221044-05-9|1-(Pyrimidin-2-yl)-1H-indole| Ambeed

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Quality Control of [ 221044-05-9 ] Purity: 98% SDS Specification

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Product Details of [ 221044-05-9 ]

CAS No. :	221044-05-9
Formula :	C₁₂H₉N₃
M.W :	195.22
SMILES Code :	N1(C2=NC=CC=N2)C=CC3=C1C=CC=C3
MDL No. :	MFCD28556906
InChI Key :	CNAQMKUJWYJTRY-UHFFFAOYSA-N
Pubchem ID :	53381231

Safety of [ 221044-05-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 221044-05-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 221044-05-9 ]

[ 221044-05-9 ] Synthesis Path-Downstream 1~35

1
[ 1722-12-9 ]
[ 120-72-9 ]
[ 221044-05-9 ]

Yield	Reaction Conditions	Operation in experiment
96.4%		0.117g (1mmol) of indole (purchased from Beijing Bailingwei Technology Co., Ltd.) was dissolved in 2ml of anhydrous N,N-dimethylformamide (DMF) and added at 0C 0.044 g (1.1 mmol) sodium hydride (60% dispersed in mineral oil). The reaction was warmed to room temperature and stirred for 30 minutes. After 30 minutes, 0.137g (1.2mmol) of 2-chloropyrimidine (purchased from Beijing Bailingwei Technology Co., Ltd.) was added, and the reaction was heated to 130C for 5.0 hours. The reaction was followed by TLC. The indole point disappeared and the reaction was complete. 10ml of saturated aqueous sodium chloride solution was added, and the solid precipitated out. The solid was collected by suction filtration and dried to obtain 0.188 g of compound (III-1) with a yield of 96.4%.
91%		To a stirred of indole ( R1 ) (500 mg, 4.26 mmol) in DMF 50 mL), sodium hydride (0.9 g, 21.3 mmol) was added in several portions. The mixture was stirred under nitrogen at 0 C for 1 h. Then, 2- chloropyrimidine (1.2 g, 10.65 mmol) was added and stirred for 32 h at 120 C. After the reaction mixture was allowed to cool down to rt and poured into water (200 mL) and extracted with EtOAc (2 ×100 mL). The organic layer was dried over anhy- drous magnesium sulfate, and the solvent was removed to give brow oil, which was purified by column chromatography on sil- ica gel (EtOAc/ acetone, 4:1) to give R2 (756 mg, 91 %) as a colorless solid mp: 68 C, R f : 0.51 (EtOAc). UV max (CH 3 OH): 225, 285, 318 nm. IR (KBr): 2932, 2851, 1616, 1577, 1508, 1456, 1352, 909, 744, 609 cm -1 . H NMR (400 MHz, CDCl 3 ): 6.68 (d, J = 4.1 Hz, 1H), 6.93 (t, J = 4.7 Hz, 1H), 7.26 (t, J = 7.9 Hz, 1H) 7.33 (t, J = 8.6 Hz, 1H), 7.65 (d, J = 7.4 Hz, 1H), 8.29 (d, J = 3.6 Hz, 1H), 8.64 (d, J = 4.5 Hz, 2H), 8.81 (d, J = 9.3 Hz, 1H); 13 C NMR (100 MHz, CDCl 3 ): 106.83, 116.01, 116.21, 120.75, 122.04, 123.56, 125.73, 131.23ssssssssssssssssssssssssssssssssss4, 135.29, 157.67, 157.98. Found: C, 73.77; H, 4.72; N, 21.45. C 12 H 9 N 3 . Calculated, % C, 73.83; H, 4.65; N, 21.52.
85%		Indole (5mmol), DMF (10mL) and NaH (5mmol) were added to a 25mL reaction flask.The reaction mixture was stirred at 0C for 10 minutes, and then 2-chloropyrimidine (6 mmol) was added, and then the temperature was raised to room temperature to 130C for reaction. TLC detected until the reaction was complete.Perform post-treatment and purification: add water (20 mL) for quenching, extract with EA (20 mL×3), combine the organic phases, and wash with saturated NaCl (20 mL×2).After separation, dry with anhydrous magnesium sulfate, remove the organic solvent under reduced pressure, and separate and purify by silica gel column chromatography [V (petroleum ether): V (ethyl acetate) = 15:1] to obtain a pure product, a white solid , Yield: 85%.

