Name: 153435-80-4|3-Bromo-N,N-dimethylbenzenesulfonamide|98%
Brand: Ambeed
SKU: A434575
Price: 18.0 USD
Availability: InStock
Rating: 90 (22 reviews)

1
[ 2905-24-0 ]
[ 124-40-3 ]
[ 153435-80-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran at 20℃;
96%	With pyridine In tetrahydrofuran at 20℃; for 5h;	14.1 Step 1: Synthesis of 3-Bromo-7¥,7¥-dimethyl-bengenesulfonamide.[0271] Into a 20 mL scintillation vial were added 3-Bromobenzenesulfonyl chloride(O.SOlg, 1.179 mmol) and anhydrous pyridine (5 mL). A 2M solution of dimethylamine inTHF (1.0 mL, 2.0 mmol) was added dropwise, and the reaction mixture was stirred at rtunder Na for 5 h after which it was concentrated under vacuum. The crude residue waspartitioned between EtOAc and 1M citric acid. The layers were separated, and the organicphase was washed 3X with 1M citric acid, then treated with brine, dried (Na2SO4), filteredand concentrated. Trituration with Et2O provided 3-Bromo-A^7V-dimethyl-benzenesulfonamide as a white powder (0.297g, 96%). MS: m/z 263.9/265.9 [MH+].
95%	With pyridine at 0 - 20℃;

	In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
	In tetrahydrofuran
	With triethylamine In tetrahydrofuran; dichloromethane at 0 - 20℃; for 2h;	20.1 Step 1: Synthesis of 3-bromo-N,N-dimethylbenzenesulfonamide To a stirred solution of 3-bromobenzene-l-sulfonyl chloride (0.500 g, 1.96 mmol) in dichloromethane at 0 °C was added 2M dimethylamine in THF (1.66 mL, 3.33 mmol) and triethylamine (0.39 mL, 2.94 mmol). This was stirred at RT for 2h. The reaction mixture was poured into ice-water (20 mL), extracted into dichloromethane (2 x 20 mL). The organic phase was washed with brine solution (20 mL) and dried over anhydrous sodium sulphate, filtered and evaporated in vacuo. The crude material was purified by flash column chromatography to afford 3-bromo-N,N-dimethylbenzenesulfonamidc as an off-white solid (0.4 g, 77%); LCMS (ES) m/z calcd. for C8H10BrNO2S, 264.1; found, 265.9 (M+H); The crude material was used as such for the next step without column purification.

Reference： [1]Posner, Gary H.; Maxwell, John P.; O'Dowd, Hardwin; Krasavin, Mikhail; Xie, Suji; Shapiro, Theresa A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1361 - 1370]
[2]Current Patent Assignee: ELI LILLY & CO - WO2006/15124, 2006, A2 Location in patent: Page/Page column 93
[3]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]
[4]Procopiou, Panayiotis A.; Barrett, Victoria J.; Bevan, Nicola J.; Biggadike, Keith; Butchers, Peter R.; Coe, Diane M.; Conroy, Richard; Edney, Dean D.; Field, Rita N.; Ford, Alison J.; Guntrip, Stephen B.; Looker, Brian E.; McLay, Iain M.; Monteith, Michael J.; Morrison, Valerie S.; Mutch, Peter J.; Richards, Stephen A.; Sasse, Rosemary; Smith, Claire E. [Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2280 - 2288]
[5]Tanaka, Tomoyuki; Yajima, Nana; Kiyoshi, Tomoko; Miura, Yoshiki; Iwama, Seiji [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 1, p. 94 - 97]
[6]Current Patent Assignee: INIPHARM - WO2021/211974, 2021, A1 Location in patent: Paragraph 00196-00197

2
[ 874134-66-4 ]
[ 153435-80-4 ]
3-[1-hydroxy-3-(2-methoxymethylene-cyclohexyl)-propyl]-<i>N</i>,<i>N</i>-dimethyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
710 mg	Stage #1: 3-bromo-N,N-dimethyl-benzenesulfonamide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.166667h; Stage #2: 3-{2-[1-Methoxy-meth-(Z)-ylidene]-cyclohexyl}-propionaldehyde In tetrahydrofuran at -78 - 0℃;

