[ CAS No. 850623-36-8 ] {[proInfo.proName]}

Name: 850623-36-8|Potassium (4-cyanophenyl)trifluoroborate|97%
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SKU: A330304
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Quality Control of [ 850623-36-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 850623-36-8 ]

SDS Specification

Alternatived Products of [ 850623-36-8 ]

Product Details of [ 850623-36-8 ]

CAS No. :	850623-36-8	MDL No. :	MFCD04115736
Formula :	C₇H₄BF₃KN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JEQAKQWNUUSKHI-UHFFFAOYSA-N
M.W :	209.02	Pubchem ID :	23716872
Synonyms :

Calculated chemistry of [ 850623-36-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.87
TPSA :	23.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.16
Log Po/w (WLOGP) :	2.87
Log Po/w (MLOGP) :	1.94
Log Po/w (SILICOS-IT) :	1.25
Consensus Log Po/w :	1.84

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.4
Solubility :	0.0828 mg/ml ; 0.000396 mol/l
Class :	Soluble
Log S (Ali) :	-3.33
Solubility :	0.0978 mg/ml ; 0.000468 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.36
Solubility :	0.0914 mg/ml ; 0.000438 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.02

Safety of [ 850623-36-8 ]

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

Application In Synthesis of [ 850623-36-8 ]

* 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 [ 850623-36-8 ]
Downstream synthetic route of [ 850623-36-8 ]

[ 850623-36-8 ] Synthesis Path-Upstream 1~1

1
[ 850623-36-8 ]
[ 126747-14-6 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7364 - 7369

[ 850623-36-8 ] Synthesis Path-Downstream 1~50

1
[ 850623-36-8 ]
[ 16650-63-8 ]
[ 1033204-03-3 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 3204 - 3207

2
[ 4857-06-1 ]
[ 850623-36-8 ]
[ 4110-15-0 ]

Reference： [1]Tetrahedron Letters,2008,vol. 49,p. 6667 - 6669

3
[ 850623-36-8 ]
[ 126747-14-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 7364 - 7369

4
[ 850623-36-8 ]
[ 38262-42-9 ]
[ 27331-37-9 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 4022 - 4025

5
[ 850623-36-8 ]
[ 475983-77-8 ]
[ 1260684-53-4 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 6393 - 6403

6
[ 161664-51-3 ]
[ 850623-36-8 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 6393 - 6403

7
[ 623-03-0 ]
[ 1279123-63-5 ]
[ 13675-18-8 ]
[ 850623-36-8 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673
[2]Journal of the American Chemical Society,2010,vol. 132,p. 17701 - 17703

8
[ 850623-36-8 ]
[ 767-00-0 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 623 - 630

9
[ 623-03-0 ]
[ 850623-36-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 6427 - 6439
[2]Journal of the American Chemical Society,2010,vol. 132,p. 17701 - 17703
[3]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673

10
[ 850623-36-8 ]
[ 591-87-7 ]
(E)-3-(4-cyanophenyl)-2-propen-1-ol acetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2012,vol. 354,p. 1069 - 1076

11
[ 850623-36-8 ]
[ 1381781-06-1 ]
4-{2-[4-(3,7-dimethyl-octa-2,6-dienyl)-3,5-bis-methoxymethoxy-phenyl]-vinyl}-benzonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4122 - 4126

12
[ 126747-14-6 ]
[ 850623-36-8 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 9385 - 9388
[2]Journal of the American Chemical Society,2012,vol. 134,p. 11667 - 11673
[3]Journal of Organic Chemistry,2012,vol. 77,p. 6384 - 6393
[4]Journal of Organic Chemistry,2013,vol. 78,p. 6427 - 6439

13
[ 850623-36-8 ]
[ 1388707-61-6 ]
[ 1350898-35-9 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6384 - 6393

14
[ 850623-36-8 ]
[ 171617-28-0 ]
[ 1350898-41-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 6384 - 6393

