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Product Details of [ 707-60-8 ]

CAS No. :707-60-8 MDL No. :MFCD00017834
Formula : C8H10BrNO2S Boiling Point : -
Linear Structure Formula :- InChI Key :NQAUNPZZVCXYEJ-UHFFFAOYSA-N
M.W : 264.14 Pubchem ID :12818
Synonyms :

Calculated chemistry of [ 707-60-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 54.94
TPSA : 45.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.0
Log Po/w (XLOGP3) : 2.04
Log Po/w (WLOGP) : 2.78
Log Po/w (MLOGP) : 1.71
Log Po/w (SILICOS-IT) : 0.92
Consensus Log Po/w : 1.89

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.97
Solubility : 0.281 mg/ml ; 0.00107 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.621 mg/ml ; 0.00235 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.29
Solubility : 0.136 mg/ml ; 0.000515 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.1

Safety of [ 707-60-8 ]

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

Application In Synthesis of [ 707-60-8 ]

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

  • Downstream synthetic route of [ 707-60-8 ]

[ 707-60-8 ] Synthesis Path-Downstream   1~84

  • 2
  • [ 4521-31-7 ]
  • [ 707-60-8 ]
  • [ 16185-23-2 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate
  • 3
  • [ 707-60-8 ]
  • [ 147-93-3 ]
  • [ 16185-22-1 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate
  • 4
  • [ 124-40-3 ]
  • [ 98-58-8 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: dimethyl amine With triethylamine In tetrahydrofuran; dichloromethane at 0℃; Stage #2: 4-bromobenzenesulfonyl chloride In tetrahydrofuran; dichloromethane at 20℃; 21 Place dimethylamine (5.25 mL of a 2.0 M solution in THF, 10. 4 mmol), triethylamine (2.04 mL, 14.68 mmol) and dichloromethane (30 mL) in a round bottom flask. Cool this solution to 0°C, while stirring, and add a solution of 4- bromobenzenesulfonyl chloride (2.5 g, 9.78 mmol) in dichloromethane (30 mL). Add additional dichloromethane (10 mL) and stir the reaction overnight, letting it warm to ambient temperature. Concentrate the reaction in vacuo. Take up the resulting solid in ethyl acetate and filter. Evaporate the filtrate in vacuo and dry the resulting solid by vacuum to give 2.50 g of 4-bromo-N, N-dimethyl-benzenesulfonamide (97%). Place 4-bromo-N, N-dimethyl-benzenesulfonamide (1. 00 g, 3.77 mmol), bis (pinacolato) diboron (1.15 g, 4.53 mmol), PdCl2 (dppf)2 CH2C12 (97 mg, 0.13 mmol), potassium acetate (1.11 g, 11.32 mmol) and anhydrous dimethyl sulfoxide (12 mL) in a round bottom flask. Put the reaction in an oil bath and stir at 90°C for 8 hours. Cool the purple colored reaction to ambient temperature, quench with ample water and extract the resulting aqueous mixture into dichloromethane. Wash the combined extracts with water and brine; then dry (sodium sulfate) and evaporate the extracts invacuo. Putif, v the resulting solid on a flash column (silica gel; 2%-5% gradient ofEtOA-c in CH2CI2, load material in CH2C12) to provide 900 mg of the title compound (77%).
93% In tetrahydrofuran; water at 5 - 20℃; for 1.08h; 7.K Procedure K: Preparation of 4-bromo-N,N,-dimethylbenzenesulfonamide To a stirring solution of dimethylamine (12 mL, 40% w/w aqueous solution) in THF (20 mL) at 5 °C was added a solution of 4-bromobenzenesulfonyl chloride (5.00 g, 19.6 mmol) in THF (10 mL) over 5 min. Following addition, the mixture was left to stir at rt for 1 hour. The reaction mixture was then concentrated in vacuo and the resulting residue partitioned between water (25 mL) and CH2Cl2 (20 mL) and the aqueous layer extracted with further CH2Cl2 (20 mL x 2). The combined organics were dried over Na2SO4 and concentrated in vacuo to afford 4-bromo-N,N,- dimethylbenzenesulfonamide (4.83 g, 93%) as a white solid.1H-NMR (300 MHz; CDCl3) d ppm: 2.74 (6H, s), 7.64-7.73 (4H, m).
85% In tetrahydrofuran at 0 - 23℃; for 0.333333h;
35.6% With triethylamine In tetrahydrofuran at 20℃; for 1h; 5.A Example 5. Preparation of (R*)-N-((4-(N,N-dimethylsulfamoyl)phenyl)(2- methyl-2-azabicyclo[2.2.2]octan-l-yl)methyl)-2,6-dimethylbenzamide.; [222] Step A. Preparation of 4-bromo-N,N-dimethylbenzenesulfonamide from 4- bromobenzene-1-sulfonyl chloride.; A solution of 4-bromobenzene-l-sulfonyl chloride (1.278 g, 5 mmol) in tetrahydrofuran (20 mL) was sequentially treated with triethylamine (0.976 mL, 7.00 mmol) and 2.0 M dimethylamine in tetrahydrofuran (2.75 mL, 5.50 mmol). The resulting white mixture was stirred at room temperature for 1 hour and then filtered. The filtrate was concentrated, and the resulting residue was purified by flash column chromatography (SiO2, 0-100% ethyl acetate in hexanes) to afford 4-bromo-N,N-dimethylbenzenesulfonamide (0.470 g, 35.6%) as a white solid. IH NMR (300 MHz, chloroform-d) δ ppm 2.72 (s, 6 H), 7.56 - 7.75 (m, 4 H). m/z (ES+), (M+H)+ = 264.1, 266.1.