74%	With sodium hydride; In N,N-dimethyl-formamide; at 20 - 120℃; for 18.03h;	1 H-indole(468 mg) in DMF (8 mL) was added 60% sodium hydride (176 mg)After stirring at room temperature for 20 minutes,2-Chloropyrimidine (504 mg) was added,And the mixture was stirred at 120 C. for 18 hours. After cooling the reaction solution to room temperature,Water was added and the obtained solid was collected by filtration,By washing with water1- (pyrimidin-2-yl) -1 H-indole578 mg (yield 74%) was obtained.
		General procedure: NaH(60% dispersion in mineral oil, 3.6 mmol) was added in portions at 0 C to a stirred solution of indole (3.0 mmol) in DMF (10 mL). After stirring for 30 min at 0C, chloropyrimidine(3.6 mmol) was added and the mixture was stirred at 130 C for 4-24 h. Then,the reaction mixture was cooled to ambient temperature, poured into H2O(20 mL) and extracted with EtOAc (25 mL×2). The combined organic phase was dried over Na2SO4. After filtration and evaporation ofthe solvents under reduced pressure, the crude product was purified by column chromatography on silica gel to afford the corresponding product.
		General procedure: NaH (60% dispersion in mineral oil, 300 mg, 7.5 mmol) was added in portions at 0 C to a stirred solution of indole (5.0 mmol) in DMF (8.0 mL). After stirring for 40 min at 0 C, 2-chloropyrimidine (687.18 g, 6.0 mmol) was added and the mixture was stirred at 130 C for 24 h. The reaction mixture was cooled to ambient temperature, quenched with H2O (90 mL) and then extracted with EtOAc (3×30 mL). The combined organic phase was dried over with anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude product was directly purified by column chromatography on silica gel (with EtOAc/petroleum) to get the corresponding product.1
		Synthesis of 1,1'-bis (pyrimidin-2-yl) -1H, 1'H-2,2'- two indoleIn the reaction vessel, was added indole (6mmol, 702.9mg), NaH (mass fraction of 60%, 10.8mmol, 432mg) for 30 minutes, DMF solvent, low temperature; then 2-chloropyrimidine (9.6mmol, 1099.488mg ), the mixture was reacted at 100 after 24 hours, cooled to room temperature, the solvent was removed by extraction, separation by column to give the compound 1- (pyrimidin-2-yl) lH-indole reactants.
		In the reaction container, adding indole (6mmol, 702.9 mg), NaH (mass fraction of 60%, 10 . 8mmol, 432 mg), DMF solvent, under the condition of low temperature reaction 30 minutes; then adding 2 - chloro pyrimidine (9.6mmol, 1099.5 mg), the mixture 130 C reaction under 24 hours, 24h through the TLC monitoring completion of the reaction, ethyl acetate after dilution for transfer to 250 ml separatory funnel, water washing three times, after cleaning DMF, collecting the organic phase with anhydrous sodium sulfate removal, decompression and steaming and removing the organic solvent to obtain the crude product, through the column chromatography (ethyl acetate: petroleum ether=1:99) to obtain compound 1 - (pyrimidinyl -2 - yl) - 1H - indole reactants. For thousand electronic balance accurate weighing 1 - (pyrimidinyl -2 - yl) - 1H - indole reactant (0.2mmol, 39 . 