Name: 52562-19-3|2-(Prop-1-en-2-yl)aniline|97%
Brand: Ambeed
SKU: A132304
Price: 19.0 USD
Availability: InStock
Rating: 99 (32 reviews)

1
[ 527-69-5 ]
[ 52562-19-3 ]
[ 119449-53-5 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3517 - 3520
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[3]Organic Letters,2018,vol. 20,p. 4052 - 4056
[4]Chemical Communications,2020,vol. 56,p. 2735 - 2738
[5]Green Chemistry,2021,vol. 23,p. 7982 - 7986

2
[ 110-62-3 ]
[ 52562-19-3 ]
[ 64935-38-2 ]
[ 115307-50-1 ]
[ 115307-51-2 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 4218 - 4222

3
[ 52562-19-3 ]
[ 79-03-8 ]
[ 119449-51-3 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3517 - 3520

4
[ 52562-19-3 ]
[ 555-16-8 ]
[ 115307-33-0 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 4218 - 4222
[2]Organic Letters,2022,vol. 24,p. 274 - 278

5
[ 52562-19-3 ]
[ 100-52-7 ]
(E)-1-phenyl-N-(2-(prop-1-en-2-yl)phenyl)methanimine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2021,vol. 363,p. 3775 - 3782
[2]Heterocycles,1986,vol. 24,p. 3385 - 3395

6
[ 52562-19-3 ]
[ 98-88-4 ]
[ 106012-41-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine; In dichloromethane; for 1h;Cooling with ice;	1: In a 100 mL three-necked flask, add methyl triphenylphosphonium bromide (5.36 g, 15 mmol) and dry THF 20 mL. Under the protection of argon, potassium tert-butoxide (1.68g, 15mmol) was added to the reaction flask in batches under ice bath, and after the addition, the reaction was carried out at room temperature for 30min. Then o-aminoacetophenone (1.21 g, 10 mmol) was added, and the reaction was carried out overnight. After the reaction was completed, saturated sodium bicarbonate was added, and the mixture was extracted with ethyl acetate. After the extract was concentrated, silica gel column chromatography was performed to obtain the corresponding o-propenylaniline (0.88 g, yield=74%). In a 100 mL single-neck flask, o-propenyl aniline (0.99 g, 7.4 mmol) and triethylamine (1.53 g, 11.1 mmol) were dissolved in 15 mL of dichloromethane. Under an ice bath, a dichloromethane solution of benzoyl chloride (1.0 mL, 8.9 mmol) was slowly added dropwise. The reaction was completed in about 1 hour. After silica gel column chromatography, the corresponding amide (3.89 g, yield=99%) was obtained. In a 100mL three-neck flask, add NaH (640mg, 60%wt, 16mmol), replace the gas in the flask with argon three times, add 15mL of dry THF, and add dropwise the THF solution with amide (700mg, 4mmol) dissolved in it. Reaction at 60C for 2h. Then, nitrile bromide was added to the reaction solution and moved to room temperature overnight. The reaction solution was suction filtered, and the filtrate was concentrated and subjected to silica gel column chromatography to obtain the target product 1 (448 mg). White solid, 56% yield

Reference： [1]Organic and biomolecular chemistry,2020,vol. 18,p. 1994 - 2001
[2]Patent: CN113024562,2021,A .Location in patent: Paragraph 0051; 0054-0055
[3]Journal of Chemical Research, Miniprint,1986,p. 1801 - 1833
[4]Tetrahedron Letters,1988,vol. 29,p. 3517 - 3520
[5]Synthesis,1993,p. 225 - 228
[6]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[7]Tetrahedron,2007,vol. 63,p. 8250 - 8254
[8]Organic Letters,2018,vol. 20,p. 4052 - 4056
[9]Chemical Communications,2020,vol. 56,p. 2735 - 2738
[10]Green Chemistry,2021,vol. 23,p. 7982 - 7986

7
[ 52562-19-3 ]
[ 874-60-2 ]
[ 148336-16-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[2]Synthesis,1993,p. 225 - 228
[3]Organic and biomolecular chemistry,2020,vol. 18,p. 1994 - 2001

