Name: 757978-19-1|5-Bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine|98%
Brand: Ambeed
SKU: A584533
Price: 29.0 USD
Availability: InStock
Rating: 99 (40 reviews)

1
[ 757978-19-1 ]
[ 1001412-05-0 ]
[ 1001414-15-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium carbonate; triphenylphosphine In water; acetone at 75℃; for 1h;	80.2; 91.1 Into a vial was dissolved l-benzenesulfonyl-5-bromo-3-iodo-lH-pyrrolo[2,3-b]pyridine (581 mg, 0.00125 mol) and 3-([l-(3,4-Dtfluoro-berizyl)-2-oxo-l,2-dihyd^o-pyridine-3- carbonyl]-amino}-methyl)-phenylboronic acid (453 mg, 0.00114 mol) and palladium acetate (13 mg, 0.000057 mol; Strem) and triphenylphosphine (32 mg, 0.00012 mol; Aldrich) in acetone (5.4 mL, Acros; ). To this was added 2.0 M of sodium carbonate in water (1.8 mL). The vial was flushed under an atmosphere of argon and sealed and was heated at 75 Celsius for 1 hour. The reaction was evaporated then diluted with methylene chloride, washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.33 in 1:3 hexanes/ethyl acetate) to yield 663.8 mg (85 %) of product. MS m/z=689.09 M+H. .; Into a vial was dissolved l-benzenesulfonyl-5-bromo-3-iodo-lH-pyϖOlo[2,3-b]pyridiϖe (581 mg, 0.00125 mol), S-Clfl-CS^-Difluoro-benzy^^-oxo-l^-dihydro-pyridine-S-carbonyl]- amino}-methyl)-phenylboronic acid (453 mg, 0.00114 mol), palladium acetate (13 mg, 0.000057 mol; Strem) and triphenylphosphine (32 mg, 0.00012 mol; Aldrich) in acetone (5.4 mL, Acros). To this was added 2.0 M sodium carbonate in water (1.8 mL, 0.0036 mol). The vial was flushed with argon, sealed, and was heated at 75 Celsius for 1 hour. The reaction was evaporated, then was diluted with methylene chloride, washed with water, dried with magnesium sulfate, filtered, and concentrated. The residue was taken up in methylene chloride and purified by silica gel chromatography using hexanes/ethyl acetate as eluent (Rf=0.33 in 1 :3 hexanes/ethyl acetate) to yield 663.8 mg (85 %) of the title compound. MS m/z=689.09 M+H.

Reference： [1]Current Patent Assignee: VIRACTA THERAPEUTICS INC - WO2008/5457, 2008, A2 Location in patent: Page/Page column 134

2
[ 757978-18-0 ]
[ 98-09-9 ]
[ 757978-19-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; for 2.75h;	To a cooled solution of 45 (15.00 g, 46.6 mmol) in CH2C12 (210 ML) was added benzenesulfonyl chloride (9. 18 mL, 71. 8 mmol), 50% aq NAOH (13.04 mL) and Bu4NHSO4 (2.35 g, 6.94 mmol). The mixture was allowed to warm to ambient temperature and stirred for 2 h 45 min. The mixture was diluted with CH2C12 (200 mL) and washed with saturated brine solution (200 ML). The aqueous layer was extracted with CH2C12 (2x 200 mL), the combined organics were dried (MGSO4) and concentrated to afford a pale yellow solid. The solid was stirred vigorously with cold methanol for 1 h and the resulting precipitate was filtered off and dried under vacuum to afford 46 as a white solid (20. 90 g, 97%); 1H NMR (400 MHz, CDCl3) 6 7.49 (t, J = 15.5, 7.4 Hz, 2H), 7.60-7. 64 (m, 1H), 7. 81 (d, J = 2.2 Hz, 1H), 7.87 (s, 1H), 8.17-8. 19 (m, 2H), 8.45 (d, J = 2. 1 Hz, 1H).
97%		To a solution of <strong>[757978-18-0]3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine</strong> (500 mg, 1.55 mmol) in CH2Cl2 (4.1 ml) are added 60% sodium hydride (186 mg, 4.66 mmol) and benzyltriethylammonium chloride (8 mg, 0.03 mmol) under argon at 0 C. After 30 minutes, benzenesulfonyl chloride (240 mul, 1.86 mmol) is added at 0 C. and the mixture is stirred at room temperature for 2 hours. The mixture is neutralized with water and extracted several times with CH2Cl2. The organic phases are combined, dried on MgSO4 and concentrated under reduced pressure. The residue is precipitated with methanol and the resulting solid filtered to yield the expected product in the form of a pink solid with 97% yield. 1H NMR (CDCl3, 500 MHz) delta 8.46 (d, J=2.0 Hz, 1H), 8.19 (d, J=8.0 Hz, 2H), 7.88 (s, 1H), 7.82 (d, J=2.5 Hz, 1H), 7.64-7.61 (m, 1H), 7.54-7.51 (m, 2H); 13C NMR (CDCl3, 75 MHz) delta 146.7, 144.7, 137.6, 134.6, 132.5, 131.2, 129.2, 128.2, 126.7, 116.0, 60.6. (0130) HRMS (ESI+) calculated for C13H9N2O2S79Br[M+H]+ 462.8613. found 462.8605, HRMS (ESI+) calculated for C13H9N2O2S81Br[M+H]+ 464.8592. found 464.8596. IR (cm-1): v 2851, 1613, 1370.
80%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; at 20℃; for 12h;	Method A-9Synthesis of intermediate V-02V-01 V-02 To a solution of 5-bromo-3-iodo-1H-pyrrolo[2,3-jb]pyridine V-01 (1.58 g, 4.64 mmol) in DCM (47 mL) was added benzenesulfonyl chloride (1.32 mL, 10.22 mmol), tetrabutylammonium hydrogen sulfate (55% in water , 0.75 mL, 1.16 mmol) and NaOH (50% aq., 14 mL). The reaction mixture was stirred at RT for 12 h. The mixture was quenched with brine and the aqueous layer was extracted with DCM (2 x 20 mL). The combined organic layers were dried over Na2S04, filtered and evaporated. Ice-cold methanol was added to the residue and the mixture was stirred at 0C for 1 h. The suspension was filtered off and the solid was washed with ice-cold methanol to afford Intermediate V-02 (1.72 g, 80%) as a pale yellow solid.