16 mg), transfer to the 25 ml pressure tube, to the reaction in the container adding PdCl2(CH3CN)2(25 µM %, 10.4 mg), Cs2CO3(0.04mmol,13mg), AgSbF6(0.02mmol,7mg), Al2O3(0.2mmol, 20.4 mg), dropping 2 ml 1, 4 - dioxane solvent in thick-walled pressure tube, and finally adding three ISO propyl silicon-based acetylene bromine (0.3mmol, 73 μl), the reaction of the reaction system is screwed plug sealing, heating to 120 C, oil bath under the stirring condition of reaction 15h. After the reaction, the reaction is cooled down to the room temperature, using a short silica gel column to remove some of the metal impurities in the preliminary purification, steaming and the solvent is removed under reduced pressure to get the crude product, the crude product is carried out column chromatography (eluant: ethyl acetate/petroleum ether=1:99), get the pure dry product, yield 69%.
		In a reaction vessel, indole (6 mmol, 702.9 mg), NaH (60% by mass, 10.8 mmol, 432 mg) and DMF solvent were added and the mixture was reacted at low temperature for 30 minutes; then, 2-chloropyrimidine (9.6 mmol, 1099.488 mg) was added and the mixture was reacted at 130 C for 24 hours. After cooling to room temperature, the solvent was removed by extraction and the mixture was separated by column to give 1- (pyrimidin-2-yl) -1H-indole. The 1- (pyrimidinyl-2-yl) -1H-indole reactant (0.3 mmol, 58.50 mg) was accurately weighed with a one-thousandth electronic balance and transferred to a thick-walled pressure resistant tube of a reaction vessel. To the reaction vessel was added PhI(OAc)2 (3eq, 289.5mg) was added dropwise 2mL of acetic acid / acetic anhydride = 7/3 mixed solvent, the reaction tube was screwed to the reaction system sealed, heated to 60 C, the reaction was stirred in an oil bath 36h. After the reaction was completed, the reaction solution was cooled to room temperature, a short silica gel column was used to remove some metal impurities for preliminary purification, the solvent was extracted and the solvent was removed, and the solvent was distilled off under reduced pressure to give a crude product. The crude product was subjected to column chromatography Deprotecting: ethyl acetate / petroleum ether = 15: 75) gave pure and dried product in 65% yield.
		Will be the substrate (1.0equiv),Anhydrous N,N-dimethylformamide is added to the reaction flask,After stirring at 0 C to cool to 0 C,Slowly add sodium hydride (60% by mass in mineral oil, 1.5 equiv) in batches.Then, the reaction solution was stirred at 0 C for 30 minutes,Add 2-chloropyrimidine (1.5equiv),The reaction solution was then transferred from 0 C to 140 C and stirred for 24 hours.After the reaction is completed, the heating is stopped, and after it is cooled to room temperature, an appropriate amount of water is added to quench the reaction, (sometimes due to the reaction The dosage should be large. After quenching the water, there will be a lot of solid impurities in the product. It needs to be filtered and washed with ethyl acetate several times to reduce the loss of the product. Then it is extracted with ethyl acetate until the water phase is almost no. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. Then filter and remove the solvent with a rotary evaporator, and use the silica gel for the crude product. Column chromatography (eluent: petroleum ether: ethyl acetate = 20:1) gave purified product A as a white solid.