In tetrahydrofuran; water Yield given;
With triethylamine In tetrahydrofuran at 0 - 20℃; for 3h; III.1 To a stirred solution of 4-bromobenzenesulfonyl chloride (2.5 g, 10.0 mmol) in 50.0 mLTHF at O0C, was added 10.0 mL of 2M dimethylamine in THF. The reaction was stirred at rt for3h, then quenched with water. The mixture was extracted three times with ethyl acetate, washed with water, IN HCl and brine. The solution was dried over magnesium sulfate, filtered, and concentrated to yield IHA as a white solid which was used for next reaction step without purification.EI-MS m/r. 264.00 (M + H)+.
In dichloromethane at 23℃;
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 0.5h; 39 (Example 39) 3'-[2-Isopropyl-5-(6-methylpyridin-2-yl)-1H-imidazol-4-yl]-N,N-dimethyl-1, 1'-biphenyl-4-sulfonamide (Compound No. 1-451) The same reaction as in Example 38 was carried out using a dimethylamine solution (2 M in tetrahydrofuran solution, 3 mL, 6.0 mmol) instead of the 40% methylamine aqueous solution to obtain 72 mg (yield: 52%) of the title compound as a light brown amorphous form. Melting point: 93 to 96°C. 1H-NMR (500 MHz, CDCl3) δ ppm: 10.55 (1H, brs), 7.92 (1H, s), 7.82 (2H, d, J = 8.3 Hz), 7.76 (2H, d, J = 8.3 Hz), 7.68 (1H, m), 7.58 (1H, d, J = 7.8 Hz), 7.50 (1H, t, J = 7.8 Hz), 7.41 (1H, t, J = 7.8 Hz), 7.31 (1H, d, J = 7.8 Hz), 6.96 (1H, d, J = 7.8 Hz), 3.16 (1H, m), 2.74 (6H, s), 2.50 (3H, s), 1.39 (6H, d, J = 6.8 Hz). MS(ES) m/z: 461 (M + H)+.
In tetrahydrofuran at 0 - 20℃; for 1h;

YieldReaction ConditionsOperation in experiment
77%
/BRN= 3261758/;
  • 7
  • [ 707-60-8 ]
  • [ 89415-43-0 ]
  • [ 166386-44-3 ]
YieldReaction ConditionsOperation in experiment
10% With potassium phosphate In 1,4-dioxane; toluene at 90℃; for 5h; 49.a Example 49; 5-Cyano-lH-imidazole-2-carboxylic acid (3-cyclohex-l-enyl-4'- dimethylsulfamoylbiphenyl-4-yl)-amide; a) 4'-Amino-biphenyl-4-sulfonic acid dimethylamide; To a round bottom flask was added 4-bromo-N,N-dimethyl-benzenesulfonamide (as prepared in the previous step, 539 mg, 2.28 mmol), 4-aminophenylboronic acid (500 mg, 2.28 mmol), Pd(OAc)2 (51 mg, 0.22 mmol), K3PO4 (967 mg, 4.56 mmol) and 2-(dicyclohexyl- phosphino)- biphenyl (319 mg, 0.910 mmol). The flask was charged with toluene (10 mL) and dioxane (10 mL) and heated to 900C under Ar. After 5 h the reaction was concentrated in vacuo and the residue was purified by a 10-g silica gel SPE-column eluting with DCM followed by 10 % MeOH-DCM to afford 67 mg (10 %) of the title compound as a tan solid. Mass spectrum (ESI, m/z): Calcd. for C14H16N2O2S, 277.0 (M+H), found 277.1.
  • 9
  • [ 707-60-8 ]
  • [ 16185-23-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cu, K2CO3 2: LiAlH4 / diethyl ether
  • 10
  • [ 707-60-8 ]
  • [ 16185-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Cu, K2CO3 2: SOCl2 / benzene / Heating
Multi-step reaction with 3 steps 1: Cu, K2CO3 2: LiAlH4 / diethyl ether 3: SOCl2 / benzene / Heating
  • 11
  • [ 707-60-8 ]
  • [ 16185-25-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Cu, K2CO3 2: SOCl2 / benzene / Heating 3: ethanol
Multi-step reaction with 4 steps 1: Cu, K2CO3 2: LiAlH4 / diethyl ether 3: SOCl2 / benzene / Heating 4: ethanol
  • 12
  • [ 707-60-8 ]
  • [ 16185-26-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Cu, K2CO3 2: SOCl2 / benzene / Heating 3: ethanol 4: aq. KOH / ethanol
Multi-step reaction with 5 steps 1: Cu, K2CO3 2: LiAlH4 / diethyl ether 3: SOCl2 / benzene / Heating 4: ethanol 5: aq. KOH / ethanol
  • 13
  • [ 707-60-8 ]
  • [ 73183-34-3 ]
  • [ 486422-04-2 ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide; bis(pinacol)diborane With potassium acetate In dimethyl sulfoxide at 20 - 90℃; for 8h; Stage #2: With water In dimethyl sulfoxide 21 Place dimethylamine (5.25 mL of a 2.0 M solution in THF, 10. 4 mmol), triethylamine (2.04 mL, 14.68 mmol) and dichloromethane (30 mL) in a round bottom flask. Cool this solution to 0°C, while stirring, and add a solution of 4- bromobenzenesulfonyl chloride (2.5 g, 9.78 mmol) in dichloromethane (30 mL). Add additional dichloromethane (10 mL) and stir the reaction overnight, letting it warm to ambient temperature. Concentrate the reaction in vacuo. Take up the resulting solid in ethyl acetate and filter. Evaporate the filtrate in vacuo and dry the resulting solid by vacuum to give 2.50 g of 4-bromo-N, N-dimethyl-benzenesulfonamide (97%). Place 4-bromo-N, N-dimethyl-benzenesulfonamide (1. 00 g, 3.77 mmol), bis (pinacolato) diboron (1.15 g, 4.53 mmol), PdCl2 (dppf)2 CH2C12 (97 mg, 0.13 mmol), potassium acetate (1.11 g, 11.32 mmol) and anhydrous dimethyl sulfoxide (12 mL) in a round bottom flask. Put the reaction in an oil bath and stir at 90°C for 8 hours. Cool the purple colored reaction to ambient temperature, quench with ample water and extract the resulting aqueous mixture into dichloromethane. Wash the combined extracts with water and brine; then dry (sodium sulfate) and evaporate the extracts invacuo. Putif, v the resulting solid on a flash column (silica gel; 2%-5% gradient ofEtOA-c in CH2CI2, load material in CH2C12) to provide 900 mg of the title compound (77%).
68% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; for 16h; Inert atmosphere; 7.L Procedure L: Preparation of N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)benzenesulfonamide A stirring suspension of 4-bromo-N,N-dimethyl-benzenesulfonamide (1.00 g, 3.79 mmol) 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.15 g, 4.54 mmol) and potassium acetate (1.11 g, 11.4 mmol) in 1,4-dioxane (25 mL) was flushed with nitrogen for 15 min before the addition of 1,1'-bis(diphenylphosphino)ferrocene- palladium(II)dichloride dichloromethane complex (155 mg, 0.19 mmol). The resulting suspension was heated at 80 °C under nitrogen for 16 hours. The mixture was cooled to rt, partitioned between EtOAc (40 mL) and water (30 mL) and filtered through Celite. The organic layer was separated and the aqueous layer was extracted with further EtOAc (20 mL x 2). The combined organics were then washed with brine, dried (Na2SO4) and concentrated in vacuo to afford N,N-dimethyl-4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (1.60 g, 68%) as a grey solid.1H-NMR (300 MHz; CDCl3) d ppm: 1.38 (12H, s), 2.71 (6H, s), 7.77 (2H, dd, J = 8.4, 1.0 Hz), 7.98 (2H, dd, J = 8.4, 0.9 Hz).
53.8% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide Reflux; Inert atmosphere; 13 Example 13 Synthesis of N, N-dimethyl-4- (4,4,5,5-tetramethyl-1,3,2-dioxolane-2-yl) benzenesulfonamide (compound 16) N, N-dimethyl-4-bromobenzenesulfonamide (845.1mg, 3.2mmol), (BPIN) 2 (2.03g, 8.0mmol), Pd (dppf) Cl2 (263.2mg, 322.4μmol) andNa2CO3 (678.4 mg, 6.4 mmol) was dissolved in a solution of DMF / H2O (10/1, 20 mL) and heated under reflux overnight under nitrogen protection.After the reaction was completed, water (20 mL) was added, and DCM (50 mL) was added for dilution, followed by extraction with DCM (50 mL × 3). The organic layers were combined,After drying Na2SO4, the solvent was distilled off under reduced pressure, and column chromatography (EtOAC: PE 1: 3) was used to obtain compound 16.Yield: 53.8%
45% With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2h; 15.E The N,N-dimethyl-4-bromophenyl sulfonamide above (0.486 g, 1.84 mmol, 1.0 eq.), the bis(pinacolato)diboron (538.5 mg, 2.12 mmol, 1.15 eq.), potassium acetate (881.2 mg, 8.98 mmol, 4.88 eq.), and the PdC^dppf) (1 l.Omg, 0.015mmol) were weighed into a 20 mL scintillation vial. DMF (6 mL) was added, the vial was flushed with nitrogen, capped, and placed to stir in an 80 deg C aluminum block. After 2 hr, the reaction was cooled to rt, diluted with diethyl ether, and washed with water. The organic solution was dried over magnesium sulfate, filtered, and concentrated. The crude product was EPO purified by flash chromatography over silica gel (20% ethyl acetate/ hexanes) to provide the desired boronate ester 15-E-2 (256.2 mg, 45%), which was used in preparation of example 15-2 describe in below.
With potassium acetate In N,N-dimethyl-formamide at 80℃; for 2h; II.2 HB (3.21g, 0.0122mol), KOAc (3.58g, 3.0eq), HD (4.01g, 1.3eq) and PdCl2 (dppf) (0.993g, O.leq) were added in a round bottom flask. Dry DMF (60 ml) was then added under N2 protection. The resultant mixture was stirred for a while and put into an 800C oil bath. The reaction was followed by LCMS. Upon completion (2-4hrs), reaction mixture was extracted with EtOAc / water three or four times, washed with brine twice. The resultant EtOAc solution was dried with MgSO4 and concentrated to afford crude IIC. EI-MS m/r. 312 (M + H)+. Crude IIC (4.8Og, 0.0122mol), HE (3.01g, 1.3eq), Pd(PPh3)4(1.41g, O.leq), Na2CO3 (7.76g, 6.0eq), benzene (32ml), H2O (16ml) and EtOH (4ml) were mixed. The mixture was stirred and heated at 6O0C overnight. Once the mixture cooled down, in was mixture filtered. The solid was washed with water and Et2O. The organic phase was concentrated, redissolved in benzene with heating, precipitated with addition of hexane, washed with DCM and combine two batches of solid to afford Intermediate II. EI-MS m/r. 295 (M + H)+
With potassium phosphate In N,N-dimethyl-formamide at 80℃; for 3h; III.2 A mixture of IIIA (2.4 g5 9.0 mmol), bis(pinacolato)diboron (2.5 g, 10.0 mmol) and potassium phosphate (42.5 g, 20.0 mmol) in 50 mL DMF5 was purged with nitrogen gas, then added PdCl2(dppf) (4.0 g, 5.6 mmol). The solution was heated at 800C for 3h, cooled to it and quenched with water. The product was extracted three times with ethyl acetate, washed with water, saturated sodium bicarbonate and brine. The solution was dried over magnesium sulfate, filtered, concentrated then purified by silica gel column chromatography (EtO Ac-Hex 1 :1) to yield Intermediate BLI as an off-white solid. EI-MS m/z: 312.15 (M + H)+.