61%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In dichloromethane; water; at 20℃; for 2h;Inert atmosphere;	5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0253) To a solution of <strong>[757978-18-0]5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine</strong> (2.5 g, 7.7 mmol) in dichloromethane (35 mL) was added benzenesulfonyl chloride (2.2 g, 12.5 mmol) and Bu4NHSO4 (340 mg, 1.00 mmol) at room temperature. Then a solution of sodium hydroxide (2.5 g, 62.5 mmol) in water (5 mL) was added. The resulting mixture was then stirred for 2 h at room temperature. The reaction mixture was extracted with dichloromethane (10 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was recrystallized from methanol to yield 1-(benzenesulfonyl)-<strong>[757978-18-0]5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine</strong> as brown solid (2.2 g, 61%). MS: m/z=462.0 [M+H]+.
	With dmap; triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with ice;	100 mL round bottom flaskIodo-1H-pyrrole [2,3-b] pyridine (M1) (100.0 mg, 3.1 mmol)20 mL of dichloromethane, triethylamine (930 mg, 9.2 mmol), DMAP (40 mg, 0.31 mmol),Benzenesulfonyl chloride (N1) (1100 mg, 6.2 mmol) was dissolved in 10 mL of dichloromethane under ice-cooling,Dropping funnel through the constant pressure drop into the solution, the drop is completed, stirring at room temperature 1h,TLC detection, no M1 remaining, washed 3 times, liquid separation, the organic phase anhydrous sodium sulfate drying,The solvent was removed by concentration and recrystallized from ethyl acetate (5 mL) to give a white solid which was dried to give 5-bromo-3-iodo-1- (phenylsulfonyl) -1H-pyrrole [2,3-b] pyridine (B8).
		Synthesis of 1-(benzenesulfonyl)-5-bromo-3-iodo-pyrrolo[2,3-b]pyridine (12) To a solution of <strong>[757978-18-0]5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine</strong> (2.7 g, 8.36 mmol) in DMF (30.0 mL) was added sodium hydride (60%, 0.37 g, 9.2 mmol) at room temperature. After 10 minutes, benzenesulfonyl chloride (1.13 ml, 8.78 mmol) was added to and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured in to water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated, filtered and washed with ethyl acetate to obtain the desired product 12 as a white solid (2.70 g). The mother liquid was purified with silica gel column chromatography using 20% to 100% ethyl acetate in hexane as an eluent to give addition product (0.90 g). The combined yield is 93.0%. MS (ESI) [M+H+]+=464.1. 1H NMR spectrum is consistent with the structure of the compound.

Reference： [1]Patent: WO2004/78756,2004,A2 .Location in patent: Page 126-127
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 9569 - 9585
[3]Patent: US2015/307492,2015,A1 .Location in patent: Paragraph 0126-0131
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7212 - 7215
[5]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 875 - 880
[6]Patent: WO2012/156756,2012,A2 .Location in patent: Page/Page column 98
[7]Patent: US2016/376283,2016,A1 .Location in patent: Paragraph 0252; 0253
[8]Patent: CN106117181,2016,A .Location in patent: Paragraph 0146; 0147; 0148
[9]Patent: US2017/157120,2017,A1 .Location in patent: Paragraph 0459-0460

3
[ 757978-19-1 ]
[ 207307-51-5 ]
[ 757978-20-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium carbonate; lithium chloride In ethanol; water; toluene for 1.75h; Heating / reflux;	1-Benzenesulfonyl-5-bromo-3-(1-trityl-1H-pyrazol-4-yl)-1H-pyrrolo [2,3- pyridine (47) A mixture of 46 (1 g, 2.16 MMOL), EtOH (14 ML), toluene (14 mL), 1-TRITYL- lH-pyrazole-4-boronic acid (767 mg, 2.16 MMOL), 1M AQ. NA2CO3 (5.4 ML, 5. 4 MMOL), LiCI (275 mg, 6.5 mmol) and PDCL2 (PPH3) 2 (75 mg, 0. 108 mmol) was refluxed for 1 h 45 min. The reaction mixture was concentrated to afford a pale yellow solid. The solid was purified by silicagel chromatography (Si 50 g column) using 30% ethyl acetate in hexane as eluent (gradient elution) to give the product 47 (798 mg, 57%) as a pale yellow solid ; 1H NMR (400 MHz, CDCl3) No. 7. 18-7. 23 (M, 6H), 7.33-7. 37 (M, 9H), 7.47 (T, J= 15.6, 7.4 Hz, 2H), 7.57-7. 60 (M, 2H), 7.74 (s, 1H), 7.91 (s, 1H), 7.95 (d, J= 2.1 Hz, 1H), 8. 15- 8. 18 (m, 2H), 8.46 (d, J = 2.2 Hz, 1H).

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2004/78756, 2004, A2 Location in patent: Page 126-128

4
[ 757978-19-1 ]
[ 536-74-3 ]
1-benzenesulfonyl-5-bromo-3-phenylethynyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With copper(l) iodide; triethylamine at 80℃; for 1h;	Synthesis of example inhibitor 22; 1-Benzenesulfonyl-5-bromo-3-phenylethynyl-1H-pyrrolo [2, 3-B] PYRIDINE (20). A mixture of iodide 19 (300 mg, 0.647 mmol; preparation disclosed in PCT/GB2004/000944), PDCL2 (PPH3) 2 (45 mg, 0.064 mmol), Cul (21 mg, 0.110 mmol) and phenylacetylene (142 LIL, 1.295 mmol) in Et3N (11.2 mL) was stirred for 1 h at 80 °C. The reaction mixture was then evaporated to dryness and purified by preparative LCMS (column LUNA 10 R C18 (2) OOG-4253-VO 250x50 mm) using water-acetonitrile (0. 1% ACOH) as eluent (in gradient; flow 80 mL/min) to give the product 20 as a yellow solid (53 mg, 19%) ; H NMR (400 MHz, CDC13) 6 7.33-7. 39 (M, 3H), 7.52-7. 62 (M, 5H), 7.96 (s, 1H), 8.14 (d, J = 2.18 Hz, 1H), 8.16-8. 21 (m, 2H), 8.50 (d, J =2.17 Hz, 1H).

