rosowsky, Andre; Forsch, Ronald A.; Queener, Sherry F. [Journal of Medicinal Chemistry, 1995, vol. 38, # 14, p. 2615 - 2620]
[2]Sharma, V. K.; Kumar, A.; Agarwal, K. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 11, p. 1153]

11
[ 67-56-1 ]
N-(methylphenylamino)-2,4,6-trimethylpyridinium tetrafluoroborate [ No CAS ]
[ 932-96-7 ]
[ 932-32-1 ]
[ 100-61-8 ]
[ 5961-59-1 ]

Reference： [1]Journal of Physical Organic Chemistry,1997,vol. 10,p. 917 - 924

12
[ 100-61-8 ]
[ 932-96-7 ]
[ 932-32-1 ]

Reference： [1]Synthetic Communications,1998,vol. 28,p. 1891 - 1896

13
N-(methylphenylamino)-2,4,6-trimethylpyridinium tetrafluoroborate [ No CAS ]
[ 108-75-8 ]
[ 932-96-7 ]
[ 932-32-1 ]
[ 62-53-3 ]

Reference： [1]Journal of Physical Organic Chemistry,1997,vol. 10,p. 917 - 924

14
[ 64-17-5 ]
[ 932-96-7 ]
[ 7782-77-6 ]
[ 15950-17-1 ]
4-chloro-N-methyl-2,6-dinitro-N-nitroso-aniline [ No CAS ]

Reference： [1]Chemische Berichte,1898,vol. 31,p. 2535

15
[ 7647-01-0 ]
[ 77102-32-0 ]
[ 932-96-7 ]
[ 932-32-1 ]
[ 107-02-8 ]
[ 100-61-8 ]

Reference： [1]Chemische Berichte,1919,vol. 52,p. 1673

16
[ 1220-00-4 ]
[ 932-96-7 ]
[ 106-47-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 49% 2: 48%	With sodium tetrahydroborate; nickel dichloride In methanol at 20℃; for 1h;

Reference： [1]Khurana, Jitender M.; Kukreja, Gagan; Bansal, Geeti [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 22, p. 2520 - 2524]

17
[ 932-96-7 ]
[ 248282-13-5 ]
N-methyl-N-(4-chloro-phenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxo-quinoline-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	In toluene for 6h; Heating;

Reference： [1]Jönsson, Stig; Andersson, Gunnar; Fex, Tomas; Fristedt, Tomas; Hedlund, Gunnar; Jansson, Karl; Abramo, Lisbeth; Fritzson, Ingela; Pekarski, Olga; Runström, Anna; Sandin, Helena; Thuvesson, Ingela; Björk, Anders [Journal of Medicinal Chemistry, 2004, vol. 47, # 8, p. 2075 - 2088]

18
[ 932-96-7 ]
[ 309-91-1 ]
4-[(4-chloro-phenyl)-methyl-amino]-N,N-diethyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: N-methyl(p-chloroaniline) With n-butyllithium In tetrahydrofuran; hexane cooling; Stage #2: N,N-diethyl-4-fluorobenzenesulfonamide In tetrahydrofuran; hexane at 20℃;

Reference： [1]Badetti, Elena; Moreno-Mañas, Marcial; Pleixats, Roser; Sebastián, Rosa M.; Serra, Anna; Soler, Roger; Vallribera, Adelina [Synlett, 2005, # 3, p. 449 - 452]

19
[ 611-35-8 ]
[ 932-96-7 ]
[ 850807-89-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With acetic acid at 130 - 135℃; for 3h;
97%	Stage #1: 4-chloroquinoline; N-methyl(p-chloroaniline) With acetic acid for 3h; Heating / reflux; Stage #2: With sodium hydroxide In water	Compound VIII A A solution of 4-chloroquinoline (5 mmol) and of 4-chloro-N-methylaniline (10 mmol) in glacial acetic acid (15 ml) was heated with reflux for 3 h under a stream of argon. After cooling, the solution was basified with a 10% NaOH solution until pH = 10 and the resulting suspension was concentrated in a rotary evaporator and purified by means of flash chromatography (9:1, CH2Cl2:MeOH) to give the target molecule as a yellowish syrup (97%). 1H-NMR (400 MHz, CDCl3): d 8.10 (d, J = 8.5, 1H, H-2quin); 7.70 (d, J = 8.5, 1H, H-5quin); 7.65 (t, J = 7.9, 1H, H-7quin); 7.38 (t, J = 8.5, 1H, H-6quin); 7.35 (d, J = 7.9, 1H, H-8quin); 7.17 (d, J = 8.9, 2H, H-3,5anil); 7.14 (d, J = 8.5, 1H, H-3quin); 6.76 (d, J = 8.9, 2H, H-2,6anil); 3.45 (s, 6H, Me). 13C-NMR (100 MHz, CDCl3): d 153.37 (C-4quin); 151.16 (C-2quin); 150.01 (C-1anil); 148.17 (C-8aquin); 135.02 (C-4anil); 130.07 (C-7quin); 129.52 (C-6quin); 129.29 (C-3,5anil); 126.26(C-4aquin); 126.07 (C-5quin); 124.40 (C-8quin); 119.79 (C-2,6anil); 115.08 (C-3quin); 41.75 (Me). HRMS (m/z): Calculated for C16H13N2Cl [(M + H)]+ 269.0845. Found: 269.0845. Analysis for C16H13N2Cl. Calculated: C 71.51; H 4.88; N 10.42%. Found: C 71.60; H 4.71; N 10.33%.

Reference： [1]Sánchez-Martín, Rosario; Campos, Joaquín M.; Conejo-García, Ana; Cruz-López, Olga; Báñez-Coronel, Mónica; Rodríguez-González, Agustín; Gallo, Miguel A.; Lacal, Juan C.; Espinosa, Antonio [Journal of Medicinal Chemistry, 2005, vol. 48, # 9, p. 3354 - 3363]
[2]Current Patent Assignee: UNIVERSITY OF GRANADA; GOVERNMENT OF SPAIN - EP1710236, 2006, A1 Location in patent: Page/Page column 14

20
[ 10130-89-9 ]
[ 932-96-7 ]
[ 668261-31-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol; at 0 - 20℃; for 5.5h;	A solution [OF 4-CHLORO-N-METHYLANILINE] (10.0 g, 0.0706 mol, 1.1 eq) and triethylamine (7.78 g, 0.0770 mol, 1.2 eq) in 140 [ML] of methanol, cooled in an ice bath at [0-5C,] was treated portionwise over a one minute period with solid [4-CBLOROSULFONYL] benzoic acid (14.2 g, 0.0642 mol, [1.] Oeq). After the addition was complete, the cooling bath was removed and the reaction mixture was stirred under a nitrogen atmosphere while warming to room temperature on its own. After 5.5 h, the contents were poured into 270 [ML] of ice water containing 130 mL [OF 3 N NAOH,] washed the milky solution with methylene chloride (2 X 100 mL), acidified the aqueous layer with 35 [ML] of concentrated HCI. After cooling the mixture in an ice bath, the white precipitated product was collected and dried in a vacuum oven at [70C] overnight to yield 14.92 g (71%) [OF 2. 1H NMR (DMSO-D6) 6] 13.53 (brs, 1 H), 8. 11 (dd, [J= 2, 7 HZ, 2 H),] 7.63 (dd, J= 2,7 Hz, 2 [H),] 7.42 (dd, J= 2,7 Hz, 2 H), 7.14 (dd, J= 2,7 Hz, 2 H), 3.15 (s, 3 [H)] ppm

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 6173 - 6177
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4040 - 4043
[3]Patent: WO2004/18414,2004,A2 .Location in patent: Page 58
[4]Patent: WO2004/18414,2004,A2 .Location in patent: Page 58-59