Reference： [1]Posner, Gary H.; Maxwell, John P.; O'Dowd, Hardwin; Krasavin, Mikhail; Xie, Suji; Shapiro, Theresa A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1361 - 1370]

3
[ 153435-80-4 ]
[ 288571-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C 1.2: 710 mg / tetrahydrofuran / -78 - 0 °C 2.1: 483 mg / NMO; TPAP; MS 4A / CH₂Cl₂ / 4 h / 20 °C

Reference： [1]Posner, Gary H.; Maxwell, John P.; O'Dowd, Hardwin; Krasavin, Mikhail; Xie, Suji; Shapiro, Theresa A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1361 - 1370]

4
[ 153435-80-4 ]
3-((1R,6S,9R,12R)-12-Methoxy-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-9-yl)-N,N-dimethyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C 1.2: 710 mg / tetrahydrofuran / -78 - 0 °C 2.1: 483 mg / NMO; TPAP; MS 4A / CH₂Cl₂ / 4 h / 20 °C 3.1: triphenyl phosphite; ozone / CH₂Cl₂ / -78 °C 3.2: 3 percent / TMSOTf / CH₂Cl₂ / -78 °C

Reference： [1]Posner, Gary H.; Maxwell, John P.; O'Dowd, Hardwin; Krasavin, Mikhail; Xie, Suji; Shapiro, Theresa A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1361 - 1370]

5
[ 153435-80-4 ]
3-((1R,6S,9R,12S)-12-Methoxy-10,11,13-trioxa-tricyclo[7.2.2.0^1,6]tridec-9-yl)-N,N-dimethyl-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C 1.2: 710 mg / tetrahydrofuran / -78 - 0 °C 2.1: 483 mg / NMO; TPAP; MS 4A / CH₂Cl₂ / 4 h / 20 °C 3.1: triphenyl phosphite; ozone / CH₂Cl₂ / -78 °C 3.2: 3.5 percent / TMSOTf / CH₂Cl₂ / -78 °C

Reference： [1]Posner, Gary H.; Maxwell, John P.; O'Dowd, Hardwin; Krasavin, Mikhail; Xie, Suji; Shapiro, Theresa A. [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 6, p. 1361 - 1370]

6
[ 875781-21-8 ]
[ 153435-80-4 ]
C₂₇H₃₄N₄O₄SSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate In water; acetonitrile at 90℃; for 0.25h; Microwave irradiation;	14.2 Step 2: Synthesis of 3-[3-(2-Methoxy-phenyl)-lH-pyrazolo[3,4-b]pyridin-5-yl]-N,N-dimethyl-benzenesulfonamide.[0272] Into a 5 mL Personal Chemistry microwave reaction vial were added 3-(2-Methoxy-phenyl)-5-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-l-(2-trimethylsilanyl-ethoxymethyl)-lH-pyrrolo[2,3-b]pyridine (0.0496 g, 0.103 mmol), 3-Bromo-AW-dimethyl-benzenesulfonamide (0.0417 g, 0.143 mmol), 1,1'-bis(diphenylphosphino)ferrocenepalladium(ll)-dichloride dichloromethane adduct (13.9 mg,0.017 mmol), acetonitrile (1 mL) and saturated aqueous NaHCOs (1 mL). The vial wassealed, purged with Na, and irradiated in a Personal Chemistry Optimizer at 90 °C for15 min. The layers were separated, and the aqueous phase was extracted 3X with EtOAc.The combined organic phase was treated with brine, dried (NaaSC^), filtered andconcentrated. The crude product was dissolved in 5 mL of a solution consisting of 1 partHC1O4 (70%, ACS) and 20 parts glacial acetic acid, and the solution was stirred at rt for 1 h.The reaction mixture was concentrated under vacuum, and neutralized to pH 7 withsaturated NaHCOs followed by solid NaHCOs. The quenched reaction mixture waspartitioned between EtOAc and water, the layers were separated, and the aqueous phase wasextracted 2X with EtOAc. The combined organic phase was treated with brine, dried(Na2SO4), filtered and concentrated. Purification by mass-triggered LC (positive mode, ESI)through a C-18 reverse-phase column (Thomson Instrument Co. ODS-A 100A, 5 jo,, 50 x21.3 mm, eluting at 20 mL/min with acetonitrile (containing 0.1% formic acid) and water(containing 0.1% formic acid) in a 5-95% gradient afforded the title compound, whichupon lysophilization appeared as a light yellow powder (10.4 mg, 25 %). ^-NMR (500MHz, 4-DMSO) 5= 13.91 (br. s, 1H), 8.92 (d, J=2.0 Hz, 1H), 8.44(d, J=2.0 Hz, 1H), 8.12(m, 1H), 8.01(br.s, 1H), 7.76(m, 2H)5 7.67(dd, J=2.0, 7.5 Hz, 1H), 7. 45 (m,lH), 7.22(d,J=8.0 Hz, 1H), 7.09(t5 J=8.0 Hz, 1H), 3.85(s, 3H), 2.66 (s, 6H); MS: m/z 409.1 [MH+].