8
[ 52562-19-3 ]
[ 122-01-0 ]
[ 148336-14-5 ]

Reference： [1]Synthesis,1993,p. 225 - 228
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[3]Journal of the American Chemical Society,2012,vol. 134,p. 12928 - 12931
[4]Organic and biomolecular chemistry,2020,vol. 18,p. 1994 - 2001
[5]Chemical Communications,2020,vol. 56,p. 2735 - 2738

9
[ 52562-19-3 ]
[ 100-07-2 ]
[ 148336-12-3 ]

Reference： [1]Synthesis,1993,p. 225 - 228
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[3]Journal of the American Chemical Society,2012,vol. 134,p. 12928 - 12931
[4]Organic and biomolecular chemistry,2020,vol. 18,p. 1994 - 2001
[5]Chemical Communications,2020,vol. 56,p. 2735 - 2738

10
[ 52562-19-3 ]
[ 122-04-3 ]
4-nitro-N-(2-(prop-1-en-2-yl)phenyl)benzamide [ No CAS ]

Reference： [1]Synthesis,1993,p. 225 - 228
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415

11
[ 52562-19-3 ]
[ 142-61-0 ]
[ 119449-52-4 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 3517 - 3520

12
[ 52562-19-3 ]
[ 98-59-9 ]
[ 106745-67-9 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; at 20℃; for 24h;	General procedure: The aniline (0.5 g, 3.75 mmol, 1 equiv) was dissolved in dry CH2Cl2 (7.5 mL, 0.5 M), and thesolution was treated with sulfonyl chloride (0.79 g, 4.13 mmol, 1.1 equiv) and pyridine (0.91mL, 11.3 mmol, 3 equiv). The mixture was stirred at room temperature for 24 h, diluted withH2O (25 mL) and extracted with CH2Cl2 (3 x 25 mL). The combined organic layers were washedwith 1M HCl, brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography of theresulting crude mixture on SiO2 (0-30% EtOAc in hexanes gradient) afforded the sulfonamidesin good yields. Substrate 1b was synthesized according to the above procedure using <strong>[52562-19-3]2-isopropenylaniline</strong> and 2-(trimethylsilyl)ethanesulfonyl chloride. Sulfonamide 1b was obtained

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 12771 - 12777
[2]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 3331 - 3334
[3]Tetrahedron,2004,vol. 60,p. 3017 - 3035
[4]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4783 - 4788
[5]Advanced Synthesis and Catalysis,2018,vol. 360,p. 1590 - 1594
[6]Tetrahedron Letters,2001,vol. 42,p. 8029 - 8033
[7]Tetrahedron,2007,vol. 63,p. 8250 - 8254
[8]Angewandte Chemie - International Edition,2014,vol. 53,p. 5170 - 5174
[9]Synlett,2015,vol. 26,p. 335 - 339
[10]Organic Letters,2020,vol. 22,p. 5473 - 5478

13
[ 52562-19-3 ]
[ 552-89-6 ]
[ 115307-34-1 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 4218 - 4222
[2]Organic Letters,2022,vol. 24,p. 274 - 278

14
[ 15781-74-5 ]
[ 52562-19-3 ]
[ 6780-49-0 ]
[ 101530-90-9 ]
[ 112794-56-6 ]

Reference： [1]Chemische Berichte,1988,vol. 121,p. 1143 - 1146

15
[ 52562-19-3 ]
[ 15781-71-2 ]
[ 6780-49-0 ]
[ 96807-23-7 ]
[ 112794-53-3 ]

Reference： [1]Chemische Berichte,1988,vol. 121,p. 1143 - 1146

16
[ 52562-19-3 ]
[ 6780-49-0 ]
[ 864131-95-3 ]
[ 112794-52-2 ]

Reference： [1]Chemische Berichte,1988,vol. 121,p. 1143 - 1146

17
[ 52562-19-3 ]
[ 75-36-5 ]
[ 72934-86-2 ]