21
[ 932-96-7 ]
[ 4025-64-3 ]
[ 361473-14-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With pyridine; In ethyl acetate; at 0 - 20℃;	General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2×) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.
	With triethylamine; In methanol; at 0 - 20℃; for 5.5h;	A chilled solution of <strong>[932-96-7]4-chloro-N-methylaniline</strong> (2.77 g, 19.6 mmol, Aldrich) and triethylamine (2.2 mL, 16 mmol) in methanol (10 mL) was added by cannula to solid [3-(chlorosulfonyl)] benzoic acid (2.87 g, 13.0 mmol, Aldrich) with stirring in an ice bath. The ice bath was removed after 45 minutes, and the mixture was stirred at room temperature for 4.75 hours. The mixture was added to a separatory funnel with 60 mL of 1 M aqueous KOH, and this solution was washed with 2 X 60 mL [OF CH2CL2.] The aqueous layer was then acidified with concentrated HC1. The resulting precipitate was collected, washed with water, and recrystallized from hot toluene. The crystals were collected, washed with pentane, and dried at [100 C] under vacuum. Yield was 2.48 g of white solid.
	In dichloromethane; at 0 - 20℃; for 12h;	General procedure:To a solution of 3-(chlorosulfonyl)benzoic acid (1.0 equiv, ca. 0.1 M) in dichloromethane, 4-bromo-N-methylaniline (3.1 equiv) was slowly added at 0 C with stirring. The mixture was stirred at room temp for 12 h. The solvent was removed with a nitrogen gas stream, the mixture was treated with 1 M NaOH (> 10 equiv), and was extracted with ether three times. The aqueous fraction was then acidified with 3 M HCl to pH ~1. The mixture turned cloudy during the addition. The resulting precipitate was collected by suction filtration on a Buchner funnel, washed with distilled water, and dried overnight at reduced pressure to give 3-(N-(4-bromophenyl)-N-methylsulfamoyl)benzoic acid (7a, 50-60%), which was used without further purification. To a solution of 7a (1.0 equiv, ca. 0.1 M), was added <strong>[932-96-7]4-chloro-N-methylaniline</strong> (1.1 equiv), EDCI (1.3 equiv), and DMAP (0.1 equiv). The mixture was stirred at room temp for 12 h and then diluted with excess EtOAc. The organic mixture was washed with 1 M aqueous HCl (2 times), 1 M aqueous NaHCO3 (2 times), and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to yield a crude product, which was purified by silica gel column chromatography to give 3a as a thick gel.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 414 - 426
[2]Patent: WO2004/18461,2004,A2 .Location in patent: Page 22; 24-25
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2789 - 2793

22
[ 932-96-7 ]
[ 7126-57-0 ]
4-[[(4-chlorophenyl)-methylamino]methyl]-1H-pyrrole-2-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		4-chloro-N-methylaniline (0.225 mL, 1.86 mmol) was added to a stirring, room temperature solution of 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.2585 g, 1.55 mmol) in 5% acetic acid in methanol under N2. After stirring at room temperature for 30 minutes, sodium cyanoborohydride (0.1585 g, 2.52 mmol) was added, and the reaction was stirred at room temperature overnight. About 3 mL of saturated K2CO3 were added, and the reaction was extracted twice with ethyl acetate. The combined organics were washed with saturated NaHCO3 (4 mL) and brine (4 mL), then the combined organics were dried with Na2SO4, filtered and concentrated en vacuo. The crude product was purified by silica gel chromatography (Combiflash column, 85:15 Hexanes:Ethyl acetate) to obtain 0.3419 g (76%) of 4-[(4-chlorophenyl)-methylamino]methyl]-1H-pyrrole-2-carboxylic acid ethyl ester (191) as a light tan solid. Note: Starting material 4-formyl-1H-pyrrole-2-carboxylic acid ethyl ester has an HPLC retention time=7.337 min. HPLC: 8.478 min.

Reference： [1]Patent: US2005/143443,2005,A1 .Location in patent: Page/Page column 70-71

23
[ 693-98-1 ]
[ 13162-26-0 ]
[ 932-96-7 ]
2-(N-methyl-4-chloroanilino)-4-(2-methylimidazolyl)-6-methyl-5-nitropyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In tetrahydrofuran; ethanol; hexane;	Example 4 2-(N-methyl-4-chloroanilino)-4-(2-methylimidazolyl)-6-methyl-5-nitropyrimidine (g). To a stirred, cold (-78 C.) solution of <strong>[13162-26-0]2,4-dichloro-6-methyl-5-nitropyrimidine</strong> (207.5 mg, 1.0 mmol, 1.0 equiv.) in THF (2.25 mL) and EtOH (2.25 mL) was added 2-methylimidazole (164 mg, 2.00 mmol, 2.0 equiv.) in a solution of EtOH (2.25 mL) dropwise. After 45 min., the dry ice bath was replaced with a water ice bath and stirring was continued for an additional 2 h and 15 min. 4-Chloro-N-methylaniline (0.485 mL, 4.0 mmol, 4.0 equiv.) was then added and the reaction solution was stirred for 2 h and 40 min. Solvent was removed by evaporation and the residue was diluted with dichloromethane, washed three times with 0.1 M HCl, three times with saturated aqueous NaCl solution and dried over MgSO4. Solvent was removed from the organic phase and the residue was purified by silica gel chromatography (1:1 hexane/diethyl ether, 1% AcOH as eluant) to provide g (55.9 mg, 15.6%).

Reference： [1]Patent: US2003/130264,2003,A1

24
[ 932-96-7 ]
[ 3697-66-3 ]
[ 541-41-3 ]
ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	triethylamine;	EXAMPLE XXXV Preparation of ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate 1-Carboethoxycyclopropanecarboxylic acid (5.54 grams, 0.035 mole), ethyl chloroformate (3.80 grams, 0.035 mole) and 4-chloro-N-methylaniline (4.96 grams, 0.035 mole) were reacted sequentially in the presence of triethylamine (3.54 grams, 0.035 mole) in a manner similar to that described in Example XXXIII to give 2.26 grams (0.008 mole) of ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate having a melting point of 53 C.-56.5 C. NMR analysis of the product indicated the following: NMR (CDCl3): delta 1.0-1.46 (m,7H), 3.35 (s,3H), 3.7-4.2 (m,2H), 7.0-7.47 (m,4H) ppm.
	triethylamine;	EXAMPLE XXXV Preparation of ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate 1-Carboethoxycyclopropanecarboxylic acid (5.54 grams, 0.035 mole), ethyl chloroformate (3.80 grams, 0.035 mole) and 4-chloro-N-methylaniline (4.96 grams, 0.035 mole) were reacted sequentially in the presence of triethylamine (3.54 grams, 0.035 mole) in a manner similar to that described in Example XXXIII to give 2.26 grams (0.008 mole) of ethyl 1-[N-(4-chlorophenyl)-N-methylaminocarbonyl]cyclopropanecarboxylate having a melting point of 53 C.-56.5 C. NMR analysis of the product indicated the following: NMR (CDCl3): delta1.0-1.46 (m,7H), 3.35 (s,3H), 3.7-4.2 (m,2H), 7.0-7.47 (m,4H) ppm.

Reference： [1]Patent: US5292937,1994,A
[2]Patent: US5123951,1992,A

25
[ 693-98-1 ]
[ 13162-26-0 ]
[ 932-96-7 ]
2-(N-methyl4-chloroanilino)4-(2-methylimidazol-1-yl)-6-methyl-5-nitropyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15.6%	With acetic acid; In tetrahydrofuran; ethanol; hexane;	EXAMPLE 4 This example illustrates the synthesis of of 2-(N-methyl4-chloroanilino)4-(2-methylimidazol-1-yl)-6-methyl-5-nitropyrimidine (g). To a stirred, cold (-78 C.) solution of <strong>[13162-26-0]2,4-dichloro-6-methyl-5-nitropyrimidine</strong> (207.5 mg, 1.0 mmol, 1.0 eq) in THF (2.25 mL) and EtOH (2.25 mL) was added 2-methylimidazole (164 mg, 2.0 mmol, 2.0 eq) in a solution of EtOH (2.25 mL) dropwise. After 45 minutes, the dry ice bath was replaced with a water ice bath and stirring was continued for an additional 2.25 hours. 4-Chloro-N-methylaniline (0.485 mL, 4.0 mmol, 4.0 eq) was then added and the reaction solution was stirred for 2.7 hours. Solvent was removed by evaporation and the residue was diluted with dichloromethane, washed three times with 0.1M HCl, three times with saturated aqueous NaCl solution and dried over MgSO4. Solvent was removed from the organic phase and the residue was purified by silica gel chromatography (1:1 hexane/diethyl ether, 1% AcOH as eluant) to provide g (55.9 mg, 15.6%).

Reference： [1]Patent: US6200977,2001,B1

26
[ 121-39-1 ]
[ 932-96-7 ]
C₁₈H₂₀ClNO₃ [ No CAS ]
C₁₈H₂₀ClNO₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2464 - 2467

27
[ 932-96-7 ]
[ 25629-50-9 ]
[ 1197300-24-5 ]

Yield	Reaction Conditions	Operation in experiment
74%	With triethylamine In dichloromethane at 20℃; for 18h;

Reference： [1]Evans, Karen A.; Budzik, Brian W.; Ross, Sean A.; Wisnoski, David D.; Jin, Jian; Rivero, Ralph A.; Vimal, Mythily; Szewczyk, George R.; Jayawickreme, Channa; Moncol, David L.; Rimele, Thomas J.; Armour, Susan L.; Weaver, Susan P.; Griffin, Robert J.; Tadepalli, Sarva M.; Jeune, Michael R.; Shearer, Todd W.; Chen, Zibin B.; Chen, Lihong; Anderson, Donald L.; Becherer, J. David; De Los Frailes, Maite; Colilla, Francisco Javier [Journal of Medicinal Chemistry, 2009, vol. 52, # 24, p. 7962 - 7965]

28
[ 932-96-7 ]
[ 1122-91-4 ]
[ 1244043-41-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 20h;	(a) 4-r(4-Chlorophenyl)(methyl)aminolbenzaldehvde; Toluene (100 mL) and 4-chloro-Lambda/-methylaniline (4.58 mL, 37.8 mmol) were added to a mixture of Cs2CO3 (17.26 g, 53 mmol), Pd(OAc)2 (0.42 g, 1.9 mmol), BINAP (1.77 g, 2.8 mmol) and 4-bromobenzaldehyde (7 g, 37.8 mmol). The mixture was stirred at 85 0C for 20 h and filtered through Celite. The solids were washed with EtOAc. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 7.7 g (82%).
82%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 20h;	(b) 4-r(4-ChlorophenvO(methv?aminolbenzaldehvdeToluene (100 mL), followed by 4-chloro-Lambda/-methylaniline (4.58 mL, 37.8 mmol) were added to a mixture of Cs2CO3 (17.26 g, 53 mmol), Pd(OAc)2 (0.42 g, 1.9 mmol), BINAP (1.77 g, 2.8 mmol) and 4-bromobenzaldehyde (7 g, 37.8 mmol). The mixture was stirred at 85 0C for 20 h and filtered through Celite. The solids were washed with EtOAc. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 7.7 g (82%).