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/15124, 2006, A2 Location in patent: Page/Page column 93-94

7
[ 936092-52-3 ]
[ 153435-80-4 ]
N,N-dimethyl-3-{5-methyl-2-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-ylamino}-benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%	With caesium carbonate In 1,4-dioxane; N,N-dimethyl-formamide at 160℃; for 0.333333h; Microwave irradiation;	93 [0209] A suspension of intermediate 32 (0.13 g, 0.43 mmol), 3-bromo-iV,JV-dimethyl- benzenesulfonamide (0.14 g, 0.53 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), Xantphos (30 mg, 0.052 mmol) and cesium carbonate (0.33 g, 1.0 mmol) in dioxane/DMF (3/1, 4 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 °C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (30 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue triturated in a mixture of EtOAc/hexanes (1/5, 30 mL). After filtration, the title compound was obtained as an off white solid (60 mg, 29%).[0210] 1H NMR (500 MHz, DMSOd6): δ 2.17 (s, 3H), 2.23 (s, 3H), 2.44 (d, J= 5.0 Hz, 3H), 2.45-2.50 (m, 4H), 2.63 (s, 6H), 3.03 (t, J= 4.9 Hz, 4H), 6.81 (d, J= 9.1 Hz, 2H), 7.36 (d, J= 8.0 Hz, IH), 7.45 (d, J= 9.1 Hz, 2H), 7.54 (t, J= 8.0 Hz, IH), 7.84 (t, J= 1.9 Hz, IH), 7.90 (s, IH), 8.46 (br d, J= 7.8 Hz, IH), 8.57 (s, IH), 8.74 (s, IH). MS (ES+): m/z 482 (M+H)+ .

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2007/53452, 2007, A1 Location in patent: Page/Page column 122-123