Reference： [1]Journal of Chemical Research, Miniprint,1986,p. 1801 - 1833
[2]Organic Letters,2018,vol. 20,p. 1183 - 1186
[3]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[4]Journal of Organic Chemistry,2006,vol. 71,p. 7028 - 7034
[5]Tetrahedron,2007,vol. 63,p. 8250 - 8254
[6]Organic Letters,2018,vol. 20,p. 4052 - 4056
[7]Green Chemistry,2021,vol. 23,p. 7982 - 7986

18
[ 201230-82-2 ]
[ 52562-19-3 ]
[ 19155-24-9 ]

Reference： [1]Journal of the American Chemical Society,1996,vol. 118,p. 4264 - 4270
[2]Catalysis science and technology,2013,vol. 3,p. 3000 - 3006

19
[ 201230-82-2 ]
[ 52562-19-3 ]
[ 30696-28-7 ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1855 - 1861
[2]Journal of the American Chemical Society,1996,vol. 118,p. 4264 - 4270

20
[ 15833-00-8 ]
[ 52562-19-3 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 1003 - 1007
Angew. Chem.,2012,vol. 125,p. 1037 - 1041
[2]Tetrahedron,2007,vol. 63,p. 191 - 203
[3]Organic and Biomolecular Chemistry,2015,vol. 13,p. 11486 - 11491
[4]Synthetic Communications,1998,vol. 28,p. 2507 - 2516

21
[ 52562-19-3 ]
tetramethylammonium pentacarbonyl(1-oxyethylidene)-chromium⁽⁰⁾ [ No CAS ]
[ 1198-37-4 ]
[ 19343-79-4 ]
[ 19343-79-4 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5589 - 5591

22
pentacarbonyl(1-[N-(2-(2-propenyl)phenyl)amino]ethylidene)chromium [ No CAS ]
[ 1198-37-4 ]
[ 52562-19-3 ]

Reference： [1]Tetrahedron,2003,vol. 59,p. 8775 - 8791

23
[ 52562-19-3 ]
[ 3282-30-2 ]
N-[2-(1-methylethenyl)phenyl]-2,2-dimethylpropanamide [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,2006,vol. 79,p. 1580 - 1584
[2]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[3]Journal of the American Chemical Society,2012,vol. 134,p. 12928 - 12931
[4]Chemical Communications,2020,vol. 56,p. 2735 - 2738

24
[ 52562-19-3 ]
[ 98-74-8 ]
[ 918297-95-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; In dichloromethane; at 20℃; for 24h;	General procedure: The aniline (0.5 g, 3.75 mmol, 1 equiv) was dissolved in dry CH2Cl2 (7.5 mL, 0.5 M), and thesolution was treated with sulfonyl chloride (0.79 g, 4.13 mmol, 1.1 equiv) and pyridine (0.91mL, 11.3 mmol, 3 equiv). The mixture was stirred at room temperature for 24 h, diluted withH2O (25 mL) and extracted with CH2Cl2 (3 x 25 mL). The combined organic layers were washedwith 1M HCl, brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography of theresulting crude mixture on SiO2 (0-30% EtOAc in hexanes gradient) afforded the sulfonamidesin good yields. Substrate 1b was synthesized according to the above procedure using <strong>[52562-19-3]2-isopropenylaniline</strong> and 2-(trimethylsilyl)ethanesulfonyl chloride. Sulfonamide 1b was obtained

Reference： [1]Synlett,2015,vol. 26,p. 335 - 339
[2]Angewandte Chemie - International Edition,2018,vol. 57,p. 8255 - 8259
Angew. Chem.,2018,vol. 130,p. 8387 - 8391,5
[3]Tetrahedron,2007,vol. 63,p. 8250 - 8254
[4]Organic Letters,2020,vol. 22,p. 5473 - 5478