  • 14
  • [ 506-59-2 ]
  • [ 98-58-8 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
99% With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; 1.1 Step 1: synthesis of 4-bromo-N,N-dimethybenzenesufonamide While under nitrogen, a solution of dimethylamine hydrochloride (1.72 g. 21.1 mmol) and 4-bromobenzenesulfonyl chloride (5.14 g, 20.1 mmol) in dichloromethane was cooled to 0 °C and treated with tri ethylamine (6.29 mL, 45.3 mmol). After stirring for 2 h at room temperature, the reaction was concentrated, diluted with ethyl acetate, and washed with water. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound as a white solid 5.25 g, 99% yield. 1H NMR (400 MHz, Chloroform-d) 8 7.71 - 7.58 (m, 4H), 2.70 (s, 6H). (0236)
97% With triethylamine In dichloromethane at 5 - 20℃; for 2h; 8.1 Step 1 : To a 3L three necked flask was added lOOOmL DCM, compound 8a (200g, 0.78mol, l .Oeq) and dimethylamine hydrochloride (83g, 1.27mol, 1.02eq), to the stirred mixture was added TEA (232g, 2.3mol, 2.6eq) under 5-15 °C, then the mixture was stirred 2h at room temperature, TLC (PE: EA=10: 1, Rf=0.2) showed the reaction was complete. The mixture was poured into water, the aqueous phase extracted with DCM. The organic layer was washed with brine and dried over Na2S04, filtered and concentrated under vacuum to yield the title product 8b (200g) as a white solid, Yield: 97%.
86% With pyridine In tetrahydrofuran; dichloromethane at 0 - 20℃; 14.X Preparation of 4-bromo-N,N-dimethylbenzenesulfonamide To a stirred solution of N,N-dimethylamine hydrochloride (3.83 g, 47.0 mmol) and pyridine (8.00 mL, 98.9 mmol) in CH2C12 (16 mL) at 0 °C was added a solution of 4-bromobenzenesulfonyl chloride (4.00 g, 15.7 mmol) in CH2C12/THF (8 mL, 1 : 1). The resulting solution was stirred at 0 °C for 30 min and then allowed to warm to rt and stirred ovemight. The reaction was quenched by the addition of aq. HC1 (2 M; 25 mL) and the organics removed in vacuo. The aqueous phase was then extracted with ethyl acetate (25 mL x 2) and the combined organics then washed (water, brine), dried over Na2S04 and concentrated in vacuo to afford 4-bromo-N,N-dimethylbenzenesulfonamide (3.57 g, 86%) as an orange solid. -NMR (300 MHz; CDC13) δ ppm: 2.74 (6H, s), 7.65-7.73 (4H, m).
34% With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5.5h; 15.E 4-Bromophenylsulfonyl chloride (3.33 g, 13.0 mmol, 1.0 eq.) and dimethylamine hydrochloride (1.58g, 19.4 mmol, 1.49 eq.) were weighed into a flask. THF (25 mL) was added, followed by DIEA (5.2 mL, 29.9 mmol, 2.3 eq.). The reaction was stirred hard at rt for 5.5 h, then diluted with diethyl ether, washed with IN hydrochloric acid, then with saturated sodium bicarbonate solution. The resulting solution was dried over magnesium sulfate, filtered and concentrated to provide the crude product. The crude material was purified by recrystallization from methylene chloride:hexanes to provide the sulfonamide 15-E-l (1.1788 g, 34%).
With pyridine; hydrogenchloride In dichloromethane at 0 - 20℃; II.1 IIA (4.874g, 0.0191mmol) was added to a stirred solution of Dimethylamine hydrochloric acid (2.33Og, 1.5eq) and pyridine (8.0ml, 5.2eq) in DCM (25 ml) at 00C. After stirring for a while, the reaction mixture was allowed to warm up to rt and the reaction was followed by LCMS. Upon completion (about 3h), the mixture was extracted with Et2O / saturated NaHCC>3 aqueous solution twice, and Et2O / NaH2Pθ4 aqueous solution (pH = 3-4) twice, washed with brine twice, dried with MgSO4 and concentrated to afford HB. EI-MS m/r. 266, 264 (M + H)+
0.8 g With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; 19.1 STEP 1 : 4-BROMO-N,N-DIMETHYLBENZENESULFONAMIDE In a 100-mL round-bottomed flask, 4-bromobenzenesulfonyl chloride (1 g, 4 mmol, Sigma-Aldrich, India) was dissolved in DCM (10 mL) at rt under nitrogen atmosphere. Triethylamine (1.2 mL, 7.8 mmol, SD Fine-Chem, India) and N, N- dimethylamine hydrochloride (444 mg, 5.48 mmol, Sigma-Aldrich, India) were added sequentially to the above solution at rt under nitrogen atmosphere. The reaction mixture was stirred at rt under nitrogen atmosphere for 2 h. The reaction mixture was diluted with ice-cold water (10 mL) and DCM (20 mL) at rt. The organic layer was separated, washed with water and brine, dried over anhydrous Na2S04 and filtered. The filtrate was concentrated under reduced pressure to give 4-bromo-N,N-dimethylbenzenesulfonamide (0.8 g) as a white solid.