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2
[ 221044-05-9 ]
[ 1310709-14-8 ]

References: [1]European Journal of Organic Chemistry,2021,vol. 2021,p. 4938 - 4942.
[2]Organic Letters,2011,vol. 13,p. 3332 - 3335.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 3172 - 3176.
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    Angewandte Chemie,2020,vol. 132,p. 23743 - 23749,7.

3
[ 273-53-0 ]
[ 221044-05-9 ]
[ 1402228-00-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate; Trimethylacetic acid; In 1,2-dichloro-benzene; at 140℃; for 24h;Schlenk technique; Sealed tube;	General procedure: 25 mL flame-dried Schlenk tube with a magnetic stir barwas charged with 1-(pyrimid-2-yl)-1H-indoles (1), benzoxazole(2a), catalyst, additive, and solvent. The tube was sealed under an O2 atmosphere. The reaction mixture was stirredvigorously and heated at 140 C for 24 h, and then cooled toambient temperature. The final reaction mixture was dilutedwith 10-20 mL of CH2Cl2, filtered through a Celite pad toremove insoluble salts, and then washed with 10-20 mL ofCH2Cl2. The combined CH2Cl2 extracts were concentratedin a vacuum evaporator and the crude product was purifiedby flash column chromatography on silica gel (petroleumether/ethyl acetate=3/1, v/v) to provide the cross-coupledproduct 3.

References: [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997.
[2]Science China Chemistry,2018,vol. 61,p. 200 - 205.

4
[ 10531-78-9 ]
[ 221044-05-9 ]
[ 1402228-01-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate; Trimethylacetic acid; In 1,2-dichloro-benzene; at 140℃; for 24h;Schlenk technique; Sealed tube;	General procedure: A 25 mL flame-dried Schlenk tube was charged with the1-(pyrimid-2-yl)-1H-indoles 1 (0.25 mmol), 1,3-azoles2 (0.75 mmol), [RhCp*Cl2]2 (3.9 mg, 2.5 mol%), AgSbF6(8.6 mg, 10 mol%), pivalic acid (PivOH,51 mg, 0.50 mmol), Ag2CO3 (6.9 mg, 10 mol%), and DCB(1.0 mL). The tube was sealed under an O2 atmosphere.The reaction mixture was stirred vigorously and heated at140 C for 24 h, and then cooled to ambient temperature.The final reaction mixture was diluted with 10-20 mL ofCH2Cl2, filtered through a Celite pad to remove insolublesalts, and then washed with 10-20 mL of CH2Cl2. Thecombined CH2Cl2 extracts were concentrated in a vacuumevaporator and the crude product was purified by flashcolumn chromatography on silica gel (petroleum ether/ethylacetate=3/1, v/v) to give the desired product 3 or 4.

References: [1]Science China Chemistry,2018,vol. 61,p. 200 - 205.
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997.

5
[ 221044-05-9 ]
C₁₂H₈⁽²⁾HN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With silver hexafluoroantimonate; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; water-d2; sodium acetate; 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one; In 1,2-dichloro-ethane; at 80℃; for 24h;Inert atmosphere;	<strong>[221044-05-9]1-(pyrimidin-2-yl)-1H-indole</strong> 1 (0.1 mmol, 1.0 equiv), TIP-EBX 2a (0.12 mmol, 1.2equiv), [Ru(cy-mene)Cl2]2 (5 mol %), AgSbF6 (0.02 mmol, 20 mol %), NaOAc (0.1mmol, 1.0 equiv) and 1,2-DCE (1 mL)/D2O (0.25 mL) were charged into a pressuretube under argon. The reaction mixture was stirred for 24 h at 80 oC under Aratmosphere, and then the mixture was cooled to room temperature. The solvent wasremoved under reduced pressure and the residue was purified by silica gelchromatography using EA/PE to afford the deuterated product.
	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; water-d2; at 80℃; for 12h;	<strong>[221044-05-9]1-(pyrimidin-2-yl)-1H-indole</strong> 1a (0.2 mmol, 1.0 equiv), but-3-en-2-ol 2a (0.4 mmol, 1.2 equiv), [Cp*RhCl2]2 (2.5 mol %), AgSbF6 (10 mol %), D2O (2.0 mL) were charged into Schlenk tube under air. The reaction mixture was stirred for 12 h at 80 C. After the reaction was complete, the mixture was extracted with CH2Cl2 three times. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to give the product.

References: [1]Organic Letters,2017,vol. 19,p. 3315 - 3318.
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[14]Chemical Communications,2020,vol. 56,p. 13169 - 13172.