15
[ 850623-36-8 ]
[ 1364678-39-6 ]

Reference： [1]Patent: US2013/65876,2013,A1
[2]Patent: WO2013/37703,2013,A1
[3]Patent: WO2020/21097,2020,A1

16
[ 850623-36-8 ]
[ 1427064-47-8 ]

Reference： [1]Patent: US2013/65876,2013,A1
[2]Patent: WO2013/37703,2013,A1

17
[ 850623-36-8 ]
[ 1211589-51-3 ]
[ 1427064-93-4 ]

Yield	Reaction Conditions	Operation in experiment
898 mg	With di-(1-adamantyl)-n-butylphosphine; palladium diacetate; caesium carbonate; In water; toluene; at 120℃; for 5h;Inert atmosphere;	a) 5-(4-Cyano-phenyl)-6-(2,2,2-trifluoro-ethoxy)-nicotinic acid methyl ester In a 50 mL 4-necked flask, methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinate (1 g, 3.18 mmol, Eq: 1.00, CAN 121 1589-51-3) and cesium carbonate (3.1 1 g, 9.55 mmol, Eq: 3) were combined with toluene (25 ml) and water (2.8 ml) to give a colorless solution. The reaction mixture was 3x degassed and purged with argon; then palladium (II) acetate (14.3 mg, 63.7 ?????, Eq: 0.02), <strong>[850623-36-8]potassium (4-cyanophenyl)trifluoroborate</strong> (732 mg, 3.5 mmol, Eq: 1.1, CAN 850623- 36-8) and butyldi-l-adamantylphosphine (68.5 mg, 191 ?????, Eq: 0.06) were successively added. The degassing - purging cycle was repeated after each addition. The reaction mixture was then heated to 120 C for 5 hours. After cooling, the reaction mixture was poured into 50mL H20 and extracted with AcOEt (2x50 mL). The organic layers were washed with H20/NaCl solution, combined, dried over Na2S04 and concentrated in vacuo. Purification by flash chromatography (silica gel, 50 g, 50% to 100 % CH2C12 in heptane) yielded finally 898 mg of the title compound as white foam; MS (EI) 337.2 (M+H)+.
898 mg	With palladium diacetate; caesium carbonate; catacxium A; In water; toluene; at 120℃; for 5h;Inert atmosphere;	[0388] In a 50 mL 4-necked flask, methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinate (1 g, 3.18 mmol, Eq: 1.00, CAN 1211589-51-3) and cesium carbonate (3.11 g, 9.55 mmol, Eq: 3) were combined with toluene (25 ml) and water (2.8 ml) to give a colorless solution. The reaction mixture was 3× degassed and purged with argon; then palladium(II) acetate (14.3 mg, 63.7 mumol, Eq: 0.02), <strong>[850623-36-8]potassium (4-cyanophenyl)trifluoroborate</strong> (732 mg, 3.5 mmol, Eq: 1.1, CAN 850623-36-8) and butyldi-1-adamantylphosphine (68.5 mg, 191 mumol, Eq: 0.06) were successively added. The degassing-purging cycle was repeated after each addition. The reaction mixture was then heated to 120 C. for 5 hours. After cooling, the reaction mixture was poured into 50 mL H2O and extracted with AcOEt (2×50 mL). The organic layers were washed with H2O/NaCl solution, combined, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography (silica gel, 50 g, 50% to 100% CH2Cl2 in heptane) yielded finally 898 mg of the title compound as white foam; MS (EI) 337.2 (M+H)+
898 mg	With palladium diacetate; caesium carbonate; catacxium A; In water; toluene; at 120℃; for 5h;	In a 50 mL 4-necked flask, methyl 5-bromo-6-(2,2,2-trifluoroethoxy)nicotinate (1 g, 3.18 mmol, Eq: 1.00, CAS Reg. No. 1211589-51-3) and cesium carbonate (3.11 g, 9.55 mmol, Eq: 3) were combined with toluene (25 mL) and water (2.8 mL) to give a colorless solution. The reaction mixture was 3x degassed and purged with argon; then palladium(II) acetate (14.3 mg, 63.7 iimol, Eq: 0.02), potassium (4- cyanophenyl)trifluoroborate (732 mg, 3.5 mmol, Eq: 1.1, CAS Reg. No. 850623-36-8) and butyldi-l-adamantylphosphine (68.5 mg, 191 umol, Eq: 0.06, CAS Reg. No. 321921-71-5) were successively added. The degassing-purging cycle was repeated after each addition. The reaction mixture was then heated to 120 C for 5 hours. After cooling, the reaction mixture was poured onto 50mL [ LO and extracted with AcOEt (0147) (2x50mL). The organic layers were washed with H20/brine, combined, dried over Na2S04 and concentrated in vacuo. Purification by flash chromatography (silica gel, 50 g, 50% to 100 % CH2C12 in heptane) yielded finally 898mg of the title compound as white foam; MS (ESI) 337.2 (M+H)+.