8
[ 2905-24-0 ]
[ 506-59-2 ]
[ 153435-80-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine In tetrahydrofuran at 0 - 20℃;	140.1 EXAMPLE 140 3-[2-tert-Butyl-1-(tetrahydropyran-4-ylmethyl)-1H-imidazol-4-yl]-N.N-dimethylbenzenesulfonamide (Compound 140) Step 1; In THF (10 mL), dimethylamine hydrochloride (2.04 g, 25.0 mmol) and triethylamine (3.48 mL, 25.0 mmol) were dissolved, and 3-bromobenzenesulfonyl chloride (0.721 mL, 5.00 mmol) was added thereto at 0°C, and then, the mixture was stirred at room temperature for 1 hour. To the mixture, a saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give 3-bromo-N,N-dimethylbenzenesulfonamide (1.23 g, 4.66 mmol, yield: 93%). 1H-NMR (dppm, CDCl3): 7.93-7.92 (m, 1H), 7.76-7.70 (m, 2H), 7.44 (t, J = 7.9 Hz, 1H), 2.74 (s, 6H).
43%	With pyridine In dichloromethane at 0 - 20℃; for 16.5h; Schlenk technique;	3-Bromo-N,N-dimethylbenzenesulfonamide (27b) A 15 ml Schlenk tube was charged with 48.5 mg (587 μmol, 1.50 eq) dimethylamine hydrochloride, 200μL (1.96 mmol, 5.00 eq) pyridine and 4.3 mL abs. DCM. The solution was cooled to 0 °C before 100 mg(60 μL, 391 μmol, 1.00 eq) 3-bromobenzene-sulfonylchloride were added. After stirring at rt for 16.5 hTLC analysis indicated full conversion of the starting material. The mixture was diluted with 5 mL sat.NaHCO3 solution and 5 mL Et2O. The layers were separated and the aqueous layer was extracted withEt2O (2 x 5 mL). The combined organic layers were washed with NaH2PO4 solution (4 x 10 mL) andbrine (2 x 5 mL), dried over MgSO4 and concentrated under reduced pressure. As it was still pyridine inthe crude product, it was washed once more with NaH2PO4 solution (4 x 10 mL), dried and concentratedunder reduced pressure. Final purification via column chromatography (CH/EtOAc 3:1, size: 16.5 x 2.0cm, 14 g silica gel) yielded the pure product as colorless solid (44 mg, 43 %).

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - EP2090570, 2009, A1 Location in patent: Page/Page column 82
[2]Breinbauer, Rolf; Doler, Carina; Fuchs, Elisabeth; Grabner, Gernot F.; Mayer, Nicole; Melcher, Michaela-Christina; Migglautsch, Anna K.; Romauch, Matthias; Schweiger, Martina; Zechner, Rudolf; Zimmermann, Robert [Bioorganic and medicinal chemistry, 2020, vol. 28, # 16]

9
[ 1461-22-9 ]
[ 153435-80-4 ]
[ 153435-33-7 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 3-bromo-N,N-dimethyl-benzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at 0℃; for 0.5h;	140.2 Step 2 3-Bromo-N,N-dimethylbenzenesulfonamide (396 mg, 1.50 mmol) obtained in the above was dissolved in THF (5 mL), and under an argon atmosphere, a solution of n-butyl lithium in n-hexane (1.60 mol/L; 1.03 mL), 1.65 mmol) was added thereto at -78°C, and then, the mixture was stirred at -78°C for 10 minutes. To the mixture, tributyltin chloride (0.45 mL, 1.65 mmol) was added, and the mixture was stirred at 0°C for 30 minutes. Then, a saturated aqueous sodium hydrogen carbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give N,N-dimethyl-3-tributylstannylbenzenesulfonamide (503 mg, 1.06 mmol, yield: 71%). 1H-NMR (dppm, CDCl3): 7.84-7.67 (m, 2H), 7.54-7.45 (m, 2H), 2.70 (s, 6H), 1.58-1.50 (m, 6H), 1.38-1.26 (m, 6H), 1.15-1.08 (m, 6H), 0.92-0.85 (m, 9H).

Reference： [1]Current Patent Assignee: KIRIN HOLDINGS CO., LTD.; Kyowa Kirin (in: Kirin Holdings) - EP2090570, 2009, A1 Location in patent: Page/Page column 82

10
[ 452339-74-1 ]
[ 153435-80-4 ]
[ 452340-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; bis(tri-phenylphosphine)palladium(II) dichloride; triethylamine In acetonitrile at 20℃; for 17h; Inert atmosphere;

Reference： [1]Procopiou, Panayiotis A.; Barrett, Victoria J.; Bevan, Nicola J.; Biggadike, Keith; Butchers, Peter R.; Coe, Diane M.; Conroy, Richard; Edney, Dean D.; Field, Rita N.; Ford, Alison J.; Guntrip, Stephen B.; Looker, Brian E.; McLay, Iain M.; Monteith, Michael J.; Morrison, Valerie S.; Mutch, Peter J.; Richards, Stephen A.; Sasse, Rosemary; Smith, Claire E. [Journal of Medicinal Chemistry, 2009, vol. 52, # 8, p. 2280 - 2288]