6
[ 1006-68-4 ]
[ 221044-05-9 ]
[ 1402228-04-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate; Trimethylacetic acid; In 1,2-dichloro-benzene; at 140℃; for 24h;Schlenk technique; Sealed tube;	General procedure: A 25 mL flame-dried Schlenk tube was charged with the1-(pyrimid-2-yl)-1H-indoles 1 (0.25 mmol), 1,3-azoles2 (0.75 mmol), [RhCp*Cl2]2 (3.9 mg, 2.5 mol%), AgSbF6(8.6 mg, 10 mol%), pivalic acid (PivOH,51 mg, 0.50 mmol), Ag2CO3 (6.9 mg, 10 mol%), and DCB(1.0 mL). The tube was sealed under an O2 atmosphere.The reaction mixture was stirred vigorously and heated at140 C for 24 h, and then cooled to ambient temperature.The final reaction mixture was diluted with 10-20 mL ofCH2Cl2, filtered through a Celite pad to remove insolublesalts, and then washed with 10-20 mL of CH2Cl2. Thecombined CH2Cl2 extracts were concentrated in a vacuumevaporator and the crude product was purified by flashcolumn chromatography on silica gel (petroleum ether/ethylacetate=3/1, v/v) to give the desired product 3 or 4.

References: [1]Science China Chemistry,2018,vol. 61,p. 200 - 205.
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997.

7
[ 221044-05-9 ]
[ 17200-29-2 ]
[ 1402228-02-7 ]

Yield	Reaction Conditions	Operation in experiment
72%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; oxygen; silver carbonate; Trimethylacetic acid; In 1,2-dichloro-benzene; at 140℃; for 24h;Schlenk technique; Sealed tube;	General procedure: A 25 mL flame-dried Schlenk tube was charged with the1-(pyrimid-2-yl)-1H-indoles 1 (0.25 mmol), 1,3-azoles2 (0.75 mmol), [RhCp*Cl2]2 (3.9 mg, 2.5 mol%), AgSbF6(8.6 mg, 10 mol%), pivalic acid (PivOH,51 mg, 0.50 mmol), Ag2CO3 (6.9 mg, 10 mol%), and DCB(1.0 mL). The tube was sealed under an O2 atmosphere.The reaction mixture was stirred vigorously and heated at140 C for 24 h, and then cooled to ambient temperature.The final reaction mixture was diluted with 10-20 mL ofCH2Cl2, filtered through a Celite pad to remove insolublesalts, and then washed with 10-20 mL of CH2Cl2. Thecombined CH2Cl2 extracts were concentrated in a vacuumevaporator and the crude product was purified by flashcolumn chromatography on silica gel (petroleum ether/ethylacetate=3/1, v/v) to give the desired product 3 or 4.

References: [1]Science China Chemistry,2018,vol. 61,p. 200 - 205.
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 6993 - 6997.

8
[ 221044-05-9 ]
[ 36193-65-4 ]

References: [1]Organic Letters,2012,vol. 14,p. 4614 - 4617.
[2]Chemistry - A European Journal,2013,vol. 19,p. 16880 - 16886.
[3]Journal of Organic Chemistry,2015,vol. 80,p. 3695 - 3700.
[4]Angewandte Chemie - International Edition,2015,vol. 54,p. 3635 - 3638.
Angew. Chem.,2015,vol. 127.

9
[ 221044-05-9 ]
[ 4393-06-0 ]
[ 1446415-22-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With silver hexafluoroantimonate; at 20℃; for 24h;	To the polyethylene glycol-400 catalyst system obtained in Example 13 was added 1 mmol of N-pyrimidine indole and 2 mmol of 1-phenylpropen-1-ol, and the mixture was stirred at room temperature for 24 hours. The progress of the reaction was monitored by TLC. After completion, add ether to extract three times. The obtained polyethylene glycol-400 catalytic system was reused. It was put into the next experiment. The ether solution was combined and concentrated, and separated by column chromatography to obtain 285 mg of light yellow oily liquid with a yield of 87. %, the structural formula of the resulting product is as follows, the resulting polyethylene glycol-400 catalytic system is reused and put into the next experiment:
70%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In water; at 80℃; for 12h;Schlenk technique; Green chemistry;	General procedure: Heterocycles 1 (0.2mmol, 1.0 equiv), allylic alcohols 2 (0.4 mmol, 2.0 equiv), [Cp*RhCl2]2 (2.5mol %), AgSbF6 (0.02mmol, 10mol %) and H2O (2mL) were charged into a Schlenk tube under air. The reaction mixture was stirred for 12hat 80C. After the reaction was complete, the mixture was extracted with CH2Cl2 three times. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to give the pure product 3.