Reference： [1]Patent: WO2013/37703,2013,A1 .Location in patent: Page/Page column 69
[2]Patent: US2013/65876,2013,A1 .Location in patent: Paragraph 0387-0388
[3]Patent: WO2020/21097,2020,A1 .Location in patent: Page/Page column 28

18
[ 10273-90-2 ]
[ 850623-36-8 ]
[ 1441122-38-8 ]

Yield	Reaction Conditions	Operation in experiment
48%	With sodium acetate; palladium diacetate; manganese triacetate; acetic acid; In 2,2,2-trifluoroethanol; at 50℃; for 18h;	General procedure: Substrate, solvent,NaOAc, Pd(OAc)2, and Mn(OAc)3*2H2O were combined in a 20 mLscintillation vial. The vial was sealed with a Teflon-lined cap andheated at 50C for 18 h with vigorous stirring. After cooling to roomtemperature, the reaction mixture was diluted with EtOAc (50 mL)and washed with 10 wt % aqueous Na2SO3 (115 mL), saturatedaqueous NaHCO3 (225 mL), and brine (110 mL). The combined aqueous layers were extracted with EtOAc (225 mL). The organiclayers were then combined, dried over MgSO4, filtered, and concentratedto afford the crude product, which was purified by columnchromatography on silica gel. The characterization data (1H and 13C NMR spectra, IR, and melting points, where appropriate) forpreviously reported products matched that reported in the literature.

Reference： [1]Tetrahedron,2013,vol. 69,p. 5580 - 5587

19
[ 138373-10-1 ]
[ 850623-36-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 6427 - 6439

20
[ 623-00-7 ]
[ 850623-36-8 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 6427 - 6439

21
[ 850623-36-8 ]
[ 1194-02-1 ]