  • 15
  • [ 1072106-54-7 ]
  • [ 707-60-8 ]
  • [ 1072106-57-0 ]
YieldReaction ConditionsOperation in experiment
72% With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 16h;
  • 16
  • [ 1160918-11-5 ]
  • [ 707-60-8 ]
  • C25H23N5O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With palladium diacetate; triethylamine; Tri(p-tolyl)phosphine In N,N-dimethyl-formamide at 100℃;
  • 17
  • [ 38846-64-9 ]
  • [ 707-60-8 ]
  • [ 1227370-69-5 ]
YieldReaction ConditionsOperation in experiment
63% With triethylamine In acetonitrile at 80℃; for 3h; Inert atmosphere of argon; 1-1 A mixture of 4-bromo-Λ/,Λ/-dimethylbenzenesulfonamide (610 mg, 2.31 mmol) bis(triphenylphosphine)palladium(ll) chloride (Pd(PPh3)2Cl2) (33 mg, 0.05 mmol), copper (I) iodide (5 mg, 0.03 mmol) and triethylamine (3 ml_) was degassed with argon. To the above mixture was added a degassed solution of 2-ethynyl- benzaldehyde (300 mg, 2.31 mmol) in acetonitrile (3 ml_). The resulting mixture was heated at 80 °C for 3 hours under argon, and then cooled to room temperature, treated with ethyl acetate, and then washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep Flash column, 230-400 mesh, 5-40% ethyl acetate in hexane) gave 4-(2-formyl-phenylethynyl)-Λ/,Λ/-dimethyl-benzenesulfonamide (454 mg, 63%) as a brown oil. MS (ESI+) cald. for Ci7Hi5NO3S [(M+H)+] 313, obsd. 314.
  • 18
  • [ 1239322-68-9 ]
  • [ 707-60-8 ]
  • 4-((R*)-((R)-1,1-dimethylethylsulfinamido)(2-methyl-3-oxo-2-azabicyclo[2.2.2]octan-1-yl)methyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22.3% Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexanes at -78℃; Stage #2: (R)-2-methyl-N-((2-methyl-3-oxo-2-azabicyclo[2.2.2]octan-1-yl)methylene)propane-2-sulfinamide With trimethylaluminum In tetrahydrofuran; hexanes; toluene at -78℃; Stage #3: With ammonium hydroxide; ammonium chloride In tetrahydrofuran; hexanes; water; toluene 5.B Step B. Preparation of 4-((R*)-((R)-l,l-dimethylethylsulfinamido)(2- methyl-S-oxo^-azabicycloβ^^octan-l-ylJmethylJ-N^-dimethylbenzenesulfonamide from (R)-2-methyl-N-((2-methyl-3-oxo-2-azabicyclo [2.2.2] octan-1- yl)methylene)propane-2-sulfinamide.; A solution of (R^-methyl-N-^-methyl-S-oxo^-azabicycloP^^Joctan- 1 - yl)methylene)propane-2-sulfnamide (0.324 g, 1.2 mmol; prepared according to the procedures of Example 4, Steps A-B) in tetrahydrofuran (2.95 ml) at -78°C was treated with 2 M trimethylaluminum in toluene (0.648 ml, 1.30 mmol). In a separate flask, to a solution of 4-bromo-N,N-dimethylbenzenesulfonamide (0.370 g, 1.4 mmol) in tetrahydrofuran (4.01 ml) at -78 0C was added n-butyllithium (0.659 ml, 1.47 mmol) in hexanes dropwise. After 30 min, the aryl lithium solution was added rapidly dropwise in 0.5 mL portions to the solution of sulfanamide and trimethylaluminum over 5 min. After stirring for 90 min, the reaction was quenched with a mixture of 1 : 1 saturated aqueous ammonium chloride and concentrated aqueous ammonium hydroxide, and the mixture was warmed to room temperature. The mixture was extracted with ethyl acetate (x2), and the combined organic layers were washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting residue was purified by flash column chromatography (SiO2, 0- 100% ethyl acetate in hexanes) to afford 4-((R*)-((R)-l,l-dimethylethylsulfnamido)(2- methyl-3-oxo-2-azabicyclo[2.2.2]octan- 1 -yl)methyl)-N,N-dimethylbenzenesulfonamide (0.122 g, 22.3%) as a white solid. Stereochemistry : This diastereomer was arbitrarily assigned R* stereochemistry based on the stereochemical preference for addition elucidated in Example 4. IH NMR (500 MHz, chloroform-d) δ ppm 1.03 - 1.13 (m, 1 H), 1.27 (s, 9 H), 1.53 - 1.67 (m, 4 H), 1.68 - 1.77 (m, 1 H), 1.81 - 1.89 (m, 1 H), 1.93 - 2.03 (m, 1 H), 2.62 (br. s., 1 H), 2.77 (s, 6 H), 3.19 (s, 3 H), 3.85 (s, 1 H), 4.88 (s, 1 H), 7.52 (d, J=8.2 Hz, 2 H), 7.77 (d, J=8.5 Hz, 2 H). m/z (ES+), (M+H)+ = 456.3.