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2004/101565, 2004, A2 Location in patent: Page 50

5
[ 757978-19-1 ]
[ 121359-48-6 ]
[ 1046793-47-8 ]

Yield	Reaction Conditions	Operation in experiment
44%	In toluene at 110℃; for 6h;	A Procedure A involving (IV-a)(\|V-a) C")A stirred solution of (IV-a) (10 mmol; preparation disclosed in WO2004/078756), trialkylstannane (V) (10 mmol), tri-o-tolylphosphine (380 mg, 1.25 mmol) and bis(acetonitrile)dichloropalladium (II) (160 mg, 0.62 mmol) in toluene (32 mL) was refluxed for 6 h (bath temperature 1 1O0C). The reaction mixture was then cooled, diluted with AcOEt (210 mL) and washed with saturated aqueous NaHCO3 (2 x 50 mL). The organic layer was dried (MgSO4) and concentrated. The residue was purified by silicagel chromatography (SGC) using an appropriate solvent system as eluent. Yield 44%.; 2-(5-bromo-l-(phenylsulfonyl)-lH-pyrrolo[2,3-b]pyridin-3-yl)thiazole (III-j)(\|V"a) ("H)Bromide (IV-a) (4.35 g, 9.39 mmol; preparation disclosed in WO2004/078756), 2-(tributylstannyl)thiazole (3.71 g, 9.92 mmol), tri-o- tolylphosphine (355 mg, 1.17 mmol) and bis(acetonitrile)dichloropalladium (II) (150 mg, 0.58 mmol) in toluene (30 mL) were reacted for 6 h (bath temperature 11O0C) using the general procedure A for the Stille reaction. The crude product (dark brown oil, 8.89 g) was purified by silicagel chromatography using CH2Cl2 as eluent to afford the (III-j) as a pale yellow foam (1.72 g, 4.09 mmol, 44%). 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J = 3.3 Hz, IH), 7.55 (t, J = 7.7 Hz, 2H), 7.65 (tt, J = 1.5, 7.5 Hz, IH), 7.91 (d, J= 3.3 Hz, IH), 8.22 - 8.29 (m, 3H), 8.55 (d, J= 2.2 Hz, IH), 8.83 (d, J= 2.2 Hz, IH).

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2008/95943, 2008, A1 Location in patent: Page/Page column 53; 169

6
[ 757978-19-1 ]
[ 30418-59-8 ]
C₁₉H₁₄BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Hong, Seunghee; Lee, Soyoung; Kim, Bomi; Lee, Hyunseung; Hong, Soon-Sun; Hong, Sungwoo [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7212 - 7215]
[2]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

7
[ 757978-19-1 ]
[ 1692-25-7 ]
C₁₈H₁₂BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Hong, Seunghee; Lee, Soyoung; Kim, Bomi; Lee, Hyunseung; Hong, Soon-Sun; Hong, Sungwoo [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7212 - 7215]
[2]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[3]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

8
[ 757978-19-1 ]
[ 122775-35-3 ]
3-(3,4-dimethoxyphenyl)-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; for 3.5h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]
[2]Hong, Seunghee; Lee, Soyoung; Kim, Bomi; Lee, Hyunseung; Hong, Soon-Sun; Hong, Sungwoo [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7212 - 7215]
[3]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[4]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[5]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

9
[ 757978-19-1 ]
[ 150255-96-2 ]
C₂₀H₁₂BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Hong, Seunghee; Lee, Soyoung; Kim, Bomi; Lee, Hyunseung; Hong, Soon-Sun; Hong, Sungwoo [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 24, p. 7212 - 7215]
[2]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[3]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

10
[ 757978-19-1 ]
[ 1261082-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

11
[ 757978-19-1 ]
[ 1261082-86-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

12
[ 757978-19-1 ]
[ 1261082-88-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

13
[ 757978-19-1 ]
[ 1290143-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

14
[ 757978-19-1 ]
[ 1377503-75-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

15
[ 757978-19-1 ]
[ 1377503-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

16
[ 757978-19-1 ]
[ 1377503-48-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

17
[ 757978-19-1 ]
[ 1377503-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 3 h / 80 °C / Inert atmosphere 2: water; potassium hydroxide / 1,4-dioxane / 0.5 h / 80 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium carbonate / 1,4-dioxane; water / 5 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere

Reference： [1]Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]

18
[ 757978-19-1 ]
[ 1692-15-5 ]
[ 1377503-76-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]

19
[ 757978-19-1 ]
[ 98-80-6 ]
3-phenyl-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; for 3.5h; Inert atmosphere;
89%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; for 3.5h; Inert atmosphere;	1 3-phenyl-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine To a solution of 3-iodo-5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (250 mg, 0.54 mmol) in a 3:1 toluene/ethanol mixture (17 ml) are added benzene boronic acid (65 mg, 0.54 mmol), K2CO3 (1.6 ml of 2 M solution in water, 3.20 mmol) and Pd(PPh3)4 (1.5 mol %) and the reaction is heated at 110° C. for 3.5 hours under argon. (0134) The mixture is cooled to room temperature, concentrated under a vacuum and redissolved in a water/CH2Cl2 mixture. The aqueous phase is extracted several times with CH2Cl2 and the combined organic phases are dried on MgSO4. The solvent is evaporated under reduced pressure and the residue purified by flash chromatography on silica gel (100% CH2Cl2) to yield the purified product in the form of a white solid with 89% yield. 1H NMR (CDCl3, 300 MHz) δ 8.50 (d, J=2.1 Hz, 1H), 8.25-8.20 (m, 3H), 7.90 (s, 1H), 7.64-7.36 (m, 8H); 13C NMR (CDCl3, 75 MHz) δ 145.7, 145.6, 137.9, 134.3, 131.8, 131.1, 129.1, 129.0, 128.0, 127.9, 127.3, 123.9, 123.1, 119.8, 115.5. (0137) HRMS (ESI+) calculated for C19H14N2O2S79Br [M+H]+ 412.9959. found 412.9969, HRMS (ESI+) calculated for C19H14N2O2S81Br [M+H]+ 414.9939. found 412.9958. (0138) IR (cm-1): v 2919, 1605, 1383.
70%	With potassium carbonate; palladium dichloride In 1,4-dioxane; water at 40℃; for 24h; Inert atmosphere;	Step 2. Add the compound 5-bromo-3-iodo-1-(benzenesulfonyl)-1H-7-azaindole (1.000g, 2.16mmol) into a 50mL round-bottomed flask under a nitrogen atmosphere,Phenylboronic acid (0.268g, 2.20mmol),Anhydrous potassium carbonate (0.900g, 6.60mmol), water (5.00mL), 1,4-dioxane (25.00mL) and catalyst PdCl2(dppf) (0.06g, 8.8×10-2mmol),Then react at 40°C for 24 hours, cool to room temperature, dilute with water, neutralize with 6M hydrochloric acid to pH=5-6, extract with dichloromethane (25mL*2), wash the organic phase with water, wash with saturated brine, and anhydrous sulfuric acid Dry with sodium, concentrate under reduced pressure, and purify by column chromatography to obtain the target product5-Bromo-3-phenyl-1-(bensulfonyl)-1H-7-azaindole (Yield, 70%).