25
[ 52562-19-3 ]
[ 124-63-0 ]
[ 918297-94-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine; In dichloromethane; at 20℃; for 24h;	General procedure: The aniline (0.5 g, 3.75 mmol, 1 equiv) was dissolved in dry CH2Cl2 (7.5 mL, 0.5 M), and thesolution was treated with sulfonyl chloride (0.79 g, 4.13 mmol, 1.1 equiv) and pyridine (0.91mL, 11.3 mmol, 3 equiv). The mixture was stirred at room temperature for 24 h, diluted withH2O (25 mL) and extracted with CH2Cl2 (3 x 25 mL). The combined organic layers were washedwith 1M HCl, brine, dried over Na2SO4, and concentrated in vacuo. Flash chromatography of theresulting crude mixture on SiO2 (0-30% EtOAc in hexanes gradient) afforded the sulfonamidesin good yields. Substrate 1b was synthesized according to the above procedure using <strong>[52562-19-3]2-isopropenylaniline</strong> and 2-(trimethylsilyl)ethanesulfonyl chloride. Sulfonamide 1b was obtained

Reference： [1]Synlett,2015,vol. 26,p. 335 - 339
[2]Tetrahedron,2007,vol. 63,p. 8250 - 8254

26
[ 201230-82-2 ]
[ 52562-19-3 ]
[ 19343-78-3 ]

Reference： [1]Chemical Communications,2007,p. 2710 - 2711
[2]Synthesis,2010,p. 2893 - 2900

27
[ 201230-82-2 ]
[ 52562-19-3 ]
[ 19343-78-3 ]
[ 643-28-7 ]

Reference： [1]Chemical Communications,2007,p. 2710 - 2711

28
[ 52562-19-3 ]
[ 14722-38-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sodium nitrite; In hydrogenchloride;	EXAMPLE 1 4-(hydroxyiminomethyl)cinnoline hydrochloride (1) and 4-(hydroxyiminomethyl)cinnoline (2) A solution of 50.0 g of <strong>[52562-19-3]o-isopropenylaniline</strong> (Aldrich) in 440 ml of 2N hydrochloric acid was treated with 86 ml of 12N hydrochloric acid at 20 C. The resulting mixture was extracted with ether to remove a small amount of an insoluble oil. The aqueous phase was cooled to 0 C. and treated with 24.5 g of sodium nitrite, in portions, over 2 hours, at 0-5 C. The resulting mixture was stirred for 30 minutes at 0 C., warmed to room temperature, heated to 60 C., held at room temperature over a weekend, neutralized with sodium bicarbonate, made basic with 50% sodium hydroxide solution, and extracted with ether. The extract was washed with brine, dried (MgSO4), charcoaled, filtered and stripped of solvent. The residue was recrystallized from hexane to give 4-methylcinnoline (1A), as a solid, m.p.: 70-72 C.
	With sodium hydroxide; sodium nitrite; In hydrogenchloride;	EXAMPLE 27 Cinnoline-4-carboxamide (27) A solution of 50.0 g of <strong>[52562-19-3]o-isopropenylaniline</strong> (Aldtich) in 440 ml of 2 N hydrochloric acid was treated with 86 ml of 12 N hydrochloric acid at 20 C. The resulting mixture was extracted with ether to remove a small amount of an insoluble oil. The aqueous phase was cooled to 0 C. and treared with 24.5 g of sodium nitrite, in portions, over 2 hours, at 0-5 C. The resulting mixture was stirred for 30 minutes at 0 C., warmed to room temperature, heated to 60 C., and then held at room temperature over a weekend. It was neutralized with sodium bicarbonate, made basic with 50% sodium hydroxide solution, and extracted with ether. The extract was washed with brine, dried (MgSO4), charcoaled, filtered and stripped of solvent. The residue was recrystallized from hexane to give 4-methylcinnoline (27A), as a solid, m.p.: 70-72 C.