Reference： [1]Patent: WO2010/103279,2010,A1 .Location in patent: Page/Page column 71-72; 127
[2]Patent: WO2010/103297,2010,A2 .Location in patent: Page/Page column 71-72

29
[ 31181-90-5 ]
[ 932-96-7 ]
[ 1244043-46-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 16h;Product distribution / selectivity;	(a) 5-f(4-Chlorophenyl)methylaminolpyridine-2-carbaldehvde; The sub-title compound was prepared from 5-bromo-2-formylpyridine and 4-chloro-Lambda/-methylaniline in accordance with procedures described herein. Yield 2.5 g (96%). For instance, a mixture of 5-bromo-2-formylpyridine (e.g. 1.54 mmol), 4-chloro-Lambda/-methylaniline (e.g. 1.85 mmol), Pd(OAc)2 (e.g. 0.16 mmol), BINAP (e.g. 0.155 mmol), Cs2CO3 (e.g. 4.6 mmol) and toluene (e.g.10 mL) may be heated at 80 0C for 16 h. The mixture may be diluted with EtOAc and filtered through Celite. The combined filtrates may be concentrated and the residue purified by chromatography to give the sub-title compound.
58%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 15h;	(a) 5-((4-Chlorophenyl)(methyl)amino)picolinaldehvde; 4-Chloro-A/-methylaniline (1.6 mL, 12.9 mmol) in toluene (44 mL) was added to a mixture of Cs2C03 (4.9 g, 15.05 mmol), Pd(OAc)2 (0.121 g, 0.538 mmol), BINAP (0.502 g, 0.806 mmol) and 5-bromopicolinaldehyde (2.00 g, 10.75 mmol). The mixture was stirred at 85 C for 15 h and after cooling filtered through Celite. The solids were washed with EtOAc. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 1.537 g (58%).
58%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 15h;	<strong>[932-96-7]4-Chloro-N-methylaniline</strong> (1.6 mL, 12.9 mmol) in toluene (44 mL) was added to a mixture of Cs2CO3 (4.9 g, 15.05 mmol), Pd(OAc)2 (0.121 g, 0.538 mmol), BINAP (0.502 g, 0.806 mmol) and 5-bromopicolinaldehyde (2.00 g, 10.75 mmol). The mixture was stirred at 85 C. for 15 h and after cooling filtered through Celite. The solids were washed with EtOAc. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 1.537 g (58%).

	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 85℃; for 20h;Product distribution / selectivity;	(a) 5-r(4-Chlorophenv0methylamino]pyridine-2-carbaldehvde The sub-title compound was prepared from 5-bromo-2-formylpyridine and 4-chloro-Lambda/-methylaniline. Toluene (e.g.100 mL) and 4-chloro-Lambda/~methylaniline (e.g. 37.8 mmol) may be added to a mixture of Cs2CO3 (e.g. 53 mmol), Pd(OAc)2 (e.g. 1.9 mmol), BINAP (e.g. 2.8 mmol) and 5-bromo-2-formylpyridine (e.g. 37.8 mmol). The mixture may be stirred at 85 0C for 20 h and filtered through Celite. The solids may be washed with EtOAc. The combined filtrates may be concentrated and the residue purified by chromatography to give the sub-title compound.
528 mg	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 12h;	5-((4-chlorophenyl)(methyl)amino)pyridine-2-carbaldehyde was obtained from aBuchwald coupling of <strong>[932-96-7]4-chloro-N-methylaniline</strong> (0.42 mL, 3.5 mmol) and 5-bromopyridine-2-carbaldehyde (540 mg, 2.9 mmol) in toluene (10 mL) usingPd(OAc)2 (35 mg, 0.16 mmol), BINAP (137 mg, 0.22 mmol) and Cs2CO3 (1.3 g, 4.1mmol). The mixture was heated to 80C for 12 h. The intermediate was extracted toEtOAc, dried over Na2SO4 and purified by flash chromatography eluted with pentane/EtOAc (3:1). Yield: 528 mg of a light yellow oil,

Reference： [1]Patent: WO2010/103279,2010,A1 .Location in patent: Page/Page column 128
[2]Patent: WO2010/103278,2010,A1 .Location in patent: Page/Page column 81-82
[3]Patent: WO2011/110824,2011,A1 .Location in patent: Page/Page column 75-76
[4]Patent: US2013/35358,2013,A1 .Location in patent: Paragraph 0186
[5]Patent: WO2010/103297,2010,A2 .Location in patent: Page/Page column 93
[6]Journal of Pharmacology and Experimental Therapeutics,2015,vol. 355,p. 108 - 116

30
[ 1245703-33-6 ]
[ 932-96-7 ]
[ 1245703-34-7 ]

Yield	Reaction Conditions	Operation in experiment
75%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃; for 24h;	(c) 3-f4-r(4-ChlorophenvD(methyl)aminolbenzoyl)-5-nitrobenzoic acid methyl ester; A mixture of 3-(4-bromobenzoyl)-5-nitrobenzoic acid methyl ester (1.00 g, 2.75 mmol), 4-chloro-/V-methylaniline (0.47 g, 3.30 mmol), Pd(OAc)2 (31 mg, 0.14 mmol), BINAP (0.13 g, 0.21 mmol), Cs2CO3 (1.25 g, 3.84 mmol) and toluene (20 ml_) was heated at 100 0C for 24 h. The mixture was filtered through Celite and the solids washed with EtOAc. The combined filtrates were concentrated and purified by chromatography to give the sub-title compound. Yield: 874 mg (75%).

Reference： [1]Patent: WO2010/103279,2010,A1 .Location in patent: Page/Page column 67-68

31
[ 1129401-67-7 ]
[ 932-96-7 ]
[ 1129401-66-6 ]

Yield	Reaction Conditions	Operation in experiment
49%	With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 16h;	(b) 5-{4-r(4-ChlorophenvDamino1benzoyiy-2-fluorobenzoic acid methyl esterA mixture of 5-(4-bromobenzoyl)-2-fluorobenzoic acid methyl ester (0.52 g, 1.54 mmol), 4-chloro-Lambda/-methylaniline (0.26 g, 1.85 mmol), Pd(OAc)2 (35 mg, 0.16 mmol), BINAP (50 mg, 0.155 mmol), Cs2CO3 (1.5 g, 4.6 mmol) and toluene (10 mL) was heated at 80 0C for 16 h. The mixture was diluted with EtOAc and filtered through Celite. The combined filtrates were concentrated and the residue purified by chromatography to give the sub-title compound. Yield: 0.30 g (49%).

Reference： [1]Patent: WO2010/103297,2010,A2 .Location in patent: Page/Page column 67

32
[ 19836-78-3 ]
[ 932-96-7 ]
[ 1340503-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-methyl-2-oxo-1,3-oxazolidine; N-methyl(p-chloroaniline) at 160℃; for 10h; Neat (no solvent); Inert atmosphere; Stage #2: With water; potassium hydroxide at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Sakai, Norio; Watanabe, Akimasa; Ikeda, Reiko; Nakaike, Yumi; Konakahara, Takeo [Tetrahedron, 2010, vol. 66, # 46, p. 8837 - 8845]

33
[ 932-96-7 ]
[ 186407-74-9 ]
[ 1248590-74-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With RuPhos palladacycle; lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;

Reference： [1]Henderson, Jaclyn L.; Buchwald, Stephen L. [Organic Letters, 2010, vol. 12, # 20, p. 4442 - 4445]

34
[ 932-96-7 ]
[ 1071-36-9 ]
[ 68384-47-4 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4470 - 4474

35
[ 932-96-7 ]
[ 33046-50-3 ]
[ 1330539-97-3 ]

Yield	Reaction Conditions	Operation in experiment
54%	With hydrogenchloride In ethanol; water

Reference： [1]Location in patent: scheme or table Daly, Seth; Hayden, Kathryn; Malik, Indranil; Porch, Nikki; Tang, Hong; Rogelj, Snezna; Frolova, Liliya V.; Lepthien, Katrina; Kornienko, Alexander; Magedov, Igor V. [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 16, p. 4720 - 4723]

36
[ 932-96-7 ]
[ 616-83-1 ]
[ 1303573-31-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; dmap In dichloromethane at 0 - 20℃;	General procedure for the formation of nitrotoluene derivatives 7f-h,j-m General procedure: To a solution of the appropriate aniline in dry CH2Cl2 (10 mL for 3 mmol of aniline), pyridine (1.5 eq) and catalytic DMAP (15 mg) were added, then the resulting mixture was cooled to 0 °C. Subsequently, commercially available sulfonylchloride 6 (1.2 eq) in dry CH2Cl2 (10 mL for 3.6 mmol of benzenesulfonylchloride) was added dropwise and the reaction was kept under stirring at RT overnight. The reaction mixture was acidified with 1N aqueous HCl, extracted several times with CH2Cl2 and the combined organic phase was dried over anhydrous sodium sulphate. Evaporation under vacuum of the organic solvent afforded a crude product which was purified by column chromatography over silica gel, to yield the sulfonamidic derivative.