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]
[2]Current Patent Assignee: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF REIMS CHAMPAGNE-ARDENNE; PARIS CITE UNIVERSITY - US2015/307492, 2015, A1 Location in patent: Paragraph 0132-0138
[3]Current Patent Assignee: FUDAN UNIVERSITY - CN113214247, 2021, A Location in patent: Paragraph 0139-0140; 0142
[4]Location in patent: experimental part Hong, Seunghee; Kim, Jinhee; Seo, Ju Hyeon; Jung, Kyung Hee; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5337 - 5349]

20
[ 757978-19-1 ]
[ 1003846-21-6 ]
1-(benzenesulfonyl)-5-bromo-3-(1-tetrahydropyran-2-ylpyrazol-4-yl)pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium(0); sodium hydrogencarbonate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	[0254] Step 1 : l-(Benzenesulfonyl)-5-bromo-3-(l-tetrahydropyran-2-ylpyrazol-4- yl)pyrrolo[2,3-b]pyridine. A solution of l-(benzenesulfonyl)-5-bromo-3-iodo-pyrrolo[2,3- b]pyridine (2.0 g, 4.3 mmol), l-tetrahydropyran-2-yl-4-(4,4, 5,5 -tetramethyl- 1,3,2- dioxaborolan-2-yl)pyrazole (1.8 g, 6.4 mmol) and NaHC03 ( 0.72 g, 8.6 mmol) in dioxane/water (3: 1, 32 mL) was sparged with N2 (g) for 5 min. Tetrakis palladium triphenylphosphine (0.05 g, 0.43 mmol) was added and the reaction mixture heated to 90 C overnight. The reaction was cooled to rt, water (5 mL) and EtOAc (25 mL) were added, the layers separated and the aq. layer extracted with EtOAc (2 x 50 mL). The organic layers were combined, dried, filtered and evaporated. Purification of the residue by column chromatography (EtOAc/Hexanes) afforded the desired product (1.5 g, 71%). 1H NMR (DMSO-de) delta 8.65 (d, IH), 8.62 (s, IH), 8.52 (d, IH), 8.34 (s, IH), 8.15 (d, IH), 8.11-8.08 (m, 2H), 7.73 (dt, IH), 7.63 (dt, 2H), 5.43 (dd, IH), 3.96 (d, IH), 3.68-3.62 (m, IH), 2.33- 2.16 (m, IH), 1.95 (t, 2H), 1.76-1.65 (m, IH), 1.59-1.53 (m, 2H). LC-MS [M+H]+ 489.1.

Reference： [1]Patent: WO2014/4863,2014,A2 .Location in patent: Paragraph 0254

21
[ 757978-19-1 ]
[ 1003846-21-6 ]
1-(benzenesulfonyl)-5-(3,4-dimethoxyphenyl)-3-(1-tetrahydropyran-2-ylpyrazol-4-yl)pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Patent: WO2014/4863,2014,A2

22
[ 757978-19-1 ]
[ 1492681-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethanol; water / 2 h / 85 °C / Inert atmosphere 2: sodium hydroxide; water / methanol / 80 °C
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

23
[ 757978-19-1 ]
[ 98-80-6 ]
[ 1492680-20-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With palladium diacetate; sodium carbonate; triphenylphosphine In water; acetone at 85℃; for 2h; Inert atmosphere;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]

24
[ 757978-19-1 ]
[ 5720-07-0 ]
[ 1492680-42-8 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 85℃; for 2h; Inert atmosphere;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]

25
[ 757978-19-1 ]
[ 5720-07-0 ]
[ 1492680-76-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 110℃; for 3.5h; Inert atmosphere;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]
[2]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[3]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

26
[ 757978-19-1 ]
[ 10365-98-7 ]
[ 1492681-14-7 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 85℃; for 2h; Inert atmosphere;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]

27
[ 757978-19-1 ]
[ 122775-35-3 ]
[ 1492680-51-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 85℃; for 2h; Inert atmosphere;

Reference： [1]Gourdain, Stéphanie; Dairou, Julien; Denhez, Clément; Bui, Linh Chi; Rodrigues-Lima, Fernando; Janel, Nathalie; Delabar, Jean M.; Cariou, Kevin; Dodd, Robert H. [Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9569 - 9585]

28
[ 757978-19-1 ]
[ 1615223-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

29
[ 757978-19-1 ]
[ 1615223-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

30
[ 757978-19-1 ]
[ 1615223-25-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

31
[ 757978-19-1 ]
[ 1615223-26-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

32
[ 757978-19-1 ]
[ 1615223-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

33
[ 757978-19-1 ]
[ 1615223-28-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

34
[ 757978-19-1 ]
[ 1615223-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

35
[ 757978-19-1 ]
[ 1615223-17-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

36
[ 757978-19-1 ]
[ 1615223-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

37
[ 757978-19-1 ]
[ 1615223-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

38
[ 757978-19-1 ]
[ 1615223-35-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium acetate / 1,4-dioxane / 12 h / 90 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

39
[ 757978-19-1 ]
[ 1615223-19-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; potassium acetate / 1,4-dioxane / 12 h / 90 °C / Inert atmosphere 4: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 12 h / 90 °C / Inert atmosphere 4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

40
[ 757978-19-1 ]
[ 1615223-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

41
[ 757978-19-1 ]
[ 1615223-33-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

42
[ 757978-19-1 ]
[ 1615223-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

43
[ 757978-19-1 ]
[ 1112863-84-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

44
[ 757978-19-1 ]
[ 1615223-21-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

45
[ 757978-19-1 ]
[ 1615223-22-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

46
[ 757978-19-1 ]
[ 1615223-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 20 - 60 °C / Inert atmosphere 3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂; caesium carbonate / 1,4-dioxane; water / 2 h / 80 °C / Inert atmosphere; Sealed tube 2: potassium hydroxide / methanol / 1 h / 60 °C / Inert atmosphere 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane; water / 3 h / 100 °C / Inert atmosphere