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 6318 - 6322
[2]Patent: US4564383,1986,A
[3]Patent: US4699651,1987,A

29
[ 19115-30-1 ]
[ 52562-19-3 ]
[ 141-97-9 ]
[ 1008132-57-7 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 9973 - 9981

30
[ 400743-82-0 ]
[ 20012-63-9 ]
[ 39643-31-7 ]
[ 728918-72-7 ]
C₈H₇F₄N [ No CAS ]
C₃₃H₂₉IN₅O₄Pol [ No CAS ]
[ 91646-45-6 ]
[ 4273-98-7 ]
[ 2264-92-8 ]
[ 1204-44-0 ]
[ 68817-71-0 ]
[ 369-36-8 ]
[ 37750-29-1 ]
[ 55751-54-7 ]
[ 18595-14-7 ]
[ 52562-19-3 ]
[ 62532-99-4 ]
[ 21627-58-7 ]
[ 73818-73-2 ]
[ 54705-91-8 ]
[ 26286-54-4 ]
[ 177171-13-0 ]
[ 99-55-8 ]
[ 23491-48-7 ]
[ 400750-84-7 ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₂H₃₇N₈O₄Pol [ No CAS ]
C₄₃H₄₃N₆O₄Pol [ No CAS ]
C₄₂H₃₉N₆O₄Pol [ No CAS ]
C₄₃H₃₇N₆O₄PolS [ No CAS ]
C₄₀H₃₆N₇O₆Pol [ No CAS ]
C₄₂H₃₉N₆O₆Pol [ No CAS ]
C₃₉H₃₃FN₇O₆Pol [ No CAS ]
C₄₄H₃₉N₆O₅Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₄Pol [ No CAS ]
C₄₃H₄₂N₇O₄Pol [ No CAS ]
C₄₆H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₈FN₆O₄Pol [ No CAS ]
C₄₅H₃₈ClN₆O₄Pol [ No CAS ]
C₄₁H₃₅F₄N₆O₄Pol [ No CAS ]
C₄₅H₃₉N₆O₆PolS [ No CAS ]
C₄₅H₃₈ClN₆O₄PolS [ No CAS ]
C₄₄H₄₄N₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₅Pol [ No CAS ]
C₄₅H₃₉ClN₇O₄Pol [ No CAS ]
C₄₇H₄₁N₆O₆Pol [ No CAS ]
C₄₅H₄₅N₈O₅Pol [ No CAS ]
C₄₄H₄₄N₉O₆Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In ISOPROPYLAMIDE; at 60℃;Combinatorial reaction / High throughput screening (HTS);	Step 2. Catalytic amination of the solid supported 8-iodo-l-methyl-4,5-dihydro- lH-pyrazolo [4,3-h] quinazoline-3-carboxamide; <n="82"/>Using a 4 niL Argonaut Trident synthesizer cassette, 200 mg (0.11 mmol) of the resin from step 1 above, were charged into separate vials. To each of the reactor vials flushed with argon, finely divided potassium carbonate (0.15 g, 1.1 mmol), palladium acetate [Pd(OAc)2] (2.5mg, 0.011 mmol, 10%), (HK)-BINAP (6.8 mg, 0.011 mmol, 10%) and the corresponding amine (0.22 mmol, 2 equivalents) in degassed (argon) dimethyacetamide (2 mL) were added. The resulting mixture was agitated at 600C for 10 hours on the Argonaut Trident Automated Library Synthesizer (ALS) station. The Trident ALS station was programmed to continuously mechanically agitate the resin at 6O0C while a nitrogen gas "sparge" was incorporated to re-suspend the scarcely soluble potassium carbonate. Nitrogen gas sparging was incorporated once per hour, for a 30 second duration, throughout the 16-hour heating cycle.The resin was drained from the synthesis cocktail and washed using the Argonaut Trident External Agitation Thermal Unit (EATU) synthesis station with DMA (3 x 2 mL, 5 min.). The above catalytic amination cycle was repeated a second time using the previously described procedure.Upon completion of the second amination cycle, the resin was drained from the synthesis cocktail and washed using the Argonaut Trident EATU synthesis station with DMF (1 x 2 mL, 5 min.), with water (1 x 2 mL, 5 min.), with DMF/water (1 : 1) (3 x 2 mL, 5 min.), with DMF (3 x 2 mL, 5 min.), with methanol (3 x 2 mL, 5 min.) and with DCM (3 x 2 mL, 5 min.).