Yield	Reaction Conditions	Operation in experiment
40%Spectr.	With lithium hydroxide monohydrate; silver trifluoromethanesulfonate; Selectfluor; In ethyl acetate; at 55℃;Sealed tube;	General procedure: Trifluoroborate (0.50 mmol, 1.0 equiv), LiOH·H2O (25.2 mg, 0.60 mmol, 1.2 equiv), Selectfluor (212 mg, 0.60 mmol, 1.2 equiv), AgOTf (386 mg, 1.5 mmol, 3.0 equiv) were weighed into a 20 mL microwave vial. EtOAc (5 mL) was added, and sealed with a microwave cap and the mixture was allowed to stir at 55 C for 5-15 h. The resulting solution was cooled to room temperature. For the compounds reported with isolated yields (2a, 2b, 2c, 2d, 2e, 2g, 2h, 2j, 2k, 2l, 2m, 2o, 2p, 2t, 2u, 2x, 2v, 2y, 2ab, 2ac, and 2ag) the reaction mixture was diluted with MTBE or hexane (5 mL) and H2O (4.0 mL). Then organic phase was separated, the aqueous phase was extracted with MTBE (2*5 mL). The combined organic phases were dried over anhydrous Na2SO4. The filtrate was concentrated in rotavapor and the residue was purified by column chromatography on Combiflash with hexanes/EtOAc to afford the desired compounds. The volatile and low yielding products were not isolated and their yields were determined only by 19F NMR of the reaction mixture. For the compounds reported with 19F NMR yields, 4-fluorobenzonitrile (0.50 mmol) was added as reference to the reaction mixture, stirred for 5 min, and then diluted with MTBE or hexane (5 mL) and H2O (3.0 mL). The layers were separated and an an aliquote of the organic phase was withdrawn for the 19F NMR measurement in CDCl3.
10%Spectr.	With iron(III) chloride; potassium fluoride; Selectfluor; In ethyl acetate; at 55℃;	General procedure: FeCl3 (60.8 mg, 0.375 mmol, 1.5 equiv), Selectfluor (177 mg, 0.5mmol, 2.0 equiv), and KF (43.6 mg, 0.75 mmol, 3.0 equiv) wereweighed into a 10-mL microwave vial. EtOAc (2.5 mL) was added, andthe vial was sealed with a septum. The mixture stirred at 25 C for 5min. Then, potassium aryltrifluoroborate (0.25 mmol, 1.0 equiv) wasadded to the mixture, and the vial was sealed with microwave capand the mixture stirred at 55 C for 10-15 h. The resulting solutionwas cooled to r.t.The volatile products were not isolated and their yields were determinedonly by 19F NMR of the reaction mixture. For the compoundsreported with 19F NMR yields, 4-fluorobenzonitrile (0.25 mmol) wasadded as reference to the mixture, stirred for 5 min, and then dilutedwith t-BuOMe or hexane (2.5 mL) and H2O (3.0 mL). The layers wereseparated and an organic aliquot was withdrawn for the 19F NMRmeasurement in either in CDCl3 or DMSO-d6. The 19F NMR spectroscopicdata were identical to those reported previously in the literature.The identity of the product was further confirmed by GC-MSanalysis. For the compounds reported as isolated yields, the mixture was dilutedwith t-BuOMe or hexane (2.5 mL) and H2O (4.0 mL). Then organicphase was separated, the aqueous phase was extracted with t-BuOMe(2 × 5 mL). The combined organic phases were dried (anhyd Na2SO4),the solvent was removed at 1.0 bar and the residue was purified bycolumn chromatography (Combiflash, hexanes) to afford the desiredcompounds. The identity of the product was confirmed by 1H NMRand GC-MS analyses.

Reference： [1]Journal of the American Chemical Society,2013,vol. 135,p. 16292 - 16295
[2]Tetrahedron,2014,vol. 70,p. 9676 - 9681
[3]Synthesis,2015,vol. 47,p. 854 - 860

22
[ 850623-36-8 ]
[ 1133116-39-8 ]
[ 1509948-71-3 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 10132 - 10141

23
[ 850623-36-8 ]
[ 1133116-39-8 ]
[ 1509948-96-2 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 10132 - 10141

24
[ 850623-36-8 ]
[ 2926-29-6 ]
[ 455-18-5 ]

Reference： [1]RSC Advances,2014,vol. 4,p. 6496 - 6499

25
[ 850623-36-8 ]
[ 119336-08-2 ]
N-tert-butyloxycarbonyl-m-(4-cyanophenyl)tyrosine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With palladium diacetate; potassium carbonate; In methanol; at 80℃; for 10h;Inert atmosphere;	General procedure: To a two-necked 25 mL round-bottomed flask undera nitrogen atmosphere containing Pd(OAc)2 (11.23 mg, 10 mol%), potassium trifluoroborate salt (0.5 mmol), L-N-t-butyloxycarbonyltyrosine methyl ester (210.5 mg,0.5 mmol), and dry MeOH (4 mL) were added K2CO3 (207.6 mg, 1.5 mmol). The reaction mixture was stirred and heated at 80 C. The reaction was monitored by thin layer chromatography (TLC). Then the reaction mixture was diluted with ethyl acetate and washed with saturated solution of NH4Cl (3 × 20 mL), the organic phase was collected, dried with MgSO4, filtered and the solvent was removed under vacuum. Purification by silica flash chromatography (eluting with ethyl acetate/hexane 2:8).