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

47
[ 757978-19-1 ]
[ 182163-96-8 ]
C₂₂H₁₉BrN₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

48
[ 757978-19-1 ]
[ 149507-26-6 ]
C₂₀H₁₄BrFN₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Park, Hwangseo; Lee, Soyoung; Lee, Suhyun; Hong, Sungwoo [Organic and Biomolecular Chemistry, 2014, vol. 12, # 26, p. 4644 - 4655]
[2]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

49
[ 757978-19-1 ]
[ 5570-18-3 ]
C₁₉H₁₄BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

50
[ 757978-19-1 ]
[ 1679-18-1 ]
C₁₉H₁₂BrClN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

51
[ 757978-19-1 ]
[ 5720-05-8 ]
C₂₀H₁₅BrN₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

52
[ 757978-19-1 ]
[ 10365-98-7 ]
C₂₀H₁₅BrN₂O₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

53
[ 757978-19-1 ]
[ 10365-98-7 ]
3-(3,4-dimethoxyphenyl)-5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

54
[ 757978-19-1 ]
[ 192182-54-0 ]
C₂₁H₁₇BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;

Reference： [1]Lee, Soyoung; Lee, Hyunseung; Kim, Jinhee; Lee, Suhyun; Kim, Soo Jung; Choi, Byong-Seok; Hong, Soon-Sun; Hong, Sungwoo [Journal of Medicinal Chemistry, 2014, vol. 57, # 15, p. 6428 - 6443]

55
[ 757978-19-1 ]
2-tetrahydropyran-4-yloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile [ No CAS ]
5-[1-(benzenesulfonyl)-5-bromopyrrolo[2,3-b]pyridin-3-yl]-2-tetrahydropyran-4-yloxypyridine-3-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 40 - 80℃; Inert atmosphere;	11 0365] A suspension, kept under nitrogen, of 1.11 g (2.41 mmol) of 1-(benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine, 864 mg (2.65 mmol) of 2-tetrahydropyran-4-yloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carbonitrile and 243 mg (2.89 mmol) of sodium hydrogencarbonate in 5 ml of DMF and 2.5 ml of water is warmed to 40° C. with stirring. 34 mg (0.05 mmol) of bis(triphenylphosphine)palladium(II) chloride are then added. The reaction mixture is heated to 80° C. and stirred at this temperature for 18 hours. The reaction mixture is cooled to room temperature, and water is added. The precipitate formed is filtered off with suction, washed with water and chromatographed on a silica-gel column with cyclohexane/ethyl acetate as eluent: 5-[1-(benzenesulfonyl)-5-bromopyrrolo[2,3-b]pyridin-3-yl]-2-tetrahydropyran-4-yloxypyridine-3-carbonitrile as beige powder; HPLC/MS (A): 3.33 min, [M+H] 539/541.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2014/323481, 2014, A1 Location in patent: Paragraph 0361; 0365

56
[ 757978-19-1 ]
2-(oxetan-3-yloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile [ No CAS ]
5-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(oxetan-3-yloxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 80℃; for 18h; Inert atmosphere;	14 [0390] A suspension, kept under nitrogen, of 4.63 g (10.0 mmol) of 1-(benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine, 3.31 g (11.0 mmol) of 2-(oxetan-3-yloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile and 1.01 g (12.0 mmol) of sodium hydrogencarbonate in 20 ml of DMF and 10 ml of water is warmed to 80° C. with stirring. 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II) chloride are then added. The reaction mixture is stirred at 80° C. for 18 hours. The reaction mixture is cooled to room temperature, and water is added. The precipitate formed is filtered off with suction, washed with water and dried in vacuo. The crude product is crystallised from isopropanol: 5-(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(oxetan-3-yloxy)benzonitrile as pale-grey powder; HPLC/MS (A): 3.14 min, [M+H] 510/512.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2014/323481, 2014, A1 Location in patent: Paragraph 0386; 0390

57
[ 214210-21-6 ]
[ 757978-19-1 ]
5-[1-(benzenesulfonyl)-5-bromo-pyrrolo[2,3-b]pyridin-3-yl]-2-fluorobenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate; In water; N,N-dimethyl-formamide; at 40 - 80℃;Inert atmosphere;	A suspension, kept under nitrogen, of 4.63 g (10.0 mmol) of 1-(benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine, 1.81 g (11.0 mmol) of <strong>[214210-21-6](3-cyano-4-fluorophenyl)boronic acid</strong> and 1.01 g (12.0 mmol) of sodium hydrogencarbonate in 20 ml of DMF and 10 ml of water is warmed to 40 C. with stirring. 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II) chloride are then added. The reaction mixture is heated to 80 C. and stirred at this temperature for 18 hours. The reaction mixture is cooled to room temperature, and water is added. The precipitate formed is filtered off with suction, washed with water and dried in vacuo: 5-[1-(benzenesulfonyl)-5-bromo-pyrrolo[2,3-b]pyridin-3-yl]-2-fluorobenzonitrile as pale-brown powder; HPLC/MS (B): 2.77 min, [M+H] 456/458.

Reference： [1]Patent: US2014/323481,2014,A1 .Location in patent: Paragraph 0339-0340