Reference： [1]Patent: WO2008/74788,2008,A1 .Location in patent: Page/Page column 80-81

31
[ 640291-86-7 ]
[ 52562-19-3 ]
[ 1161929-10-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 8346 - 8347

32
[ 52562-19-3 ]
[ 107574-36-7 ]
[ 1161929-11-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 8346 - 8347

33
[ 33626-98-1 ]
[ 52562-19-3 ]
C₂₁H₁₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With tri-tert-butyl phosphine; palladium diacetate; caesium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; for 5h;Inert atmosphere; Reflux;	(Synthesis of Exemplary Compound (A-7)) (0457) Compound (A-7) in which D1 in Formula (I) is a compound represented by Formula (III) may be prepared by the following reaction scheme. 2-iso-propynylaniline (4.20 g, 31.5 mmol), palladium acetate (210 mg, 0.95 mmol), tri(t-butyl)phosphine (570 mg, 2.80 mmol), cesium carbonate (20.5 g, 62.9 mmol) and methyl 6-bromo-2-naphthoate (8.35 g, 31.5 mmol) were dissolved in 50 ml of xylene, and reacted by boiling under reflux for 5 hours under a nitrogen atmosphere to obtain Compound 17 in 78% yield. Compound 17 (7.80 g, 24.6 mmol) was added to a mixed solvent of 40 ml of acetic acid and 8 ml of hydrochloric acid, and followed by stirring at 60 C. for 30 minutes to obtain Compound 18 in 82% yield. Compound 18 (1.00 g, 3.15 mmol), palladium acetate (70.7 mg, 0.315 mmol), tri(t-butyl)phosphine (191 mg, 0.945 mmol), cesium carbonate (2.05 g, 6.30 mmol) and 1-bromo-4-tert-butylbenzene (671 mg, 3.15 mmol) were dissolved in 15 ml of xylene, and reacted by boiling under reflux for 7 hours under a nitrogen atmosphere to obtain Compound 19 in 95% yield. A 70% solution of sodium bis(2-methoxyethoxy)aluminum dihydride in toluene (5.37 ml, 18.6 mmol) was added to 13 ml of THF under a nitrogen atmosphere, and cooled to 0 C. N-methylpiperazine (2.01 g, 20.1 mmol) was added dropwise, and stirred for 30 minutes to adjust a reducing agent solution. The reducing agent solution was added dropwise to 20 ml of a solution of Compound 19 (1.35 g, 3.00 mmol) in THF at -40 C. under a nitrogen atmosphere. The reaction solution was stirred at -20 C. for 4 hours, and the reaction was then stopped with diluted hydrochloric acid to obtain Compound 20 in 81% yield. Compound 20 (700 mg, 1.67 mmol) and benzindandione (361 mg, 1.84 mmol) were added to 9 ml of an acetic acid solvent under a nitrogen atmosphere, and refluxed for 3 hours. After allowing to cool, suction filtration was performed, and recrystallization was performed with N,N-dimethylacetamide. Suction filtration was performed to obtain Compound (A-7) in 51% yield. The compound was identified by 1H-NMR. (0460) 1H-NMR (400 M Hz, in CDCl3): δ (ppm)=1.45 (s, 9H), 2.31 (s, 6H), 6.09 (d, J=8.6 Hz, 1H), 6.53 (d, J=8.7 Hz, 1H), 6.89-6.98 (m, 2H), 7.22 (d, J=8.7 Hz, 2H), 7.48-7.56 (m, 2H), 7.63-7.72 (m, 4H), 8.04-8.12 (m, 3H), 8.47-8.57 (m, 3H), 8.69-8.73 (m, 1H), 8.79 (s, 1H). m.p.=335 C., λmax=568 nm (in CHCl3) (ε=53000 mol-1·l·cm-1)
	With caesium carbonate;palladium diacetate; triphenylphosphine; In xylene; for 4h;Reflux;	(Example 12) <Synthesis of Compound (12)> [Show Image]<Synthesis of Compound 12a"> To 50 ml of dehydrated xylene, 4.2 g of <strong>[52562-19-3]2-isopropenylaniline</strong> (produced by Aldrich Chemical Co. Inc.), 8.4 g of methyl 6-bromo-2-naphthoate (produced by Wako Pure Chemical Industries, Ltd.), 210 mg of palladium acetate, 740 mg of triphenylphosphine and 20.5 g of cesium carbonate were added, followed by refluxing for 4 hours. The reaction mixture was suction-filtered and after distilling off the solvent by an evaporator, the residue was purified on a silica gel column (developing solvent: toluene). The solvent was distilled off to obtain 7.8 g of Compound (12a").