Reference： [1]Granchi, Carlotta; Roy, Sarabindu; Mottinelli, Marco; Nardini, Elisa; Campinoti, Fabio; Tuccinardi, Tiziano; Lanza, Mario; Betti, Laura; Giannaccini, Gino; Lucacchini, Antonio; Martinelli, Adriano; MacChia, Marco; Minutolo, Filippo [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 24, p. 7331 - 7336]

37
[ 1622-32-8 ]
[ 932-96-7 ]
[ 1404509-20-1 ]

Yield	Reaction Conditions	Operation in experiment
60.5%	With triethylamine; In dichloromethane; at 20℃; for 12h;	The weighed <strong>[932-96-7]4-chloro-N-methylaniline</strong> compound 16 (1.3 g, 9.5 mmol) was dissolved in an appropriate amount of dichloromethane solvent (about 20 mL). Then dichloroethanesulfonyl chloride (2.32 g, 14.25 mmol) was weighed into the reaction flask using a syringe. After cooling under ice-water bath conditions, triethylamine (2.9 g, 28.5 mmol) was added. The reaction was carried out for 12 hours at room temperature. After TLC thin layer chromatography was used to monitor the reaction, ethyl acetate was separated and the organic phase was washed with 1 M hydrochloric acid solution, then extracted and dried. Purification by column chromatography N-(4-Chlorophenyl)-N-methylvinylsulfonamide compound 32 (1.3 g, yield about 60.5%).

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 829 - 836
[2]Patent: CN108794519,2018,A .Location in patent: Paragraph 0093-0094; 0101-0103
[3]Organic and Biomolecular Chemistry,2012,vol. 10,p. 8692 - 8700

38
[ 124-38-9 ]
[ 932-96-7 ]
[ 698-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	With phenylsilane; C21H25N2(1+)*ZnBr2Cl(1-); potassium tert-butylate; at 100℃; under 750.075 Torr; for 20h;Autoclave;	General procedure: Under an argon atmosphere, a 3 mL vial was charged with 6b (5mol%), KOtBu (5 mol%) and CPME (2 mL). Substrate 8 (0.28 mmol,1 equiv.) and PhSiH3(3 equiv.) were added and the vial was sealed with a septum cap. The septum cap was pierced with a syringe needle and placed into a six-slot steal autoclave. The autoclave was sealed, purged twice with CO2 and heated at 100C (oil bath) under CO2 atmosphere (1 bar) for 20 h. After this time the reaction mixture was allowed to cool and the gas was carefully released. The reaction mixture was analyzed by gas chromatography (GC).

Reference： [1]Chemical Communications,2015,vol. 51,p. 11576 - 11579
[2]ACS Catalysis,2016,vol. 6,p. 1268 - 1273
[3]Green Chemistry,2017,vol. 19,p. 1726 - 1731
[4]Green Chemistry,2015,vol. 17,p. 4189 - 4193
[5]ChemSusChem,2018,vol. 11,p. 2296 - 2299
[6]Chemical Communications,2018,vol. 54,p. 11395 - 11398
[7]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5098 - 5104
[8]Angewandte Chemie - International Edition,2013,vol. 52,p. 9568 - 9571
    Angew. Chem.,2013,vol. 125,p. 9747 - 9750,4
[9]Green Chemistry,2020,vol. 22,p. 1134 - 1138
[10]Green Chemistry,2018,vol. 20,p. 4853 - 4858
[11]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2364 - 2369
[12]Chemical Science,2013,vol. 4,p. 2127 - 2131
[13]Angewandte Chemie - International Edition,2013,vol. 52,p. 9554 - 9557
    Angew. Chem.,2013,vol. 125,p. 9733 - 9736
[14]Angewandte Chemie - International Edition,2014,vol. 53,p. 12186 - 12190
    Angew. Chem.,2014,vol. 126,p. 12382 - 12386,5
[15]Journal of Molecular Catalysis A: Chemical,2016,vol. 423,p. 85 - 91
[16]Chemistry - A European Journal,2016,vol. 22,p. 16489 - 16493
[17]Angewandte Chemie - International Edition,2017,vol. 56,p. 7425 - 7429
    Angew. Chem.,2017,vol. 129,p. 7533 - 7537,5
[18]Green Chemistry,2018,vol. 20,p. 1564 - 1570
[19]Green Chemistry,2019,vol. 21,p. 567 - 577
[20]Angewandte Chemie - International Edition,2019,vol. 58,p. 9984 - 9988
    Angew. Chem.,2019,vol. 131,p. 10089 - 10093,5
[21]ACS Catalysis,2020,p. 3285 - 3296

39
[ 773873-77-1 ]
[ 932-96-7 ]
[ 1421349-52-1 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To the argon flushed solution of methyl indole-3-carboxylate (2a, 2.5 mmol) in CH2Cl2 (5 mL), a mixture of N-chlorosuccinimide (2.75 mmol) and N,N'-dimethylpiperazine (1.25 mmol) in CH2Cl2 (1 mL) was added dropwise at 0 C. The mixture was stirred at 0 C for 2 h, and a solution of trichloroacetic acid (0.63 mmol) and methyl 4-(methylamino)benzoate (3a, 5 mmol) in CH2Cl2 (2 mL) was then added. The reaction was allowed to warm to room temperature and further stirred for 3.5 h. The mixture was consecutively washed with saturated aqueous NaHCO3, 1 N HCl, brine, and water. The organic phase was dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (SiO2, Hexanes/EtOAc = 7/1) to give the white solids, mp: 193-194C; 1H NMR (600MHz, CDCl3) delta: 8.36 (s, 1H), 8.24 (d, J=1.9Hz, 1H), 7.31 (dd, J=8.5, 1.9Hz, 1H), 7.23-7.16 (m, 2H), 7.11 (d, J=8.5Hz, 1H), 6.79-6.75 (m, 2H), 3.82 (s, 3H), 3.41 (s, 3H); 13C NMR (150MHz, CDCl3) delta: 164.0, 147.9, 145.5, 130.4, 129.2, 128.2, 125.9(2C), 124.1, 117.5, 115.5, 112.0, 97.9, 51.1, 40.1. ESI-HRMS: m/z calcd. for C17H15BrClN2O2 [M+H]+ 393.0005. Found 393.0006.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 64,p. 498 - 511
[2]Medicinal Chemistry Research,2013,vol. 22,p. 4492 - 4504

40
[ 932-96-7 ]
[ 623-09-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 60℃; for 24h; Inert atmosphere;

Reference： [1]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]

41
[ 932-96-7 ]
[ 50803-29-7 ]
[ 1586822-27-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In ethyl acetate; at 0 - 20℃;	General procedure: Sulfonyl chloride derivative 1 or 2 (3.99mmol) was added gradually to a mixture of substituted amine (4.39mmol) and pyridine (2mL) in EtOAc with stirring at 0C. The reaction mixture was stirred at room temperature until the TLC indicated complete conversion of the sulfonyl chloride to the sulfonamide intermediate. The reaction mixture was dissolved in DCM and extracted (2×) with 10% NaOH. After the aqueous layer was acidified with 2N HCl, the precipitate was collected by filtration, washed with H2O, and dried in vacuo to give the desired products (5-22, 173, 174), which were carried forward without further purification.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 76,p. 414 - 426

42
[ 104-09-6 ]
[ 932-96-7 ]
[ 72681-26-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 90℃; for 15h;	Synthesis of 3-12; general procedure General procedure: An 50 mL vial was charged with magnetic stirring bar, arylacetaldehyde (1, 1.0 mmol), aromatic secondary amine (2,1.0 mmol), n-Bu4NI (0.2 mmol), TBHP 70% in water (4.0 mmol), followed by CH3CN/H2O (3/3 mL). After stirring at 90 °C for 15 h, the reaction mixture was quenched with a saturated solution of Na2SO3 (to remove excess TBHP) and extracted with EtOAc (20 mL × 2). The combined organic phase was dried over anhydrous Na2SO4 and then evaporated under reduced pressure. The isolated yield was obtained by flash chromatography column on silica gel (gradient eluent of ethylacetate in petroleum: 10-25%, v/v). Yield 55%; brown liquid; 1H NMR (400 MHz, CDCl3) δ 7.19-7.22 (m, 4H), 6.97-7.02 (m, 4H), 3.47 (s, 3H), 2.29 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 170.6, 143.7, 140.1, 132.6, 131.9, 129.3, 128.8, 128.6, 128.0, 38.4, 21.4; HRMS [M + 1]+: calcd C15H15ClNO 260.0842; found: 260.0848.