58
[ 757978-19-1 ]
[ 1292317-54-4 ]
5-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(tetrahydro-2H-pyran-4-yloxy)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With trans-bis(triphenylphosphine)palladium dichloride; sodium hydrogencarbonate In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	6 5-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(tetrahydro-2H-pyran-4-yloxy) benzonitrile 5-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-(tetrahydro-2H-pyran-4-yloxy) benzonitrile (0254) To a solution of 2-(oxan-4-yloxy)-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (7.8 g, 23.75 mmol) and 1-(benzenesulfonyl)-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (10.0 g, 21.59 mmol) in N,N-dimethylformamide (300 mL) were added sodium bicarbonate (1.8 g, 21.55 mmol) and Pd(PPh3)2Cl2 (303 mg, 0.43 mmol) at room temperature. The resulting mixture was stirred for 2 h at 80° C. The reaction mixture was cooled to room temperature and quenched by the addition of water (100 mL). The resulting mixture was extracted with ethyl acetate (200 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 100% gradient) to yield 5-[1-(benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl]-2-(oxan-4-yloxy)benzonitrile as a off-white solid (8 g, 69%). MS: m/z=538.0 [M+H]+.
	With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In water; N,N-dimethyl-formamide at 40 - 80℃; Inert atmosphere;	3 EXAMPLE 3 A suspension, kept under nitrogen, of 4.63 g (10.0 mmol) of 1-(benzenesulfonyl)-5-bromo-3-iodopyrrolo[2,3-b]pyridine, 3.62 g (11.0 mmol) of 2-tetrahydropyran-4-yloxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzonitrile and 1.01 g (12.0 mmol) of sodium hydrogencarbonate in 20 ml of DMF and 10 ml of water is warmed to 40° C. with stirring. 140 mg (0.20 mmol) of bis(triphenylphosphine)palladium(II) chloride are then added. The reaction mixture is heated to 80° C. and stirred at this temperature for 18 hours. The reaction mixture is cooled to room temperature, and water is added. The precipitate formed is filtered off with suction, washed with water and dried in vacuo: 5-[1-(benzenesulfonyl)-5-bromopyrrolo-[2,3-b]pyridin-3-yl]-2-tetrahydropyran-4-yloxybenzonitrile as pale-grey crystals; HPLC/MS (A): 3.32 min, [M+H] 538/540; 1H NMR (400 MHz, DMSO-d6) δ [ppm]=8.57 (d, J=2.1, 1H), 8.53 (d, J=2.1, 1H), 8.37 (s, 1H), 8.19 (d, J=2.3, 1H), 8.16 (d, J=7.3, 2H), 8.05 (dd, J=8.8, 2.4, 1H), 7.75 (m, 1H), 7.65 (t, J=7.8, 2H), 7.44 (d, J=9.0, 1H), 4.90 (dt, J=11.7, 3.9, 1H), 3.88 (m, 2H), 3.56 (ddd, J=11.4, 8.2, 3.2, 3H), 2.03 (m, 2H), 1.69 (dtd, J=12.1, 8.1, 3.8, 2H).

Reference： [1]Current Patent Assignee: MERCK KGAA - US2016/376283, 2016, A1 Location in patent: Paragraph 0252; 0254
[2]Current Patent Assignee: MERCK KGAA - US2014/323481, 2014, A1 Location in patent: Paragraph 0308-0310

59
[ 757978-19-1 ]
[ 1196662-25-5 ]
{5-[(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)hydroxymethyl]-6-fluoro-pyridin-2-yl}(4-methoxybenzyl)carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.155 g	Stage #1: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine With isopropylmagnesium chloride In tetrahydrofuran at -50 - 5℃; for 1.16667h; Inert atmosphere; Stage #2: (6-fluoro-5-formylpyridin-2-yl)(4-methoxybenzyl)carbamic acid tert-butyl ester In tetrahydrofuran at -45 - 20℃; Inert atmosphere;	23.1 Step 1-Preparation of {5-[(1-benzenesulfonyl-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-6-fluoro-pyridin-2-yl}-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (166) To a solution of 1-benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine (165, 1.00 g, 2.16 mmol) in 7 mL of tetrahydrofuran at -50° C. under nitrogen, isopropylmagnesium chloride (1.18 mL, 2.35 mmol) was added slowly. The reaction was warmed to 5° C. over 70 minutes, then cooled to -45° C. and (6-fluoro-5-formyl-pyridin-2-yl)-(4-methoxy-benzyl)-carbamic acid tert-butyl ester (83, 0.678 g, 1.88 mmol) in 3.0 mL of tetrahydrofuran was added. The reaction was allowed to warm to room temperature over 2-3 hours. The reaction was mixed with aqueous 1 N citric acid and extracted with ethyl acetate. The organic layer was washed with water and brine, then dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with ethyl acetate and hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound as a white solid (166, 1.155 g). MS (ESI) [M+H]+=696.4 and 698.3.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US9096593, 2015, B2 Location in patent: Page/Page column 389; 390; 393

60
[ 757978-19-1 ]
[ 98-80-6 ]
[ 1377503-74-6 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; sodium hydroxide for 2h; Inert atmosphere; Reflux;	8.2 2: Preparation of 3-pyrid-4-yl-5-bromo-1H-pyrrolo(2,3-b)pyridine (B9) N2 protection,(3.0 mL), 5-bromo-3-iodo-1- (phenylsulfonyl) benzenesulfonyl chlorideYl) -1H-pyrrole [2,3-b] pyridine (B8) (100.0 mg, 0.22 mmol)Pyridine boronic acid (N1) (27.0 mg, 0.22 mmol), Pd (PPh3) 4 (10.1 mg, 8.8x10-3 mmol), K2CO3 (90.0 mg, 660 mmol)After refluxing reaction in oil bath for 1.5 h,Add 6N NaOH solution, continue the reaction 0.5h,The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to remove the solvent. The product was purified by silica gel column chromatography (eluent), eluted with water and dried over anhydrous sodium sulfate Purification on silica gel gave 3-pyridyl-5-bromo-lH-pyrrole (2,3-b) pyridine as a solid product (B9).

Reference： [1]Current Patent Assignee: FUDAN UNIVERSITY - CN106117181, 2016, A Location in patent: Paragraph 0149; 0150; 0151

61
[ 757978-19-1 ]
1-[(ethyl(methyl)sulfamoyl)amino]-2,4-difluoro-3-formylbenzene [ No CAS ]
1-(benzenesulfonyl)-5-bromo-3-[[3-[[ethyl(methyl)sulfamoyl]amino]-2,6-difluorophenyl]hydroxymethyl]pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65.4%	Stage #1: 1-[(ethyl(methyl)sulfamoyl)amino]-2,4-difluoro-3-formylbenzene With 2-mesitylmagnesium bromide In tetrahydrofuran at -78℃; for 0.666667h; Inert atmosphere; Stage #2: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine With isopropylmagnesium chloride In tetrahydrofuran at -40 - 20℃; for 1h; Inert atmosphere;	3.1; 3.2 Synthesis of 1-(benzenesulfonyl)-5-bromo-3-[[3-[[ethyl(methyl)sulfamoyl]amino]-2,6-difluoro-phenyl]-hydroxy-methyl]pyrrolo[2,3-b]pyridine (13) Step 1: To a solution of 1-[[ethyl(methyl)sulfamoyl]amino]-2,4-difluoro-3-formyl-benzene (11, 0.76 g, 2.73 mmol) in THF (5 mL), under nitrogen at -78° C., was added 1M mesitylmagnesium bromide in THF (2.8 ml). The reaction solution was stirred for 40 minutes. Step 2: To 1-(benzenesulfonyl)-5-bromo-3-iodo-pyrrolo[2,3-b]pyridine (17, 1.76 g, 3.79 mmol) in THF (10 mL), under an atmosphere of nitrogen at -40° C., was added a solution of i-PrMgCl (2.0 M in THF, 1.9 mL). The reaction mixture was allowed to warm up to 5° C. in 1 hour. The reaction mixture was cooled to -40° C. and added the reaction solution from step 1. The resulting reaction mixture was allowed to warm to room temperature in 1 hr, poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, concentrated and purified by silica gel column chromatography using 20% to 100% ethyl acetate in hexane as an eluent to give the desired product (13, 1.10 g, 65.4%). MS (ESI) [M+H+]+=614.7 and 616.7. 1H NMR spectrum is consistent with the structure of the compound.