Reference： [1]Journal of the Brazilian Chemical Society,2015,vol. 26,p. 765 - 774

26
[ 850623-36-8 ]
[ 586-78-7 ]
[ 31835-63-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium diacetate; potassium carbonate; In ethanol; water; at 80℃; for 1h;	General procedure: A mixture of aryl bromides (0.5 mmol), potassium aryltrifluoroborates (0.6 mmol), K2CO3 (0.5 mmol), Pd(OAc)2 (1 mol %), EtOH/H2O (2 mL/2 mL) was stirred at 25 C in air for the indicated time. The reaction mixture was added to brine (15 mL) and extracted with ethyl acetate (3×15 mL). The solvent was concentrated under vacuum, and the product was isolated by short-column chromatography on silica gel (200-300 mesh).

Reference： [1]Tetrahedron,2015,vol. 71,p. 3954 - 3959

27
[ 850623-36-8 ]
[ 81755-10-4 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 5780 - 5783

28
[ 3058-39-7 ]
[ 850623-36-8 ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3676 - 3680

29
potassium hydrogen difluoride [ No CAS ]
[ 126747-14-6 ]
[ 850623-36-8 ]

Reference： [1]Chemical Science,2016,vol. 7,p. 3676 - 3680

30
[ 850623-36-8 ]
[ 18523-41-6 ]

Yield	Reaction Conditions	Operation in experiment
17%	With potassium azide; copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 25℃;Sealed tube;	General procedure: The aryl trifluoroborate substrate (0.5 mmol, 1 equiv), Cu(OTf)2 (723 mg, 2 mmol, 4equiv), and potassium azide (162 mg, 2 mmol, 4 equiv) were weighed into a 20 mL vialequipped with a magnetic stir bar. CH3CN (6 mL) was added, and the vial was sealedwith a Teflon-lined cap. The reaction mixture was allowed to stir at room temperature for12 h. For pyridine substrates, after 12 h, 1 g of poly(4-vinylpyridine) was added to thesolution, and the resulting mixture was stirred for 12 h at room temperature. Theresulting solution was diluted with diethyl ether (10 mL), and the organic layer wasextracted with water (3 x 10 mL). The organic layer was dried over MgSO4, filtered, andconcentrated under reduced pressure. The products were purified by columnchromatography on silica.

Reference： [1]Synlett,2016,vol. 27,p. 2279 - 2284

31
[ 850623-36-8 ]
[ 1184-88-9 ]
[ 180143-65-1 ]

Yield	Reaction Conditions	Operation in experiment
56%	With copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 25℃; for 16h;Sealed tube;	General procedure: The aryl trifluoroborate substrate (0.5 mmol, 1 equiv), Cu(OTf)2 (723 mg, 2 mmol, 4equiv) and sodium pivalate (248 mg, 2 mmol, 4 equiv) were weighed into a 20 mL vialequipped with a magnetic stir bar. CH3CN (6 mL) was added, and the vial was sealedwith a Teflon-lined cap. The reaction mixture was allowed to stir at room temperature for16 h. For pyridine substrates, after 16 h, 1 g of poly(4-vinylpyridine) was added to thesolution, and the resulting mixture was stirred for an additional 12 h at roomtemperature. The resulting solution was diluted with diethyl ether (10 mL), and then theorganic layers were extracted with water (3 x 10 mL) and with a 1 M aqueous NH4OHsolution, saturated with EDTA (10 mL). The organic layer was dried over MgSO4,filtered, and concentrated under pressure. The products were purified by columnchromatography on silica.