Reference： [1]Song, Ge; Sun, Gangchun; Tang, Yamin; Mai, Wenpeng [Journal of Chemical Research, 2013, vol. 37, # 10, p. 630 - 632]

43
[ 82278-73-7 ]
[ 932-96-7 ]
[ 1620084-37-8 ]

Yield	Reaction Conditions	Operation in experiment
5.6 g	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20℃;	Boc-L-3-BromoPhe (5g, 14.5 mmol) was dissolved in 50 mL of DMF and to it were added 4-chloro-N-methylaniline (2.1 mL, 17.4 mmol) and N, N-diisopropylethylamine (7.6 mL, 43.5 mmol). The reaction mixture was cooled to 0 C and to it was added HATU portion wise (6.6g, 17.4 mmol). The reaction mixture was allowed to stir at ambient temperature overnight and then was partitioned between ethyl acetate and water. The organic layer was separated and washed with 5 % aqueous LiCl, saturated aqueous NaHC03and brine. The mixture was then dried over MgS04, filtered and concentrated to afford crude product which was purified by silica gel chromatography eluting with ethyl acetate/hexanes to afford 5.6g of (S)-tert-butyl 3-(3- bromophenyl)-l-((4-chlorophenyl)(methyl)amino)-l-oxopropan-2-ylcarbamate as a white solid. MS (m/z): 469.1 [M+H]+; HPLC retention time 4.39 min (5-99% acetonitrile: water with 0.05% formic acid)

Reference： [1]Patent: WO2014/110296,2014,A1 .Location in patent: Paragraph 0214; 0215

44
[ 693803-49-5 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With trifluoroacetic acid; In dichloromethane; at 0℃; for 1.5h;	The weighed product (4-chlorophenyl)(methyl)carbamic acid tert-butyl ester compound 15 (2.3 g, 9.7 mmol) was dissolved in an appropriate amount of dichloromethane (about 10 mL). Trifluoroacetic acid (about 4 mL, 52.6 mmol) taken up in a syringe was added under ice water bath. After 1.5 hours of reaction at 0 C, the reaction was monitored by TLC thin layer chromatography to show that the reaction was completed. The extract was concentrated to dryness to give the product 4-chloro-N-methylaniline compound 16 (1.3 g, yield: about 99%). It was used directly in the next reaction without purification.

Reference： [1]Patent: CN108794519,2018,A .Location in patent: Paragraph 0093-0094; 0099-0100; 0103
[2]Organic Letters,2016,vol. 18,p. 6140 - 6143
[3]Angewandte Chemie - International Edition,2014,vol. 53,p. 7918 - 7922
Angew. Chem.,2014,vol. 53,p. 8052 - 8056,5
[4]Journal of Organic Chemistry,2015,vol. 80,p. 1258 - 1263

45
[ 18437-66-6 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 °C / Inert atmosphere; Schlenk technique 1.2: 20 °C / Inert atmosphere; Schlenk technique 2.1: trifluoroacetic acid / dichloromethane / 48 h / 40 °C / Inert atmosphere; Schlenk technique
	Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 0.02 h / 5 °C 2: hydrogenchloride / water / 120 °C
	Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 0 - 25 °C 2: trifluoroacetic acid / dichloromethane / 25 °C

Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.25 h / Inert atmosphere; Cooling with ice 1.2: 12 h / 20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C

Reference： [1]Doerfler, Jaika; Preuss, Till; Schischko, Alexandra; Schmidtmann, Marc; Doye, Sven [Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7918 - 7922][Angew. Chem., 2014, vol. 53, # 30, p. 8052 - 8056,5]
[2]Chen, Ming; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui [Journal of Organic Chemistry, 2015, vol. 80, # 2, p. 1258 - 1263]
[3]Youn, So Won; Kim, Yi Hyun [Organic Letters, 2016, vol. 18, # 23, p. 6140 - 6143]
[4]Current Patent Assignee: WUHAN UNIVERSITY - CN108794519, 2018, A

46
[ 932-96-7 ]
[ 1022-13-5 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 15352 - 15354

47
[ 64-18-6 ]
[ 932-96-7 ]
[ 698-69-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With dipotassium hydrogenphosphate; 18-crown-6 ether; In tetrahydrofuran; at 80℃; for 12h;Molecular sieve;	General procedure: In air, K2HPO4 (10 mol %, 4.35mg), PMHS (242 mul), amine (0.25 mmol), formic acid (4.6equiv ,43.3mul), 18-crown-6 (20mol %, 13.2mg) 4A MS(10mg) and 2 ml THF were added into a tube equipped with a water condenser. The reaction mixturewas stirred at 80C for 12 hours. The yields of isolated products were reported. The mixture was filtered through a silica gelcolumn with petroleum ether and ethyl acetate as the eluent. The resultant solution was concentrated and purified by silica gelcolumn chromatography to give the corresponding product.

Reference： [1]Organic Letters,2017,vol. 19,p. 1490 - 1493
[2]Chinese Chemical Letters,2019
[3]Chemical Communications,2014,vol. 50,p. 14033 - 14036
[4]Angewandte Chemie - International Edition,2018,vol. 57,p. 11673 - 11677
Angew. Chem.,2018,vol. 130,p. 11847 - 11851,5

48
[ 67-56-1 ]
[ 106-47-8 ]
[ 932-96-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With C19H37IrN4(2+)*2I(1-); potassium carbonate; at 120℃; for 17h;Inert atmosphere; Schlenk technique; Sealed tube;	General procedure: In a stainless reactor bomb, the respective aromatic amine (1.0mmol), 4c (0.50 mol%), K2CO3 (5.0 mol%), and MeOH (1.0 mL) were placed. Then, the reactor was sealed with a stainless stopper, and the mixture was stirred for 17 h at 120 C. After removing MeOH under reduced pressure, the products were isolated by silica gel column chromatography.
81%Chromat.	With platinum on carbon; sodium hydroxide; at 140℃; under 750.075 Torr; for 15h;Inert atmosphere; Autoclave;	General procedure: After the reduction under a flow of H2 at 300C for 0.5h, we carried out catalytic tests without exposing the catalyst to air as follows. Methanol (30mmol) was injected to the reduced catalyst inside the glass tube through a septum inlet, thus the catalyst was covered with a layer of methanol to restrict it from air exposure. After removal of the septum under air, amine (1mmol), solid NaOH (1mmol), n-dodecane (0.25mmol) and a magnetic stirrer bar were placed in the tube. The tube was inserted into a stainless-steel autoclave (28cm3) and purged with N2 gas. Finally, the resulting mixture was heated at 150C and stirred under 1barN2. For the model reaction of n-octylamine, the catalyst screening, optimization of reaction conditions, kinetic studies and control reactions, the conversion of n-octylamine and yields of products were determined by GC analyses, using n-dodecane as an internal standard by applying the GC sensitivity of the isolated or commercial products. For the substrate scope study, the products were isolated by column chromatography with silica gel 60 (spherical, 60-100mum, Kanto Chemical Co., Ltd.) using hexane/ethyl acetate or ethyl acetate/methanol as the eluting solvent. The yields of the isolated amine derivatives were determined and identified by 1H and 13C NMR and GC-MS methods.