Reference： [1]Current Patent Assignee: DAIICHI SANKYO COMPANY, LIMITED - US2017/157120, 2017, A1 Location in patent: Paragraph 0461-0462

62
[ 757978-19-1 ]
N-(2-chloro-5-(3-(pyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 80 °C / Inert atmosphere 1.2: 0.5 h / 80 °C 2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 1.5 h / 100 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 2 steps 1.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; water / 50 °C / Inert atmosphere 1.2: 80 °C 2.1: palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate / 1,4-dioxane; water / 12 h / 100 °C / Inert atmosphere

Reference： [1]Yang, Chengbin; Zhang, Xi; Wang, Yi; Yang, Yongtai; Liu, Xiaofeng; Deng, Mingli; Jia, Yu; Ling, Yun; Meng, Ling-Hua; Zhou, Yaming [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 8, p. 875 - 880]
[2]Yang, Chengbin; Lu, Mingzhu; Chen, Yi; Xiang, Ruiqing; Qiu, Tianze; Jia, Yu; Yang, Yongtai; Liu, Xiaofeng; Deng, Mingli; Ling, Yun; Zhou, Yaming [Bioorganic Chemistry, 2021, vol. 117]

63
[ 757978-19-1 ]
[ 1692-15-5 ]
[ 1377503-74-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine; 4-pyridylboronic acid With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane; water at 80℃; for 0.5h;

Reference： [1]Yang, Chengbin; Zhang, Xi; Wang, Yi; Yang, Yongtai; Liu, Xiaofeng; Deng, Mingli; Jia, Yu; Ling, Yun; Meng, Ling-Hua; Zhou, Yaming [ACS Medicinal Chemistry Letters, 2017, vol. 8, # 8, p. 875 - 880]

64
[ 191089-06-2 ]
[ 757978-19-1 ]
C₂₁H₁₅BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 105℃; for 72h;

Reference： [1]Price, Daniel J.; Drewry, David H.; Schaller, Lee T.; Thompson, Brian D.; Reid, Paul R.; Maloney, Patrick R.; Liang, Xi; Banker, Periette; Buckholz, Richard G.; Selley, Paula K.; McDonald, Octerloney B.; Smith, Jeffery L.; Shearer, Todd W.; Cox, Richard F.; Williams, Shawn P.; Reid, Robert A.; Tacconi, Stefano; Faggioni, Federico; Piubelli, Chiara; Sartori, Ilaria; Tessari, Michela; Wang, Tony Y. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1958 - 1963]

65
[ 757978-19-1 ]
[ 99768-12-4 ]
C₂₁H₁₅BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 105℃; for 72h;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Price, Daniel J.; Drewry, David H.; Schaller, Lee T.; Thompson, Brian D.; Reid, Paul R.; Maloney, Patrick R.; Liang, Xi; Banker, Periette; Buckholz, Richard G.; Selley, Paula K.; McDonald, Octerloney B.; Smith, Jeffery L.; Shearer, Todd W.; Cox, Richard F.; Williams, Shawn P.; Reid, Robert A.; Tacconi, Stefano; Faggioni, Federico; Piubelli, Chiara; Sartori, Ilaria; Tessari, Michela; Wang, Tony Y. [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 10, p. 1958 - 1963]
[2]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

66
[ 757978-19-1 ]
dimethyl-[4-(3-phenylethynyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: copper(l) iodide; triethylamine / bis-triphenylphosphine-palladium(II) chloride / 1 h / 80 °C 2: sodium carbonate; lithium chloride / bis-triphenylphosphine-palladium(II) chloride / ethanol; toluene / 2.75 h / 105 °C 3: sodium hydroxide; water / ethanol / 1 h / 90 °C

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2004/101565, 2004, A2

67
[ 757978-19-1 ]
[4-(1-benzenesulfonyl-3-phenylethynyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-phenyl]-dimethyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: copper(l) iodide; triethylamine / bis-triphenylphosphine-palladium(II) chloride / 1 h / 80 °C 2: sodium carbonate; lithium chloride / bis-triphenylphosphine-palladium(II) chloride / ethanol; toluene / 2.75 h / 105 °C

Reference： [1]Current Patent Assignee: EISAI CO LTD - WO2004/101565, 2004, A2

68
[ 757978-19-1 ]
C₂₂H₂₄BrN₃OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 2.5 h / 100 °C / Inert atmosphere 1.2: 1.5 h / 60 °C 1.3: 20 h / 130 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2.5 h / Reflux 2: potassium hydroxide / water; methanol / 1.5 h / 60 °C 3: hydrogen bromide / 24 h / Reflux 4: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN110483508, 2019, A
[2]Cui, Ying-Jie; Liu, Zhao-Peng; Shi, Xiao-Long; Yan, Ning [Cells, 2020, vol. 9, # 3]

69
[ 757978-19-1 ]
6-(5-(4-((pyridin-4-ylamino)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)quinolin-8-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 2.5 h / 100 °C / Inert atmosphere 1.2: 1.5 h / 60 °C 1.3: 20 h / 130 °C 2.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C 3.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; ethanol; toluene / 6 h / 100 °C 3.2: 0.17 h / 20 °C
	Multi-step reaction with 6 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / 1,4-dioxane; water / 2.5 h / Reflux 2: potassium hydroxide / water; methanol / 1.5 h / 60 °C 3: hydrogen bromide / 24 h / Reflux 4: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 20 °C 5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; toluene; ethanol / 6 h / 100 °C 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN110483508, 2019, A
[2]Cui, Ying-Jie; Liu, Zhao-Peng; Shi, Xiao-Long; Yan, Ning [Cells, 2020, vol. 9, # 3]