Reference： [1]Synlett,2016,vol. 27,p. 2279 - 2284

32
[ 850623-36-8 ]
[ 67-66-3 ]
[ 624-31-7 ]
[ 35776-95-5 ]

Reference： [1]Green Chemistry,2016,vol. 18,p. 5782 - 5787

33
[ 3480-65-7 ]
[ 850623-36-8 ]
4-(2-oxo-2H-[1,2'-bipyridin]-6-yl)benzonitrile [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5376 - 5379

34
[ 850623-36-8 ]
2-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ol [ No CAS ]
2-(4-(cyanophenyl)-1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium carbonate; In water; acetonitrile; at 100℃;Inert atmosphere;	General procedure: A 25 mL two necked roundbottom flask (the reaction vessel) equipped with a magnetic stirrerbar was charged with 2-(4-chloro-1H-pyrrolo[3,2-c]pyridin-2-yl)propan-2-ol 16 (25.0 mg, 119 mmol, 1.0 equiv), dicyclohexyl(20,6'-dimethoxy-[1,1'-biphenyl]-2-yl)phosphine (SPhos) (1.23 mg,2.97 mmol, 0.025 equiv) potassium carbonate (49.2 mg, 356 mmol,3.0 equiv), palladium(II) acetate (2.66 mg, 11.9 mmol, 0.1 equiv) andpotassium organotrifluoroborate (1.5 equiv) and placed under nitrogen.Acetonitrile and water (3/2 v/v), in a separate 50 mL singlenecked round bottom flask, was degassed with three freeze-pumpthawcycles. The degassed acetonitrile/water (1.98 mL(1.19 mL + 0.79 mL)) was then added to the reaction vessel via agraduated pipette. The reaction mixture was then heated at 100 C under nitrogen with magnetically facilitated stirring for the timeindicated in Table 1, at which point tlc and GC/MS (EI) analysisshowed that the starting material 16 had been consumed. The reactionmixture was cooled and transferred to a separating funnelwith the assistance of ethyl acetate (25 mL) and water (25 mL). Themixture was shaken, the layers were separated and the aqueouslayer was extracted with ethyl acetate (3 x 25 mL), with shaking.The organic layers were combined and dried over magnesiumsulfate and the solvent was removed via rotary evaporation. Theresidue was purified by flash column chromatography over silicausing n-hexane/ethyl acetate (99:1 to 0:100) mixtures or n-hexane/ethyl acetate (99:1 to 0:100) followed by ethyl acetate/methanol(100:0 to 75:25) mixtures as eluent to give the 4-substituted 2-(1Hpyrrolo[3,2-c]pyridin-2-yl)propan-2-ols (17-32).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 128,p. 202 - 212

35
[ 4053-40-1 ]
[ 850623-36-8 ]
8-(4-cyanophenyl)-4-methylquinoline N-oxide [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 3029 - 3034

36
[ 850623-36-8 ]
[ 38318-52-4 ]
diethyl (1-(4-cyanophenyl)vinyl)phosphonate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2017,vol. 15,p. 8985 - 8989

37
[ 850623-36-8 ]
[ 63468-90-6 ]
[ 1503-49-7 ]

Reference： [1]RSC Advances,2017,vol. 7,p. 51928 - 51934

38
[ 850623-36-8 ]
[ 59-88-1 ]
[ 2920-38-9 ]

Reference： [1]Applied Organometallic Chemistry,2018,vol. 32

39
[ 850623-36-8 ]
[ 36602-01-4 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1667 - 1671

40
[ 850623-36-8 ]
[ 31125-07-2 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 1667 - 1671

Yield	Reaction Conditions	Operation in experiment
90%	for 0.3h;	General procedure: Arylboronic acid (1 molar amount), potassium hydrogendifluoride (3 times molar amount), stirred at 500 rpm for 10 minutes at high speed to obtain a mixed homogeneous powdery material.The feed port of the twin-screw extruder was continuously added, and the extrusion time was set to 8 minutes.The extruded material is directly received in a receiver containing the same weight of water as the solid material, stirred and dispersed to obtain a slurry, filtered, and the filtrate is returned to receive.,The filter cake was washed with water and dried by hot air to obtain an aryltrifluoroborate product (Table 1).