Reference： [1]Patent: US9349965,2016,B2 .Location in patent: Page/Page column 123-125
[2]Patent: EP2292586,2011,A2 .Location in patent: Page/Page column 46

34
[ 52562-19-3 ]
[ 1361944-15-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1428 - 1431

35
[ 5271-67-0 ]
[ 52562-19-3 ]
[ 1392323-21-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 8411 - 8415
[2]Journal of the American Chemical Society,2012,vol. 134,p. 12928 - 12931
[3]Organic Letters,2018,vol. 20,p. 4052 - 4056
[4]Chemical Communications,2020,vol. 56,p. 2735 - 2738
[5]Green Chemistry,2021,vol. 23,p. 7982 - 7986

36
[ 52562-19-3 ]
[ 98-80-6 ]
[ 112817-88-6 ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: PhB(OH)2 (0.15 g, 1.2 mmol, 1.2 equiv), Cu(OAc)2 (0.036 g, 0.2 mmol, 0.2 equiv) and myristicacid (0.091 g, 0.4 mmol, 0.4 equiv) were dissolved in toluene (2 mL, 0.5M). The reaction wasstirred, 2,6-lutidine (0.12 mL, 1 mmol, 1 equiv) and <strong>[52562-19-3]2-isopropenylaniline</strong> (0.14 mL, 1 mmol, 1equiv) were added. The reaction was stirred at room temperature exposed to air for 24 h.TEMPO (0.031 g, 0.2 mmol, 0.2 equiv) and toluene (8 mL, 0.1M overall) were then added. Theflask was purged with O2, put under an O2 atmosphere using an O2 balloon and stirred for 24 h at120 oC. Filtration of the cooled reaction mixture through a pad of silica gel with ethyl acetate(100 mL), and subsequent evaporation of the solvent in vacuo afforded crude mixtures. Flashchromatography of the resulting crude mixture on silica gel (0-5% diethyl ether in hexanesgradient) afforded the known indole 2g (0.11 g, 53% yield) as a yellow liquid.

Reference： [1]Synlett,2015,vol. 26,p. 335 - 339
[2]Chemistry - A European Journal,2013,vol. 19,p. 12771 - 12777

37
[ 27200-84-6 ]
[ 551-93-9 ]
[ 52562-19-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In tetrahydrofuran; at 20℃;Inert atmosphere;	General procedure: To a solution of Ph3PMeBr(1.5 equiv) in dry THF was added t-BuOK (1.5 equiv) in portions under N2atmosphere at room temperature. After the mixture was stirred at room temperaturefor 0.5 h, a solution of SI-5 (1equiv)in THF was added dropwise. The reaction mixture was then stirred at room temperatureunder N2 overnight. The reaction mixture was quenched with H2Oand extracted twice with EtOAc. The combined organic layers were washed withsaturated NaHCO3and brine, dried over MgSO4, filtered andconcentrated, and the residue was purified by column chromatography on silicagel to obtain SI-6

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 3229 - 3231
[2]Journal of Organic Chemistry,2019,vol. 84,p. 10843 - 10851

38
[ 52562-19-3 ]
[ 106018-85-3 ]
N-(2-(prop-1-en-2-yl)phenyl)-2-(trimethylsilyl)ethane-1-sulfonamide [ No CAS ]