11
[ 1240286-83-2 ]
[ 153435-80-4 ]
[ 1240285-86-2 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: tert-butyl (4-chloro-2-ethynylphenoxy)acetate; 3-bromo-N,N-dimethyl-benzenesulfonamide With piperidine; trans-bis(triphenylphosphine)palladium dichloride at 70℃; for 18h; Stage #2: With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃;

Reference： [1]Crosignani, Stefano; Prêtre, Adeline; Jorand-Lebrun, Catherine; Fraboulet, Gaële; Seenisamy, Jeyaprakashnarayanan; Augustine, John Kallikat; Missotten, Marc; Humbert, Yves; Cleva, Christophe; Abla, Nada; Daff, Hamina; Schott, Olivier; Schneider, Manfred; Burgat-Charvillon, Fabienne; Rivron, Delphine; Hamernig, Ingrid; Arrighi, Jean-François; Gaudet, Marilène; Zimmerli, Simone C.; Juillard, Pierre; Johnson, Zoe [Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7299 - 7317]

12
[ 153435-79-1 ]
[ 4637-24-5 ]
[ 153435-80-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	In N,N-dimethyl-formamide at 20 - 80℃; for 18h;

Reference： [1]Fairley, Gary; Hall, Catherine; Greenwood, Ryan [Synlett, 2013, vol. 24, # 5, p. 570 - 574]

13
[ 153435-80-4 ]
[ 1066-54-2 ]
N,N-dimethyl-3-trimethylsilanylethynylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 90℃; for 65h; Inert atmosphere;	a (a) N, N-Dimethyl-3-trimethylsllanylethynyl-benzenesulfonamide 1-24 To a solution of 3-bromo-N,N-dimethylbenzenesulfonamide (527 mg, 2.0 mmol) in DMF (2 mL) were added (PPh3)2PdCI2 (28 mg, 0.04 mmol, 2 mol%) and Cul (20 mg, 0.1 mmol,5 mol%). The mixture was purged with nitrogen for 5 mm prior to the addition of Et3N (1 .5 mL) and trimethylsilylacetylene (570 pL, 4.0 mmol) whereupon the reaction was then heated to 90°C for 65 h. The reaction mixture was cooled to rt, diluted with water (200 mL) and extracted with DCM (3 x 30 mL), before passing through a phase separator (Biotage) and concentrated in vacuo. Purification by column chromatography (BiotageSP1, 25 g KP-Sil column) eluting with isohexane to 10% EtOAc I isohexane afforded the title compound as an orange solid (301 mg, 1.1 mmol, 54%).

Reference： [1]Current Patent Assignee: AUSPHERIX LTD - WO2017/93544, 2017, A1 Location in patent: Page/Page column 89

14
5-chloro-3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole [ No CAS ]
[ 153435-80-4 ]
3-(5-chloro-3-methyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)-N,N-dimethylbenzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium acetate; palladium diacetate In N,N-dimethyl acetamide at 120℃; for 16h;	21.AS Preparation of 3-(5-chloro-3-methyl-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrazol-4-yl)-N,N-dimethylbenzenesulfonamide To a stirring solution of 5-chloro-3-methyl-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- pyrazole (6.00 g, 24.4 mmol) in N,N-dimethylacetamide (60.0 mL) at rt was added 3-bromo-N,N- dimethylbenzenesulfonamide (9.62 g, 36.6 mmol), KOAc (7.18 g, 73.2 mmol) and Pd(OAc)2 (1.64 g, 2.43 mmol). The resulting reaction mixture was heated to 120 °C, and stirring was continued for 16 h. The reaction mixture was diluted with ethyl acetate and filtered through a Celite pad and the filtrate was concentrated in vacuo. The crude compound was purified over silica gel, eluting with 20% ethyl acetate in hexane to afford 3-(5-chloro-3-methyl-l -((2- (trimethylsilyl)ethoxy)methyl)-lH-pyrazol-4-yl)-N,N-dimethylbenzenesulfonamide (6.00 g, 60%) as a colorless liquid.