Reference： [1]Dalton Transactions,2019,vol. 48,p. 5072 - 5082
[2]RSC Advances,2012,vol. 2,p. 8645 - 8652
[3]ACS Catalysis,2015,vol. 5,p. 4082 - 4088
[4]Synthesis,2018,vol. 50,p. 4617 - 4626
[5]Organic Letters,2017,vol. 19,p. 5790 - 5793
[6]Inorganic Chemistry,2020,vol. 59,p. 1835 - 1847
[7]Journal of Organic Chemistry,2020,vol. 85,p. 5815 - 5824
[8]Chemical Communications,2017,vol. 53,p. 1080 - 1083
[9]Chemical Communications,2019,vol. 55,p. 6213 - 6216
[10]Advanced Synthesis and Catalysis,2015,vol. 357,p. 3538 - 3548
[11]ACS Catalysis,2018,vol. 8,p. 6440 - 6445
[12]Journal of Catalysis,2017,vol. 347,p. 57 - 62
[13]ChemSusChem,2017,vol. 10,p. 2370 - 2374
[14]Organic Letters,2018,vol. 20,p. 3866 - 3870
[15]Journal of Catalysis,2019,vol. 371,p. 47 - 56

49
[ 53397-65-2 ]
[ 932-96-7 ]
C₃₀H₂₂Cl₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: N-methyl(p-chloroaniline) With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: sym-dibenzo-1,5-cyclooctadiene-3,7-diyne In tetrahydrofuran; hexane at -78 - 40℃; Inert atmosphere;

Reference： [1]Xu, Feng; Peng, Lifen; Shinohara, Kenta; Nishida, Takanori; Wakamatsu, Kan; Uejima, Motoyuki; Sato, Tohru; Tanaka, Kazuyoshi; Machida, Norihiko; Akashi, Haruo; Orita, Akihiro; Otera, Junzo [Organic Letters, 2015, vol. 17, # 12, p. 3014 - 3017]

50
[ 932-96-7 ]
[ 920-46-7 ]
N-methyl-p-chloromethacrylanilide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In tetrahydrofuran; at 0℃; for 2h;Inert atmosphere;	A solution of 1.02 mL (8.5 mmol) of <strong>[932-96-7]4-chloro-N-methylaniline</strong> and 0.90 mL (9.35mmol) of methacryloyl chloride in 85 mL of dry THF was stirred under Argon at 0 degrees and treated with 1.17 g (8.5 mmol) of potassium carbonate. The reaction mixture was stirred for 2 h, followed by addition of 2M HCl and extraction with ethylacetate. The aqueous layer was further extracted by ethyl acetate (2 x 50 mL) and the combined organic phases were dried over Na2SO4. The solvent was removed byrotary evaporation and the crude product was purified by column chromatography. Yield : 1.12 g, 63%; White solid, 1H NMR (500 MHz, DMSO): delta 7.44-7.40 (m, 2 H),7.31-7.28 (m, 2 H), 5.05-5.03 (m, 1 H), 4.84-4.82 (m, 1 H), 3.22 (s, 3 H), 1.74 (m, 3H); 13C NMR (125 MHz, DMSO): delta 170.5, 143.4, 140.3, 131.0, 129.1, 128.3, 118.5,37.0, 20.0; HRMS-(ESIpos) (m/z): M+ calcd for C11H12N1O1Cl1Na, 232.049961;found 232.049790.

Reference： [1]Chemical Communications,2018,vol. 54,p. 924 - 927
[2]Synlett,2015,vol. 26,p. 1973 - 1976
[3]Chemistry - An Asian Journal,2015,vol. 10,p. 1919 - 1925
[4]Organic Letters,2019,vol. 21,p. 4153 - 4158
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 10941 - 10945
Angew. Chem.,2019,vol. 131,p. 11057 - 11061,5
[6]Organic Letters,2020

51
[ 932-96-7 ]
[ 16019-31-1 ]
5-allyl-6-chloro-4-[(4-chlorophenyl)-N-methylamino]pyrimidine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 5360 - 5369

52
[ 932-96-7 ]
[ 16019-31-1 ]
4,8-dichloro-6,11-dimethyl-6,11-dihydro-5H-benzo[b]pyrimido-[5,4-f]azepine [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 5360 - 5369

53
[ 124-38-9 ]
[ 932-96-7 ]
[ 26772-93-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With phenylsilane; C56H50N2O2P2Zn(2+)*2Br(1-); In neat (no solvent); at 40℃; under 3750.38 Torr; for 6h;Autoclave;	General procedure: The reaction was carried out in a 10-mL stainless steel autoclave which was coupled with a magnetic stirrer. In a typical experiment for the N-formylation of amines with CO2 and hydrosilanes, N-methylaniline, the catalyst 3-PSZ-Br (or other catalysts when performing comparisons), and phenylsilane were added into the reactor. Subsequently, CO2 was charged into the reactor until the pressure reached 0.5 MPa and the reactor was then heated by an oil bath to 40 C while being stirred continuously. After the reaction, the autoclave was quickly cooled to 0 C and depressurized to atmospheric pressure [14]. The cycloaddition reactions with epoxides and CO2 were carried out in a similar fashion. Conversions and yields were determined using naphthalene or biphenyl as the internal standard and measured by a gas chromatograph (GC2010, Shimadzu Corporation, Japan) equipped with a capillary column (Rtx-5, 30 m × 0.32 mm × 0.25 mum) and a flame ionization detector (FID). The structure and the purity of the corresponding products were identified by 1H NMR, 13C NMR, and GC-MS analysis.

Reference： [1]Chemical Communications,2016,vol. 52,p. 7082 - 7085
[2]Chemical Communications,2018,vol. 54,p. 11395 - 11398
[3]Advanced Synthesis and Catalysis,2019,vol. 361,p. 5098 - 5104
[4]Journal of Materials Chemistry A,2018,vol. 6,p. 9172 - 9182
[5]Cuihua Xuebao/Chinese Journal of Catalysis,2017,vol. 38,p. 736 - 744
[6]Chemical Communications,2017,vol. 53,p. 8046 - 8049
[7]ChemSusChem,2017,vol. 10,p. 1224 - 1232
[8]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2364 - 2369
[9]ACS Catalysis,2015,vol. 5,p. 4989 - 4993
[10]Green Chemistry,2016,vol. 18,p. 3956 - 3961
[11]Chemistry - A European Journal,2016,vol. 22,p. 16489 - 16493
[12]Angewandte Chemie - International Edition,2017,vol. 56,p. 7425 - 7429
Angew. Chem.,2017,vol. 129,p. 7533 - 7537,5
[13]Green Chemistry,2018,vol. 20,p. 1564 - 1570
[14]Green Chemistry,2018,vol. 20,p. 4853 - 4858
[15]Green Chemistry,2019,vol. 21,p. 567 - 577
[16]Angewandte Chemie - International Edition,2019,vol. 58,p. 9984 - 9988
Angew. Chem.,2019,vol. 131,p. 10089 - 10093,5
[17]Green Chemistry,2020,vol. 22,p. 1134 - 1138

54
[ 75-15-0 ]
[ 773-82-0 ]
[ 932-96-7 ]
4-cyano-2,3,5,6-tetrafluorophenyl-N-(4-chlorophenyl)-N-methylcarbamodithioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: carbon disulfide; N-methyl(p-chloroaniline) With potassium hydroxide In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; Stage #2: Pentafluorobenzonitrile In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; regioselective reaction;	General procedure for the synthesis of 2,3,5,6-tetrafluorobenzonitrile-containing Dithiocarbamic Acid Esters (the synthesis of 4a as example) General procedure: Compound 1a (0.2 mmol, 39.5 mg), carbon disulfide 2 (0.4mmol, 30.4 mg), and K3PO4 (0.3 mmol, 63.5 mg) were weighted to a dried 10 mL schlenk flask under air. Then DMSO (2.0 mL) was added. The mixture was stirred at room temperature for approximately two hours. After substrate 1a completely disappeared (monitored by TLC), pentafluorobenzonitrile 3a (0.26 mmol, 50.4 mg) was added and the mixture continued stirring for another two hours. After the completion of the reaction (by TLC), water (5.0 mL) was added to the reaction media and extracted with CH2Cl2 (3×10.0 mL). The combined organic layers were washed with brine, and dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by flash column chromatography on silica gel to give the desired product 4a.

Reference： [1]Yin, Xuguang; Guo, Yamei; Liu, Cuibo; Wang, Zhifang; Zhang, Bin [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5135 - 5139]

55
[ 124-38-9 ]
[ 932-96-7 ]
N,N'-bis(4-chlorophenyl)-N,N'-dimethylmethanediamine [ No CAS ]

Reference： [1]ACS Catalysis,2015,vol. 5,p. 3983 - 3987
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 7425 - 7429
Angew. Chem.,2017,vol. 129,p. 7533 - 7537,5

56
[ 932-96-7 ]
[ 372-09-8 ]
[ 39217-12-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tert.-butylhydroperoxide; sodium acetate; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; water; at 80℃; for 12h;	TBAI in the reaction bottle (0.3mmol, 111 mg), compound1n (2mmol, 282 mg), compound2 (4mmol, 341 mg), NaOAc (4mmol, 164 mg), TBHP (0.60 ml), water (4.0 ml), tetrahydrofuran (4.0 ml). Then the system in the air 80 C heating under the conditions of about 12 hours, quenched with saturated sodium sulfite solution, extraction with ethyl acetate (40 ml × 3), silica gel adsorption, through the simple column chromatography can get product3n,the yield is 75%. The prepared test data mainly of the product are as follows, can be known through the analysis, the actual synthetic product is consistent with the theoretical analysis.