  • 19
  • [ 934758-28-8 ]
  • [ 707-60-8 ]
  • 6-[4-(N,N-dimethylamino-1-sulfonyl)-phenyl]-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 160℃; for 0.666667h; Microwave irradiation; Stage #2: 6-bromo-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine With sodium carbonate In 1,4-dioxane; water at 140℃; for 0.333333h; Microwave irradiation; A5 Example A5; 6-[4-(N,N-Dimethylamino-1-sulfonyl)-phenyl]-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]- oxazolo[4,5-b]pyridine; A stirred mixture of 0.13 g (0.50 mmol) 4-bromo-benzenedimethylsulfonarnide, 0.14 g (0.55 mmol) bis(pinacolato)-diboron, 8.3 mg (0.015 mmol) 1 ,1'-bis(diphenylphosphino)ferrocene (dppf), 11 mg (0.015 mmol) PdCI2(dppf)xCH2CI2 and 0.15 g (1.50 mmol) potassium acetate in 3 ml absolute dioxane is heated to 16O0C for 40 min with a microwave equipment. After cooling to room temperature 0.11 g (0.33 mmol) 6-bromo-2-[2-(4-methoxy-pyridin-2-yl)-vinyl]-oxazolo[4,5-b]pyridine (starting compound A2), 15.0 mg (0.02 mmol) PdCI2(PcHeX)3 and 1 ml of a 2 N aqueous Na2CO3 solution are added to the reaction mixture. The suspension is heated again with a microwave equipment to 14O0C for 20 min. For workup, the mixture is poured into 100 ml water and then extracted three times with CH2CI2. The combined organic phases are dried over MgSO4, filtered and concentrated in vacuo. Subsequent purification by silica gel chromatography [CH2CI2/CH3OH (98/2 parts by volume)] affords the title compound (0.17 g) as yellow crystals. The mass spectrum shows the molecular peak MH+ at 437.2 Da.
  • 20
  • [ 707-60-8 ]
  • [ 7439-95-4 ]
  • [ 1253575-22-2 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; dibromoethane, 1,2- for 1h; 236.1 EXAMPLE 236. 4-((5-(4-AMINO-6-METHYL-l,3,5-TRIAZIN-2-YL)-6-(6- METHOXYPYRIDIN-3 -YLAMINO)PYRIDIN-3 -YL)(HYDROXY)METHYL)-N,N- DIMETHYLBENZENESULFONAMIDESTEP 1 : 4-((5-(4-(BIS(4-METHOXYBENZYL)AMrNO)-6-METHYL-l,3,5-TRIAZIN-2- YL)-6-(6-METHOXYPYRIDIN-3 -YLAMINO)PYRIDΓN-3 -YL)(HYDROXY)METHYL)- N,N-DIMETHYLBENZENESULFONAMIDE[00616] A suspension of Mg turnings (49 mg) in THF (0.5 mL) was treated with 1,2- dibromoethane (25 μL) and allowed to stand for 5 min. Effervescence was observed. The suspension was the stirred and a solution of 4-bromo-N,N-dimethylbenzenesulfonamide (500 mg, 1.893 mmol) in THF (3.4 mL total volume) was added. The suspension was stirred for 1 h, after which time most of the Mg had dissolved to give about a 0.48 M solution of (4-(N5N- dimethylsulfamoyl)phenyl)magnesium bromide in THF.
  • 21
  • [ 1253571-18-4 ]
  • [ 707-60-8 ]
  • [ 1253575-20-0 ]
  • [ 1253575-19-7 ]
YieldReaction ConditionsOperation in experiment
1: 18.6% 2: 26.2% Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Stage #2: 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)nicotinaldehyde In tetrahydrofuran; hexane at -78 - 0℃; 235.1 EXAMPLE 235. 2-((5-(4-AMINO-6-METHYL-l,3,5-TRIAZLN-2-YL)-6-(6-METHOXYPYRIDIN-S-YLAMINO)PYRIDIN-S-YL)(HYDROXY)METHYL)^-BROMO-N,N-DIMETHYLBENZENESULFONAMIDESTEP 1 : 2-((5-(4-(BIS(4-METHOXYBENZYL)AMINO)-6-METHYL-l,3,5-TRIAZIN-2-YL)-6-(6-METHOXYPYRIDIN-3-YLAMINO)PYRIDIN-3-YL)(HYDROXY)METHYL)-4-BROMO-N1N-DIMETHYLBENZENESULFONAMIDE[00614] A solution of 4-bromo-N,N-dimethylbenzenesulfonamide (Aldrich; 152 mg, 0.575 mmol) in THF (1.0 mL) was cooled to -78 0C and treated dropwise with n-butyllithium (1.60 M solution in hexanes) (359 μL, 0.575 mmol). The resulting pale solution was allowed to slowly warm to 0 0C over 30 min to give a dark brown solution which was then added dropwise to a suspension of 5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-l,3,5-triazin-2-yl)-6-(6- methoxypyridin-3-ylamino)nicotinaldehyde (110.7 mg, 0.192 mmol) in THF (2.0 mL) cooled to -78 0C. The mixture was stirred for 2 h, slowly allowing to warm to 0 0C, and the resulting yellow suspension was quenched (water) and extracted into DCM from saturated aqueous NaHCθ3. The extracts were dried (MgSO4), concentrated and purified by flash chromatography (0 to 10 to 20 to 30 to 40% EtOAc in DCM) to give recovered 5-(4-(bis(4- methoxybenzyl)amino)-6-methyl-l,3,5-triazin-2-yl)-6-(6-methoxypyridin-3- ylamino)nicotinaldehyde (54.6 mg, 49%, eluting off with 20% EtOAc / DCM) followed by 2- ((5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-l,3,5-triazin-2-yl)-6-(6-methoxypyridin-3- ylamino)pyridin-3-yl)(hydroxy)methyl)-4-bromo-N,N-dimethylbenzenesulfonamide (30.0 mg, 0.036 mmol, 18.60 % yield) (eluting off with 30% EtOAc / DCM) followed by 4-((5-(4-(bis(4- methoxybenzyl)amino)-6-methyl-l,3,5-triazin-2-yl)-6-(6-methoxypyridin-3-ylamino)pyridin-3- yl)(hydroxy)methyl)-N,N-dimethylbenzenesulfonamide (38.3 mg, 0.050 mmol, 26.2 % yield) (eluting off with 40% EtOAc / DCM).