Reference： [1]Current Patent Assignee: PHARMAXIS LTD - WO2018/157190, 2018, A1 Location in patent: Paragraph 0276

15
[ 22237-13-4 ]
[ 153435-80-4 ]
4`-ethoxy-N,N-dimethyl-(1,1`-biphenyl)-3-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride; In 1,2-dimethoxyethane; at 80℃; for 20h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was dried under vacuum, filled with nitrogen and charged consecutively with 1.00 eq bromine substrate, 1.00 eq boronic acid, 2.10 eq CsF, 0.05 eq PdCl2(dppf)*DCM and anhydrous DME (2 mL/0.15 mmol bromoarene). The suspension was degassed by vacuum/N2 cycles and stirred at 80 C. As TLC analysis or GC-MS analysis indicated full conversion of the starting material, the reaction mixture was cooled to rt and filtered through a pad of celite, which was rinsed with EtOAc and/or DCM. The solvent from the filtrate was removed under reduced pressure and final purification by column chromatography or silica gel filtration yielded the pure product.

Reference： [1]Bioorganic and medicinal chemistry,2020,vol. 28

16
[ 73183-34-3 ]
[ 153435-80-4 ]
[ 486422-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90.0℃; for 12.0h;Inert atmosphere;	To a stirred solution of 3-bromo-N,N-dimethylbenzene-l-sulfonamide (0.350 g, 1.33 mmol) and 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,3,2-dioxaborolane (0.505 g, 1.99 mmol) in 1,4-dioxane (5 mL) was added potassium acetate (0.263 g, 2.65 mmol). Then the reaction mixture was degassed under argon gas for 10 minutes. This was followed by the addition of [1,1'- Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.097 g, 0.133 mmol) and the reaction mixture was heated to 90 C for 12 hours. After completion of the reaction, the reaction mixture was poured into water (20 ml) and extracted with ethyl acetate (2 x20 ml). The organic phase was washed with water, brine solution and dried over anhydrous sodium sulfate, concentrated in vacuo to afford N, A-dimcthyl-3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenes sulfonamide as a brown solid ( 0.2 g, crude); The crude material was used as such for next step without column purification.

Reference： [1]ChemMedChem,2021,vol. 16,p. 1116 - 1125
[2]Patent: WO2021/211974,2021,A1 .Location in patent: Paragraph 00196; 00198

17
[ 153435-80-4 ]
C₂₆H₃₃N₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

18
[ 153435-80-4 ]
C₁₉H₂₂N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

19
[ 153435-80-4 ]
C₂₅H₃₀N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

20
[ 153435-80-4 ]
C₂₅H₃₂N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

21
[ 153435-80-4 ]
C₂₃H₂₈N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

22
[ 153435-80-4 ]
C₂₅H₃₂N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

23
[ 153435-80-4 ]
C₂₅H₃₀N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

24
[ 153435-80-4 ]
C₂₅H₃₂N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide 6: hydrazine hydrate / methanol / 20 °C 7: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

25
[ 153435-80-4 ]
C₁₆H₁₇N₃O₂S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

26
[ 153435-80-4 ]
C₂₀H₂₂N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

27
[ 153435-80-4 ]
C₂₀H₂₄N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

28
[ 153435-80-4 ]
C₁₈H₂₀N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

29
[ 153435-80-4 ]
C₂₀H₂₄N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

30
[ 153435-80-4 ]
C₂₀H₂₂N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 5: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

31
[ 153435-80-4 ]
C₂₄H₁₉N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

32
[ 153435-80-4 ]
C₂₅H₂₁N₃O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

33
[ 153435-80-4 ]
C₁₇H₁₉N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide 6: hydrazine hydrate / methanol / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