Reference： [1]Patent: CN105237435,2016,A .Location in patent: Paragraph 0074; 0075
[2]Chemistry - A European Journal,2015,vol. 21,p. 18333 - 18337

57
[ 117-34-0 ]
[ 932-96-7 ]
C₂₁H₁₈ClNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Inert atmosphere;	Typical procedure for the preparation of 1a General procedure: A solution of diphenylacetic acid (212 mg, 1.0 mmol), N-methylaniline (128 mg, 1.2mmol), DCC (247 mg, 1.2 mmol), and DMAP (24 mg, 0.2 mmol) in CH2Cl2 (1.5 mL) was stirred at room temperature for 15 h. After aqueous extractive workup and column chromatographic purification process (hexanes/Et2O,5:1) 1a was obtained as a white solid, 226 mg (75%). Other 2,2,N-triarylacetamides were prepared similarly from corresponding N-arylaminesand 2,2-diarylacetic acids. Diphenylacetic acid, bis(4-chlorophenyl)acetic acid and 9-fluorenecarboxylic acid were purchased from commercial sources, and other diarylacetic acids were prepared by Friedel-Crafts reaction of arenes and corresponding mandelic acid derivatives according to the reported methods.3,4

Reference： [1]Lim, Jin Woo; Kim, Ko Hoon; Moon, Hye Ran; Kim, Jae Nyoung [Tetrahedron Letters, 2016, vol. 57, # 7, p. 784 - 787]

58
[ 89539-54-8 ]
[ 932-96-7 ]
5-(benzyloxy)-2-(((4-chlorophenyl)(methyl)amino)methyl)-4H-pyran-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine; In N,N-dimethyl-formamide; at 60℃;Inert atmosphere;	[0537] 5-(Benzyloxy)-2-(((4-chlorophenyl)(methyl)amino)methyl)-4H-pyran-4-one (87): To a solution of 5-(benzyloxy)-2-(chloromethyl)-4H-pyran-4-one (250 mg, 0.997 mmol) and 4- chloro-N-methylaniline (282 mg, 1.995 mmol) in DMF (15 mL) was added triethylamine (0.306 mL, 2.194 mmol). The mixture was then heated to 60C and stirred overnight. The mixture was then evaporated to dryness under vacuum and purified by column chromatography to give compound 87 (201 mg, 79%). 1H NMR (400 MHz, CDC13): S 7.52 (s, 1H), 7.36 (dd, J = 12.7, 4.4 Hz, 5H), 7.16 (d, J = 9.0 Hz, 2H), 6.59 (d, J = 9.0 Hz, 2H), 6.26 (s, 1H), 5.05 (s, 2H), 4.25 (s, 2H), 3.01 (s, 3H). ESI-MS [M+H]+: 356.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 6444 - 6454
[2]Patent: WO2017/156194,2017,A1 .Location in patent: Paragraph 0537

59
[ 139-45-7 ]
[ 932-96-7 ]
4-chloro-N-methyl-N-propylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With tris(2,4-pentanedionato)ruthenium(III); hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 130℃; for 18h; Autoclave;

Reference： [1]Adam, Rosa; Cabrero-Antonino, Jose R.; Junge, Kathrin; Jackstell, Ralf; Beller, Matthias [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11049 - 11053][Angew. Chem., 2016, vol. 128, # 37, p. 11215 - 11219,5]

60
[ 538-23-8 ]
[ 932-96-7 ]
4-chloro-N-methyl-N-octylaniline [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 11049 - 11053
Angew. Chem.,2016,vol. 128,p. 11215 - 11219,5

61
[ 932-96-7 ]
[ 49647-20-3 ]
3-(4-acetylphenyl)-5-chloro-1-methyl-1,3-dihydro-2H-benzo[d]imidazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; silver carbonate In 1,2-dichloro-ethane at 120℃;

Reference： [1]Youn, So Won; Kim, Yi Hyun [Organic Letters, 2016, vol. 18, # 23, p. 6140 - 6143]

62
[ 932-96-7 ]
[ 205445-52-9 ]
C₂₁H₂₃ClF₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
108.7 mg	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 2h;	Intermediate 172 HATU (148 mg, 0.39 mmol) was added to a mixture of (S)-2-((tert- butoxycarbonyl)amino)-3-(3,5-difluorophenyl)propanoic acid (117 mg, 0.39 mmol) and 4-chloro-N-methylaniline (50 mg, 0.35 mmol) in DMF (2 mL) and DIPEA (0.18 mL, 1.1 mmol) and the reaction mixture was stirred at rt for 2 h. The reaction was filtered, and purified by preparative HPLC to afford the title compound (108.7 mg). LC-MS retention time = 2.37 min; m/z = 425.0 [M+H]+ (Column: Waters Acquity UPLC BEH CI 8, 2.1 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0-100% B over 3 minutes, then a 0.75-minute hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm). 3
108.7 mg	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 2h;	HATU (148 mg, 0.39 mmol) was added to a mixture of (S)-2-((tert- butoxycarbonyl)amino)-3-(3,5-difluorophenyl)propanoic acid (117 mg, 0.39 mmol) and 4-chloro-N-methylaniline (50 mg, 0.35 mmol) in DMF (2 mL) and DIPEA (0.18 mL, 1.1 mmol) and the reaction mixture was stirred at rt for 2 h. The reaction was filtered, and purified by preparative HPLC to afford the title compound (108.7 mg). LC-MS retention time = 2.37 min; m/z = 425.0 [M+H]+. (Column: Waters Acquity UPLC BEH CI 8, 2.1 x 50 mm, 1.7-mupiiota particles; Mobile Phase A: 5:95 acetonitrile:water with 10 mM (0666) ammonium acetate; Mobile Phase B: 95:5 acetonitrile:water with 10 mM ammonium acetate; Temperature: 50 C; Gradient: 0-100% B over 3 minutes, then a 0.75-minute hold at 100% B; Flow: 1.0 mL/min; Detection: UV at 220 nm).

Reference： [1]Patent: WO2016/172425,2016,A1 .Location in patent: Page/Page column 148
[2]Patent: WO2016/172424,2016,A1 .Location in patent: Page/Page column 98; 99

63
[ 932-96-7 ]
[ 952-10-3 ]
N-(4-chlorophenyl)-N-methyl-2,3-dioxo-1,2,3,4-tetrahydro-6-quinoxalinesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	In N,N-dimethyl-formamide at 20℃; for 12h; Inert atmosphere;

Reference： [1]Garzan, Atefeh; Willby, Melisa J.; Green, Keith D.; Gajadeera, Chathurada S.; Hou, Caixia; Tsodikov, Oleg V.; Posey, James E.; Garneau-Tsodikova, Sylvie [Journal of Medicinal Chemistry, 2016, vol. 59, # 23, p. 10619 - 10628]

64
[ 623-73-4 ]
[ 932-96-7 ]
ethyl 2-(N-(4-chlorophenyl)-N-methylamino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With [2-(4-hydroxymethyl)phenyl-4,4-(dimethyloxazole)Ru(CH3CN)4]PF6; In diethyl ether; water; at 20℃; for 1.6h;	General procedure: A solution of amine (0.3 mmol in 4.0 mL Et2O) was added to a solution of Ru(II)-hm-pheox 3 ( 0.0075 mmol, 2.5 mol%) in water ( 1.0 mL), then EDA (0.3 mmol, 1.0 equiv.) was injected and the biphasic reaction mixture was stirred at room temperature. At the end of reaction, the ether layer was removed by decantation and the water-soluble catalyst washed three times with ether (3 x 5.0 mL). The collected ether phase which contain the aminoester product was dried over anhydrous Na2SO4 and evaporated under reduced pressure. The products in most cases were pure enough and there is no need for further purification. The water phase which contain the catalyst was recycled several times. The 2-piperazinone product was purified by using column chromatography on silica gel (by using CH3OH only as eluent).
92%	With porous-polymer-supported ruthenium(II)-phenyloxazoline complex catalyst; In dichloromethane; at 20℃; for 0.25h;Inert atmosphere;	General procedure: A definite amount of polymer-supported ruthenium(II)-pheox complex cat. A was evacuated and backfilled with argon. The reaction flask was charged with (0.3 mmol) of amines dissolved in CH2Cl2 (3 mL) by injection through the side arm of the flask and the reaction flask was cooled in ice bath. Ethyldiazoacetate (0.035mL, 0.33 mmol) was slowly inserted and the reaction was stirred for 15 min at room temperature. The reaction product was isolated by centrifugation and the catalyst was separated by washing with acetonitrile and hexane respectively and dried under vacuum to be ready for the next use. The product in the filtrate was concentrated to afford the desired product in a pure form without further purification.