  • 22
  • [ 707-60-8 ]
  • [ 1303575-26-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrabutylammomium bromide; palladium diacetate; sodium carbonate / water / 0.08 h / 150 °C / Microwave irradiation 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / -15 - 20 °C / Inert atmosphere
  • 23
  • [ 707-60-8 ]
  • [ 1303576-89-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrabutylammomium bromide; palladium diacetate; sodium carbonate / water / 0.08 h / 150 °C / Microwave irradiation 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / -15 - 20 °C / Inert atmosphere 3: tin(II) chloride dihdyrate; thiophenol; triethylamine / acetonitrile / 0.08 h / 20 °C
  • 24
  • [ 707-60-8 ]
  • [ 1303572-01-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: tetrabutylammomium bromide; palladium diacetate; sodium carbonate / water / 0.08 h / 150 °C / Microwave irradiation 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / -15 - 20 °C / Inert atmosphere 3: tin(II) chloride dihdyrate; thiophenol; triethylamine / acetonitrile / 0.08 h / 20 °C 4: water; lithium hydroxide / tetrahydrofuran; methanol / 20 °C / Darkness
  • 25
  • [ 707-60-8 ]
  • [ 80500-27-2 ]
  • [ 1303573-58-1 ]
YieldReaction ConditionsOperation in experiment
96% With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In water; at 150℃; for 0.0833333h;Microwave irradiation; Commercially available 4-bromo-N,Ndimethylbenzenesulfonamide 13a (664 mg, 2.51 mmol) was placed in a vial together with commercially available <strong>[80500-27-2]4-methyl-3-nitrobenzeneboronic acid</strong> (500 mg, 2.77 mmol), sodium carbonate (798 mg, 7.53 mmol), Pd(OAc)2 (2.3 mg, 0.010 mmol), tetrabutylammonium bromide (809 mg, 2.51 mmol) and water (5 mL). The vial was sealed and heated under stirring at 150 C in a microwave reactor for 5 min. The reaction mixture was then diluted with water and repeatedly extracted with EtOAc. The combined organic phase was dried over anhydrous sodium sulphate and evaporated to afford a crude residue that was purified by column chromatography over silica gel using n-hexane/EtOAc mixture as the eluent.
  • 26
  • [ 707-60-8 ]
  • [ 5713-61-1 ]
  • N,N-dimethyl 4-(thiophen-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% Stage #1: thiophen-2-yl magnesium bromide With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-N,N-dimethylbenzenesulfonamide With tributylphosphine; cobalt(II) chloride In tetrahydrofuran at 20℃; Inert atmosphere; chemoselective reaction;
  • 27
  • [ 707-60-8 ]
  • [ 21970-14-9 ]
  • [ 1462903-77-0 ]
YieldReaction ConditionsOperation in experiment
68% Stage #1: pyridin-3-ylmagnesium bromide With titanium(IV) tetraethanolate In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-bromo-N,N-dimethylbenzenesulfonamide With tributylphosphine; cobalt(II) chloride In tetrahydrofuran at 60℃; Inert atmosphere; chemoselective reaction;
  • 28
  • [ 707-60-8 ]
  • [ 1572928-55-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; sodium t-butanolate / toluene / 20 - 80 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 0.42 h / 0 - 20 °C / Inert atmosphere
  • 29
  • [ 707-60-8 ]
  • [ 1572928-56-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; sodium t-butanolate / toluene / 20 - 80 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 0.42 h / 0 - 20 °C / Inert atmosphere 3: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere
  • 30
  • [ 707-60-8 ]
  • [ 1572927-81-1 ]
  • [ 1572927-80-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; sodium t-butanolate / toluene / 20 - 80 °C / Inert atmosphere 2: trifluoroacetic acid; trifluorormethanesulfonic acid / 0.42 h / 0 - 20 °C / Inert atmosphere 3: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere 4: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C
  • 31
  • [ 1361224-50-1 ]
  • [ 707-60-8 ]
  • [ 1572928-54-1 ]
YieldReaction ConditionsOperation in experiment
200 mg With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 20 - 80℃; Inert atmosphere; 19.2 STEP 2: BENZYL 4-(4-(DIMETHYLSULFAMOYL)PHENYL)-3-(l-PROPYN- 1 -YL)- 1 -PIPERAZINEC ARBOXYLATE In a 100-mL round-bottomed flask, benzyl (3S)-3-(l-propyn-l-yl)-l- piperazinecarboxylate (273 mg, 1.15 mmol, Intermediate E, Step 3) was dissolved in toluene (10 mL) at rt. The solution was degassed by purging with argon gas at rt for 30 min. BINAP (21 mg, 0.03 mmol, Sigma-Aldrich, India), Pd(OAc)2 (3 mg, 0.001 mmol, Sigma-Aldrich, India) and sodium tert-butoxide (230 mg, 2.3 mmol, Spectrochem, India) were added sequentially to the above solution at rt under argon atmosphere. The resulting mixture was homogenized by stirring at rt for 30 min and then treated with a solution of 4-bromo-N,N- dimethylbenzenesulfonamide (300 mg, 1.15 mmol) in degassed toluene (2 mL) at rt under argon atmosphere. The resulting reaction mixture was stirred overnight (12 h) at 80 °C. The reaction mixture was cooled to rt and filtered through a diatomaceous earth pad. The filtrate was diluted with cold water (30 mL) and ethyl acetate (30 mL). The organic layer was separated, washed with water and brine, dried over anhydrous Na2S04 and filtered. The filtrate was concentrated under reduced pressure and the residue obtained was purified by silica gel (60 to 120 mesh) column chromatography (eluent, 20% EtOAc- hexanes) to give benzyl 4-(4-(dimethylsulfamoyl)phenyl)-3-(l-propyn-l-yl)-l- piperazinecarboxylate (200 mg) as a white solid.