References: [1]Patent: CN111039927,2020,A .Location in patent: Paragraph 0054; 0117-0121.
[2]Chemical Communications,2013,vol. 49,p. 6489 - 6491.
[3]Tetrahedron,2018,vol. 74,p. 7364 - 7371.

10
[ 598-32-3 ]
[ 221044-05-9 ]
[ 1446415-19-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In water; at 80℃; for 12h;Schlenk technique; Green chemistry;	Heterocycles 1 (0.2mmol, 1.0 equiv), allylic alcohols 2 (0.4 mmol, 2.0 equiv), [Cp*RhCl2]2 (2.5mol %), AgSbF6 (0.02mmol, 10mol %) and H2O (2mL) were charged into a Schlenk tube under air. The reaction mixture was stirred for 12hat 80C. After the reaction was complete, the mixture was extracted with CH2Cl2 three times. The combined organic layer was dried with anhydrous Na2SO4 and evaporated in vacuum. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate as the eluent to give the pure product 3. 4.2. 4-(1-(Pyrimidin-2-yl)-1H-indol-2-yl)butan-2-one (3a) [9] Yield: 92%; 1H NMR (400MHz, CDCl3) δ 8.78 (d, J=4.8Hz, 2H), 8.29 (d, J=8.3Hz, 1H), 7.53-7.51 (m, 1H), 7.25-7.12 (m, 3H), 6.45 (s, 1H), 3.42 (t, J=7.8Hz, 2H), 2.90 (t, J=7.8Hz, 2H), 2.17 (s, 3H). 13C NMR (100MHz, CDCl3) δ 208.0, 158.2, 140.5, 136.9, 129.2, 122.8, 122.0, 119.8, 117.1, 114.1, 106.0, 43.5, 30.0, 23.8. HRMS (ESI+) calcd for C16H16N3O [M+H]+: 266.1288, found: 266.1286.
88%	With silver hexafluoroantimonate; at 20℃; for 24h;	Dissolve 1 mmol of <strong>[221044-05-9]N-pyrimidinylindole</strong> and 2 mmol of 3-buten-2-ol in a reactor containing 5 mL of polyethylene glycol-400,0.025mmol Dicyclopentadiene rhodium chloride dimer-based catalyst,0.10mmol silver hexafluoroantimonate as a co-catalyst,Stir at room temperature for 24 hours, monitor the progress of the reaction by TLC,After the reaction is complete, extract with ether three times,The obtained polyethylene glycol-400 catalytic system was reused and put into the next experiment,The ether solutions were combined and concentrated, and separated by column chromatography to obtain 234 mg of light yellow oily liquid with a yield of 88%,

References: [1]Chemical Communications,2013,vol. 49,p. 6489 - 6491.
[2]Tetrahedron,2018,vol. 74,p. 7364 - 7371.
[3]Patent: CN111039927,2020,A .Location in patent: Paragraph 0052-0056.
[4]Organic and Biomolecular Chemistry,2013,vol. 11,p. 8009 - 8013.

11
[ 221044-05-9 ]
[ 6843-66-9 ]
[ 1310708-93-0 ]

References: [1]Organic Letters,2014,vol. 16,p. 2614 - 2617.
[2]Organic Letters,2020,vol. 22,p. 2663 - 2668.