42
[ 850623-36-8 ]
C₃₅H₄₀IN₅O₈ [ No CAS ]
C₄₂H₄₄N₆O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; In methanol; at 60℃; for 10h;Inert atmosphere;	General procedure: To a two-necked 25 mL round-bottomed flask under a nitrogenatmosphere containing Pd(OAc)2 (2.2 mg, 10 mol%),potassium trifluoroborate salt (0.12 mmol), dipeptide III(58.4 mg, 0.1 mmol), and dry MeOH (3 mL) was addedCs2CO3 (32.5 mg, 0.1 mmol). The reaction mixture wasstirred and heated at 60C. The reaction was monitored byTLC (10 hours). Then the reaction mixture was diluted withethyl acetate and washed with saturated solution of NH4Cl (3X 20 mL), the organic phase was collected, dried withMgSO4, filtered and the solvent was removed under vacuum.Purification was achieved by silica flash chromatography(eluting with ethyl acetate / hexane 5:5).

Reference： [1]Medicinal Chemistry,2018,vol. 14,p. 709 - 714

43
[ 850623-36-8 ]
5-phenyldipyrromethane [ No CAS ]
(4-cyanophenyl)fluoro[(Z)-2-(phenyl(2H-pyrrol-2-ylidene-κN)methyl)-1H-pyrrolato-κN]boron [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7767 - 7770

44
[ 850623-36-8 ]
3,3’,5,5’-tetramethyl-2-dipyrromethene trifluoroacetic acid [ No CAS ]
(4-cyanophenyl)fluoro[(Z)-2-((3,5-dimethyl-2H-pyrrol-2-ylidene-κN)methyl)-3,5-dimethyl-1H-pyrrolato-κN]boron [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7767 - 7770

45
[ 626-55-1 ]
[ 850623-36-8 ]
4-(pyridine-3-yl)benzonitrile [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33

46
potassium fluoride [ No CAS ]
[ 126747-14-6 ]
[ 850623-36-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3548 - 3553

47
[ 850623-36-8 ]
4-(benzyloxy)-N-methoxybutanamide [ No CAS ]
4-(benzyloxy)-N-(4-cyanophenyl)butanamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 7941 - 7947

48
[ 850623-36-8 ]
4-(4-methoxyphenyl)-2,3-bis(phenylselanyl)-4H-selenochromene [ No CAS ]
4-(4-(4-methoxyphenyl)-3-(phenylselanyl)-4H-selenochromen-2-yl)benzonitrile [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3163 - 3172

49
[ 850623-36-8 ]
N’-(6-chloropyridazin-3-yl)-5-(4-cyanophenyl)-N'-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carbohydrazide [ No CAS ]

Reference： [1]Patent: WO2020/21097,2020,A1

50
[ 850623-36-8 ]
[ 10540-31-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 1.5 h / 0 - 20 °C / Schlenk technique; Inert atmosphere 2: 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; oxygen / acetonitrile / 16 h / 50 °C / Inert atmosphere; Irradiation

Reference： [1]Music, Arif; Baumann, Andreas N.; Boser, Florian; Müller, Nicolas; Matz, Florian; Jagau, Thomas C.; Didier, Dorian [Chemistry - A European Journal, 2021, vol. 27, # 13, p. 4322 - 4326]

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 850623-36-8 ] {[proInfo.proName]}

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[ 850623-36-8 ] Synthesis Path-Upstream 1~1

[ 850623-36-8 ] Synthesis Path-Downstream 1~50

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Fluorinated Building Blocks

Aryls

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