70
[ 757978-19-1 ]
8-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline [ No CAS ]
C₁₆H₁₀BrN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.8%	Stage #1: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine; 8-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 2.5h; Inert atmosphere; Stage #2: With methanol; potassium hydroxide at 60℃; for 1.5h; Stage #3: With hydrogen bromide at 130℃; for 20h;	1.1 Example 1: Synthesis of a compound of formula I. (1) Compound 1 (5.56 g, 12 mmol) and Compound 2 (4.11 g, 14.4 mmol)Soluble in dioxane (16mL) and water (0.8mL),Add Pd (dppf) Cl2 (0.35g, 0.48mmol),And K2CO3 (4.38 g, 36 mmol) under a nitrogen atmosphere, the reaction was stirred at 100 ° C for 2.5 h.Filter while hot and concentrate under reduced pressure. A small amount of water was added to the residue, and extracted with dichloromethane.The organic phases were combined, washed with water, saturated brine, and dried over anhydrous sodium sulfate. filter,Concentrated under reduced pressure to obtain a crude off-white solid.The above crude product was dissolved in 60 mL of methanol,20 mL of potassium hydroxide (6.8 g, 120 mmol) was added, and the reaction was stirred at 60 ° C for 1.5 h.Cool to room temperature, adjust the pH to neutral with saturated potassium hydrogen sulfate solution, and extract with ethyl acetate.The organic phases were combined, washed with water, saturated brine, and dried over anhydrous sodium sulfate. filter,Concentrated under reduced pressure to give a crude yellow solid.The above yellow crude product was dissolved in 20 mL of 40% hydrobromic acid, and reacted at 130 ° C. under reflux for 20 h.After cooling to room temperature, the pH was adjusted to neutral with a saturated potassium hydroxide solution, and the mixture was extracted with ethyl acetate.The organic phases were combined, washed with water, saturated brine, and dried over anhydrous sodium sulfate. Filtration, concentration under reduced pressure, and silica gel column chromatography (dichloromethane: methanol = 80: 1, 30: 1) gave compound 3,1.3 g of pink solid, 47.8% yield.

Reference： [1]Current Patent Assignee: SHANDONG UNIVERSITY - CN110483508, 2019, A Location in patent: Paragraph 0069-0072

71
[ 757978-19-1 ]
[ 212127-83-8 ]
C₂₂H₂₂BrN₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 1.5h; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

72
[ 757978-19-1 ]
[ 505083-04-5 ]
C₂₁H₁₄BrFN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

73
[ 757978-19-1 ]
[ 99769-19-4 ]
C₂₁H₁₅BrN₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

74
[ 757978-19-1 ]
pyridin-2-ylzinc(II) bromide [ No CAS ]
C₁₈H₁₂BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 70℃; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

75
[ 757978-19-1 ]
[ 761446-44-0 ]
[ 923584-11-6 ]

Yield	Reaction Conditions	Operation in experiment
52%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;

Reference： [1]Miles, Dillon H.; Yan, Xuelei; Thomas-Tran, Rhiannon; Fournier, Jeremy; Sharif, Ehesan U.; Drew, Samuel L.; Mata, Guillaume; Lawson, Kenneth V.; Ginn, Elaine; Wong, Kent; Soni, Divyank; Dhanota, Puja; Shaqfeh, Stefan G.; Meleza, Cesar; Chen, Ada; Pham, Amber T.; Park, Timothy; Swinarski, Debbie; Banuelos, Jesus; Schindler, Ulrike; Walters, Matthew J.; Walker, Nigel P.; Zhao, Xiaoning; Young, Stephen W.; Chen, Jie; Jin, Lixia; Leleti, Manmohan Reddy; Powers, Jay P.; Jeffrey, Jenna L. [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 11, p. 2244 - 2252]

76
[ 757978-19-1 ]
N-[(2S)-2-hydroxypropyl]-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
(S)-4-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2-hydroxypropyl)-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: POTAXIAOZHOU; BEIGENE LTD. - WO2021/13083, 2021, A1 Location in patent: Paragraph 0124; 0138; 0139

77
[ 757978-19-1 ]
(R)-N-(2-hydroxypropyl)-N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
(R)-4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(2-hydroxypropyl)-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate In 1,4-dioxane; water at 50℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: POTAXIAOZHOU; BEIGENE LTD. - WO2021/13083, 2021, A1 Location in patent: Paragraph 0149; 0161; 0162

78
[ 757978-19-1 ]
(S)-N-methyl-N-((tetrahydrofuran-3-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
(S)-4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-methyl-N-((tetrahydrofuran-3-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: POTAXIAOZHOU; BEIGENE LTD. - WO2021/13083, 2021, A1 Location in patent: Paragraph 0172; 0180; 0181

79
[ 757978-19-1 ]
(R)-N-methyl-N-((tetrahydrofuran-3-yl)methyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide [ No CAS ]
(R)-4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-methyl-N-((tetrahydrofuran-3-yl)methyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: POTAXIAOZHOU; BEIGENE LTD. - WO2021/13083, 2021, A1 Location in patent: Paragraph 0190; 0198; 0199

80
[ 757978-19-1 ]
(E)-5-bromo-3-(2-cyclopropylvinyl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: 5-bromo-3-iodo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine; (1E)-2-cyclopropylvinylboranic derivative With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; water at 50℃; Inert atmosphere; Stage #2: With water; sodium hydroxide In 1,4-dioxane at 80℃;	General procedure for the synthesis of intermediates 9a-w General procedure: To a 25 mL three neck reaction bottle, compound 8 (0.4 g, 0.86 mmol, 1.0 equiv.), R5-Bpin/R5-B(OH)2 (1.05 equiv.) PdCl2(dppf) (0.031 g, 0.043 mmol), K2CO3 (0.30 g, 2.15 mmol), 1,4-dioxane (6.0 mL), and H2O (1.5 mL) were added. The reaction was purged with nitrogen and heated at 50 °C for 1.5 h, then added 6 N NaOH (2.0 mL) and heated at 80 °C for 0.5 h. After cooling to room temperature, the mixture was diluted with water and was neutralized with 6 N HCl, and was extracted with CH2Cl2 three times. The organic phase was washed with brine, dried over Na2SO4, and concentrated under vacuum and purified by silica gel column chromatography (10:1 to 4:1, Petroleum ether/EtOAc) to afford the pure product.