12
[ 221044-05-9 ]
[ 6843-66-9 ]
[ 948-65-2 ]

References: [1]Organic Letters,2014,vol. 16,p. 2614 - 2617.

13
[ 221044-05-9 ]
[ 5162-82-3 ]
C₁₉H₁₄ClN₃ [ No CAS ]

References: [1]ChemCatChem,2014,vol. 6,p. 3069 - 3074.

14
[ 221044-05-9 ]
[ 3218-36-8 ]
[1,1'-biphenyl]-4-yl(1-(pyrimidin-2-yl)-1H-indol-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values

References: [1]Synlett,2015,vol. 26,p. 771 - 778.
[2]ACS Catalysis,2017,vol. 7,p. 3818 - 3823.
[3]Journal of the American Chemical Society,2018,vol. 140,p. 586 - 589.

15
[ 221044-05-9 ]
[ 6630-33-7 ]
(2-bromophenyl)(1-(pyrimidin-2-yl)-1H-indol-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values
	With tert.-butylhydroperoxide; palladium diacetate; Trimethylacetic acid; In water; toluene; at 80℃; for 16h;Inert atmosphere;	General procedure: Step 1[1]: Pd(OAc)2 (0.2 mmol, 44.8 mg), Compound S1 (2.0 mmol), 2-bromobenzaldehyde (10.0mmol) PivOH (100 mg) and TBHP (4.0 mmol, 70% in water) were placed in a Schlenk flask.Then the flask was evacuated and backfilled with N2 for three times and then toluene (20 mL) wasadded. The reaction mixture was stirred at 80 for 16 h. After completion of reaction, thereaction was cooled down to room temperature and diluted with ethyl acetate. This mixture waspassed through a celite bed and washed with ethyl acetate. The combined organic layer thenwashed with saturated brine, dried and concentrated. The residue was purified by columnchromatography to give S2.

References: [1]Synlett,2015,vol. 26,p. 771 - 778.
[2]Synthesis,2022,vol. 54,p. 124 - 132.

16
[ 221044-05-9 ]
[ 66-77-3 ]
[ 1427669-85-9 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values

References: [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5899 - 5903.
[2]Synlett,2015,vol. 26,p. 771 - 778.
[3]Journal of the American Chemical Society,2018,vol. 140,p. 586 - 589.

17
[ 98-01-1 ]
[ 221044-05-9 ]
[ 1427669-91-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values

References: [1]ACS Catalysis,2017,vol. 7,p. 3818 - 3823.
[2]Synlett,2015,vol. 26,p. 771 - 778.
[3]RSC Advances,2015,vol. 5,p. 28292 - 28298.
[4]Journal of the American Chemical Society,2018,vol. 140,p. 586 - 589.

18
[ 924-44-7 ]
[ 221044-05-9 ]
ethyl 1-(pyrimidin-2-yl)-1H-indole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), glyoxylate (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values.

References: [1]Synlett,2015,vol. 26,p. 771 - 778.

19
[ 221044-05-9 ]
[ 123-11-5 ]
[ 1427669-83-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With tert.-butylhydroperoxide; palladium diacetate; In decane; ethyl acetate; at 125℃; for 24h;Inert atmosphere;	General procedure: To a 25-mL sealed tube were added indole (0.3 mmol), aldehyde (0.45 mmol), Pd(OAc)2 (6.72 mg,10 mmol%), TBHP (anhydrous, about 5M in decane) (4 equiv), EtOAc (2.0 mL). The tube wascapped and stirred under N2 at 125 C for 24 h. The reaction mixture was cooled to roomtemperature and diluted with CH2Cl2, filtered through a short pad of Celite, washed with brine andCH2Cl2 .The combined organic extracts were dried over Na2SO4, concentrated in vacuum, and theresulting residue was purified by silica gel column chromatography to afford the desired product.All compounds are characterized by 1H NMR, 13C NMR, LRMS/HRMS and their comparison toliterature values

References: [1]ACS Catalysis,2017,vol. 7,p. 3818 - 3823.
[2]Organic and Biomolecular Chemistry,2017,vol. 15,p. 5899 - 5903.
[3]Synlett,2015,vol. 26,p. 771 - 778.
[4]Journal of the American Chemical Society,2018,vol. 140,p. 586 - 589.