34
[ 153435-80-4 ]
C₂₀H₂₄N₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide 6: hydrazine hydrate / methanol / 20 °C 7: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 8: neat (no solvent) / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

35
[ 153435-80-4 ]
C₂₅H₃₁FN₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide 6: hydrazine hydrate / methanol / 20 °C 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

36
[ 153435-80-4 ]
C₂₀H₂₃FN₄O₃S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: toluene / Reflux 5: potassium carbonate / N,N-dimethyl-formamide 6: hydrazine hydrate / methanol / 20 °C 7: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 8: dichloromethane / 1 h / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

37
[ 153435-80-4 ]
C₁₆H₁₇N₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

38
[ 153435-80-4 ]
C₂₄H₃₀N₄O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium acetate / 1,4-dioxane / 80 °C / Inert atmosphere 2: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; tetrahydrofuran / 80 °C / Inert atmosphere 3: trifluoroacetic acid / 20 °C 4: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Sutherland, Mathew; Li, Alice; Kaghad, Anissa; Panagopoulos, Dimitrios; Li, Fengling; Szewczyk, Magdalena; Smil, David; Scholten, Cora; Bouché, Léa; Stellfeld, Timo; Arrowsmith, Cheryl H.; Barsyte, Dalia; Vedadi, Masoud; Hartung, Ingo V.; Steuber, Holger; Britton, Robert; Santhakumar, Vijayaratnam [ChemMedChem, 2021, vol. 16, # 7, p. 1116 - 1125]

39
[ 153435-80-4 ]
3-(6-(4-fluoro-3-hydroxyphenoxy)pyridin-2-yl)-N,N-dimethylbenzene sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 90 °C / Inert atmosphere 2: caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 1,4-dioxane / 18 h / 90 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: INIPHARM - WO2021/211974, 2021, A1

Yield	Reaction Conditions	Operation in experiment
> 99 %	With dmap; triethylamine In tetrahydrofuran at 20℃;	1.1 (1.1) Step 1: General procedure: Preferably, the reaction conditions for the amination of route a are: add a tetrahydrofuran solution of dimethylamine (2.0 equivalents) in a round-bottomed flask with a suitable capacity (the added volume makes the molar concentration of the compound of formula 13 be 1.0mol/L), to The brominated benzenesulfonyl chloride compound formula 13 (1.0 equivalent), triethylamine (1.1 equivalent) and 4-dimethylaminopyridine (0.2 equivalent) were sequentially added, and stirred at room temperature for 12 hours. The reaction was analyzed for completion by thin-layer chromatography. Then the reaction was quenched with 1M hydrochloric acid solution, the organic phase obtained after extraction three times with ethyl acetate was washed once with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by silica gel column chromatography ( The eluents are petroleum ether and ethyl acetate) to give the corresponding brominated benzenesulfonamide products Formulas 14a-f.

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CAS No. :	153435-80-4	MDL No. :	MFCD07363826
Formula :	C₈H₁₀BrNO₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RHBJVOGENJVLGT-UHFFFAOYSA-N
M.W :	264.14 g/mol	Pubchem ID :	7129845
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 153435-80-4 ]

Quality Control of [ 153435-80-4 ]

Related Doc. of [ 153435-80-4 ]

Product Details of [ 153435-80-4 ]

Safety of [ 153435-80-4 ]

Application In Synthesis of [ 153435-80-4 ]

[ 153435-80-4 ] Synthesis Path-Downstream 1~40

Related Functional Groups of
[ 153435-80-4 ]

Aryls

Bromides

Amines

Sulfamides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 153435-80-4 ]

Quality Control of [ 153435-80-4 ]

Related Doc. of [ 153435-80-4 ]

Product Details of [ 153435-80-4 ]

Safety of [ 153435-80-4 ]

Application In Synthesis of [ 153435-80-4 ]

[ 153435-80-4 ] Synthesis Path-Downstream 1~40

Related Functional Groups of [ 153435-80-4 ]

Aryls

Bromides

Amines

Sulfamides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 153435-80-4 ]