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4750 - 4754
[2]Asian Journal of Chemistry,2017,vol. 29,p. 349 - 352

65
[ 932-96-7 ]
[ 2617-79-0 ]

Yield	Reaction Conditions	Operation in experiment
48%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(II) acetate monohydrate In acetonitrile at 100℃; for 16h; Schlenk technique;
21%	With disodium hydrogenphosphate; potassium dihydrogenphosphate at 30℃; for 18h; Microbiological reaction; Green chemistry;

Reference： [1]Li, Dianjun; Wang, Shihaozhi; Yang, Jiale; Yang, Jinhui [European Journal of Organic Chemistry, 2021, vol. 2021, # 48, p. 6768 - 6772]
[2]Zheng, Daijun; Zhou, Xiaojian; Cui, Baodong; Han, Wenyong; Wan, Nanwei; Chen, Yongzheng [ChemCatChem, 2017, vol. 9, # 6, p. 937 - 940]

66
[ 1022-13-5 ]
[ 932-96-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2101 - 2106

67
[ 932-96-7 ]
[ 15249-31-7 ]
[ 2058-74-4 ]
[ 108726-52-9 ]
[ 26772-93-0 ]
[ 15950-17-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 3391 - 3400

68
[ 667-27-6 ]
[ 932-96-7 ]
[ 26772-93-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With water; In N,N-dimethyl-formamide; at 110℃; for 6h;Schlenk technique;	General procedure: A 25 mL oven-dried Schlenk tube was sequentially added N-methylaniline 1 or aniline 4 (0.2 mmol), Ethyl Bromodifluoroacetate 2a (81.2 mg, 0.4 mmol), DMF (1ml) and H2O (1 mL) was added under air. The reaction mixture was stirred for 6 h at 110. The solution was then diluted with ethyl acetate (20 mL), washed with brine (10 mL), extracted with ethyl acetate (3*5 mL), dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The crude reaction mixture was purified by column chromatography (silica gel, ethyl acetate/petroleum ether) yielded the desired product 3 or 5.
62%	With copper (I) acetate; caesium carbonate; XPhos; In N,N-dimethyl-formamide; at 110℃; for 12h;	28.2 mg (0.2 mmol) of N-methyl-4-chloroaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid N-(4-chlorophenyl)-N-methylformamide 21.0 mg, yield 62%.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1254 - 1258
[2]Patent: CN108774147,2018,A .Location in patent: Paragraph 0026
[3]Journal of Organic Chemistry,2018,vol. 83,p. 12815 - 12821

69
[ 932-96-7 ]
[ 145797-86-0 ]
2-((4-chlorophenyl)(methyl)amino)-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; potassium iodide In acetone at 80℃; for 2h; Microwave irradiation;	86B Step B. 2-((4-chlorophenyl)(methyl)amino)-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl-1-one 2-Bromo-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethanone (200 mg) and 4-chloro-N-methylaniline (111.4 mg, 1 equiv) were dissolved in 15 ml of acetone. Potassium carbonate (119 mg, 1.1 equiv), KI (144 mg 1.1 equiv) was then added. After reacting for 2 hours under microwave conditions at 80 ° C, the reaction solution was cooled, acetone was spun off, ethyl acetate (20 ml) was added for dilution, and then water was added thereto, and extraction was performed with ethyl acetate. The extracted ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, and then the solvent was removed by evaporation, using a petroleum ether/ethyl acetate (2:1) solvent. The product 2-((4-chlorophenyl)(methyl)amino)-1-(3,4-dihydroisoquinolin-2(1H)-yl)ethyl-1-one (200 mg, 81%).

Reference： [1]Current Patent Assignee: Shanghai Institute of Materia Medica (in: CAS); SHAOXING CONGLING PHARMACEUTICAL TECH; CHINESE ACADEMY OF SCIENCES - CN109020887, 2018, A Location in patent: Paragraph 0203; 0204; 0207-0208; 0209

70
[ 932-96-7 ]
[ 373-88-6 ]
4-chloro-N-methyl-N-(2,2,2-trifluoroethyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		2 mmol of trifluoroethylamine hydrochloride, 1 mL of water, was added to the reaction tube. 34 uL of acetic acid, 1 mL of dichloroethane, covered with a rubber stopper, and fixed on a stirrer. take 42 mg of sodium nitrite in a 1.5 mL sample tube, add 1 mL of water to the sample tube, and shake the sample. The tube is dissolved in sodium nitrite. Dissolving the dissolved sodium nitrite solution into the reaction tube with a syringe,Stir for half an hour at room temperature. dissolve the iron porphyrin of formula 4 with 1 mL of dichloromethane (R1 = SO3Na, R2 = R3 = H)(catalytic amount, 9/1000 of the molar amount of secondary amine),0.24 mmol of 4-chloro-N-methylaniline was taken in the sample tube. After half an hour, the mixed solution in the sample tube was added dropwise to the reaction tube, and stirred while stirring.The temperature was raised to 80 C for 12 hours. The reaction solution was cooled to room temperature and filtered to remove a portion.The impurities are concentrated and purified by column chromatography to obtain the target product. The column chromatography eluent is a mixed solvent of petroleum ether and acetone.The structure of 4-chloro-N-methyl-N-(2,2,2-trifluoroethyl)aniline is as follows:The compound was a pale yellow liquid with a yield of 70% and its nuclear magnetic data was as follows:

Reference： [1]Patent: CN108997145,2018,A .Location in patent: Paragraph 0103-0108

71
[ 17498-71-4 ]
[ 932-96-7 ]
[ 145838-86-4 ]
dimethyl 2-(2-((4-chlorophenyl)(methyl)amino)-3-methyl-2-phenylbutyl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With Succinimide In toluene at 70℃; Inert atmosphere;

Reference： [1]Zhang, Liang; Kong, Xiangjin; Liu, Shuya; Zhao, Zhiguo; Yu, Qun; Wang, Wei; Wang, Yao [Organic Letters, 2019, vol. 21, # 8, p. 2923 - 2926]

72
[ 201230-82-2 ]
[ 932-96-7 ]
[ 26772-93-0 ]

Yield	Reaction Conditions	Operation in experiment
89%	With phenylsilane; C19H37N2(1+)*Br(1-); In neat (no solvent); at 20℃; under 3750.38 Torr; for 12h;Autoclave;	General procedure: The formylation reaction was conducted in a stainless steel autoclave(25 ml inner volumes). In a typical reaction, the reactor wascharged with [DBUC12]Br (20.0 mg, 20 mol% relative to amine), Nmethylaniline(27 muL, 0.25 mmol) and phenylsilane (62 muL, 0.5 mmol)successively at room temperature. Then, CO2 was introduced into thereactor and the pressure was adjusted to 5 bar at room temperature for6 h. After the reaction was completed, the excess of CO2 was carefullyvented and then 1,3,5-trimethyoxybenzene (21.0 mg) was added as aninternal standard for 1H NMR yield determination. The residue waspurified by column chromatography with ethyl acetate-petroleumether as the eluent to afford the desired formylated product. Thecharacterization data

Reference： [1]Catalysis Today,2020

73
[ 774-05-0 ]
[ 932-96-7 ]
N-(4-chlorophenyl)-N-methyl-2-oxocycloheptanecarboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	for 24h; Reflux;	Preparation of Materials General procedure: A mixture of N-methylaniline (0.650 mL) and ethyl 2-oxocyclohexane-1-carboxylate (0.170 g) was heated under reflux for 24 h, then the crude products were separated by silica gel column chromatography eluting with EtOAc/hexane/acetone (2:7:1 v/v), giving N-methyl-2-oxo-N-phenylcyclohexane-1-carboxamide (1a) (0.126 g; 54% yield). The other N-alkyl-2-oxocycloalkane-1-carboxamides 1b-y were prepared according to a procedure similar to that already described.

Reference： [1]Katayama, Shintaro; Nishino, Hiroshi [Synthesis, 2019, vol. 51, # 17, p. 3277 - 3286]

74
[ 2985-33-3 ]
[ 932-96-7 ]
ethyl 3-((4-chlorophenyl)(methyl)amino)-2-methyl-3-oxopropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With 2-chloro-1-methyl-pyridinium iodide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere;
	With 2-chloro-1-methyl-pyridinium iodide; triethylamine In dichloromethane at 0 - 20℃; for 2.5h;

Reference： [1]Dobah, Farhaan; Mazodze, C. Munashe; Petersen, Wade F. [Organic Letters, 2021, vol. 23, # 14, p. 5466 - 5470]
[2]Zhao, Junyan; Song, Xun; Li, Dong; Zhao, Jinfeng; Qu, Jingping; Zhou, Yuhan [European Journal of Organic Chemistry, 2020, vol. 2020, # 40, p. 6392 - 6398]

75
[ 1198-30-7 ]
[ 932-96-7 ]
N-(4-chlorophenyl)-N-methylisoquinolin-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With 1,3-dicyano-5-fluoro-2,4,6-tris(diphenylamino)benzene In acetonitrile at 20℃; for 12h; Inert atmosphere; Irradiation;

Reference： [1]Zhou, Chao; Lei, Tao; Wei, Xiang-Zhu; Ye, Chen; Liu, Zan; Chen, Bin; Tung, Chen-Ho; Wu, Li-Zhu [Journal of the American Chemical Society, 2020, vol. 142, # 39, p. 16805 - 16813]

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