20
[ 221044-05-9 ]
[ 98-80-6 ]
[ 1310708-93-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Organic Letters,2017,vol. 19,p. 596 - 599.
[3]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

21
[ 221044-05-9 ]
[ 1679-18-1 ]
[ 1310708-95-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Organic Letters,2017,vol. 19,p. 596 - 599.
[3]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

22
[ 221044-05-9 ]
[ 5720-07-0 ]
[ 1310708-92-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

23
[ 221044-05-9 ]
[ 1765-93-1 ]
[ 1310708-94-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Organic Letters,2017,vol. 19,p. 596 - 599.
[3]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

24
[ 221044-05-9 ]
[ 128796-39-4 ]
[ 1608124-61-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Organic Letters,2017,vol. 19,p. 596 - 599.
[3]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

25
[ 221044-05-9 ]
[ 149104-90-5 ]
[ 1310709-06-8 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

26
[ 221044-05-9 ]
[ 99768-12-4 ]
4-acetylmethoxy-phenyl-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver trifluoroacetate; In methanol; at 60℃;Schlenk technique; Inert atmosphere;	General procedure: A mixture of N-pyrimidyl indoles 1 (0.20 mmol, 1.0 equiv.), arylboronicacids 2 (0.40 mmol, 2.0 equiv.),AgOOCF3 (0.80 mmol, 4.0 equiv.), and [RhCp*Cl2]2(0.002 mmol, 0.01 equiv.) were combined in MeOH (1.0 mL) in a dried Schlenk tubeunder a argon atmosphere. The resulting mixture was stirred at 60 C andmonitored by TLC. Uponcompletion or no further improvement of reaction, the reaction mixture wascooled to room temperature and added with Et3N (1 mL). Then themixture was filtered through a pad of silica gel eluting with 25 mL of CH2Cl2.The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to afford the desired products.

References: [1]Tetrahedron Letters,2015,vol. 56,p. 3754 - 3757.
[2]Chemistry - A European Journal,2015,vol. 21,p. 5380 - 5386.

27
[ 221044-05-9 ]
[ 536-74-3 ]
(E)-1-(pyrimidin-2-yl)-2-styryl-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; In acetic acid; at 20℃; for 12h;Schlenk technique; Inert atmosphere;	General procedure: To a dried Schlenk tube was equipped with a magnetic stirbar. [Cp*RhCl2]2 (0.005 mmol, 2.5 mol %, 3.1 mg), AgSbF6 (0.03 mmol, 15 mol %,10.3 mg), substrate 1 (0.2 mmol or 0.4 mmol), HOAc (1 ml), substrate 2 (0.24 mmolor 0.2 mmol) were added sequentially under argon. The tube was stirred at roomtemperature or 80 C for 12 h. After completion of the reaction, the mixture wasdiluted with EtOAc (10 mL), filtered through a short pad of silica gel and washedwith EtOAc (30 mL). The filtrate was pre-absorbed on silica gel and concentrated byrotary evaporation. The crude product was purified by flash silica gel (300-400 mesh)chromatography to afford the desired products product 3.

References: [1]ACS Catalysis,2017,vol. 7,p. 7296 - 7304.
[2]Chemical Communications,2016,vol. 52,p. 2709 - 2712.
[3]Synlett,2019,vol. 30,p. 932 - 938.
[4]Chemical Communications,2015,vol. 51,p. 7136 - 7139.

28
[ 221044-05-9 ]
[ 1424-22-2 ]
2-(cyclohex-1-en-1-yl)-1-(pyrimidin-2-yl)-1H-indole [ No CAS ]