  • 32
  • [ 106-53-6 ]
  • [ 33513-42-7 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
58% With copper diacetate; Cinnamic acid; copper(l) chloride at 110℃; for 24h;
  • 33
  • 3-(3-amino-4-(benzyloxy)-1H-pyrazolo[4,3-c]pyridin-1-yl)butanenitrile [ No CAS ]
  • [ 707-60-8 ]
  • 4-((4-(benzyloxy)-1-(1-cyanopropan-2-yl)-1H-pyrazolo[4,3-c]pyridin-3-yl)amino)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-Amyl alcohol at 75℃; Sealed tube; Inert atmosphere; II-1.1 (R or S)-4-((4-(benzyloxy)-l-(l -cvanopropan-2-yl)-lH-pyrazolor4,3-c1pyridin-3- yl)amino)-N,N-dimethylbenzenesulfonamide To (R or S)-3-(3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l- yl)butanenitrile (I-108A) (40 mg, 0.13 mmol), N,N-dimethyl-4-bromophenyl sulfonamide (68.8 mg, 0.260 mmol), Pd2dba3 (30 mg, 0.033 mmol), 2-di-iert-butylphosphino-3,4,5,6-tetramethyl- 2',4',6'-triisopropyl-l , r-biphenyl (47 mg, 0.098 mmol), and potassium phosphate tribasic (55.3 mg, 0.260 mmol) in a degassed sealed microwave vial, was added i-amyl alcohol (1.74 mL) and the reaction was degassed again by successive evacuation/argon backfill (x3) prior to heating at 75°C overnight. The reaction was concentrated and purified directly by silica chromatography, eluting with 5-40% EtOAc/hexane. The product was collected and concentrated to afford the desired product, 1-la, as a light colorless solid. LRMS (ESI) calc'd for C25H27N603S [M+H]+: 491 , found 491.
  • 34
  • tert-butyl 4-(3-amino-4-(benzyloxy)-1H-pyrazolo[4,3-c]pyridine-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate [ No CAS ]
  • [ 707-60-8 ]
  • tert-butyl 4-(4-(benzyloxy)-3-((4-(N,N-dimethylsulfamoyl)phenyl)amino)-1H-pyrazolo[4,3-c]pyridin-1-yl)-4-(cyanomethyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-Amyl alcohol at 75℃; Inert atmosphere; Sealed tube; 5-1.1 fe/t-butyl 4-(4-(benzyloxy)-3-((4-(N,N-dimethylsulfamoyl)phenyl)amino)-lH- pyrazolo[4,3-clpyridin-l -yl)-4-(cyanomethyl)piperidine- 1 -carboxylate To iert-butyl 4-(3-amino-4-(benzyloxy)-lH-pyrazolo[4,3-c]pyridin-l-yl)-4- (cyanomethyl)piperidine-l -carboxylate (3.00 g, 6.49 mmol), 4-bromo-N,N- dimethylbenzenesulfonamide (3.43 g, 13.0 mmol), Pd2dba3 (0.594 g, 0.649 mmol), 2-di-tert- butylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-l, -biphenyl (0.935 g, 1.95 mmol) and potassium phosphate tribasic (2.75 g, 13.0 mmol) in a degassed sealed microwave vial, was added i-amyl alcohol (86 mL) and the reaction was degassed again by evacuation/argon backfill (x3) and heated to 75°C overnight. The reaction was concentrated and purified by silica chromatography, eluting with 10-80% EtOAc in hexanes. The desired product, 5-la, was collected and concentrated in vacuo to afford the desired product as a solid. LRMS (ESI) calc'd for C33H4oN705S [M+H]+: 646, found 646. 1H NMR (600 MHz, DMSO-J6): δ 8.53 (s, 1 H), 7.85 (d, / = 6.0 Hz, 1H), 7.68 (d, / = 9.0 Hz, 2H), 7.60 (d, / = 9.0 Hz, 2H), 7.46 (d, / = 7.8 Hz, 2H), 7.35 (m, 3H), 7.28 (m, 1H), 5.57 (s, 2H), 3.75 (d, / = 14.4 Hz, 2H), 3.28 (s, 2H), 3.03 (br s, 2H), 2.74 (d, / = 14.4 Hz, 2H), 2.47 (s, 6H), 2.03 (t, / = 10.8 Hz, 2H), 1.37 (s, 9H).
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium acetate; tert-butyl XPhos In isopropyl alcohol at 80℃; for 18h; Inert atmosphere; 1-1.1 Step 1: tertbutvl iH prazolo[4,3c1pyridin I yl)4 yanornethyl)piperidine- I -carboxylate Under nitrogen, a mixture of tert-butyi 4-[3-amino-4-.(ienzyloxy)-1H- pyrazoio[4,3-c]pidin- I -yi]-4--(cyanomethyi)piperidine- I -carboxylate (3.00 g, 6.49 mmoi), 4- bromo-N,V-dimethylhenzene- 1 -sulfonamide (3.42 g, 13.0 mmol), di-tert-huti(2,4,6- triisopropyibiphenyl-2-.yl)phosphine (1.93 g, 4.54 mmol),tris(dibenzylideneacetone)dipaliadium(0)-chloroform (1.66 g, 1.62 mmol) and potassium acetate (1,26 g, 12.9 mmoi) in 2-propanoi (70 rnL) was heated to 80°C for 18 hours. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by silica chromatography, eluting with 60% EtOAc/hexanes the title compound as a solid. LRMS (ESI) calc’d for C3,H40N;’05S [M+Hi: 647, found 647; ‘H NMR (600 MHz, DMSO-’d6): ö 8.58 (s,1H), 7.91 (d, J= 6.7 Hz, 1H), 7.73 (m, 2H), 7.68 (d, J= 9.0 Hz, 2H), 7.52 (d, J= 7.0 Hz, 2H),7,41 (t, ,J:zr 70 Hz, 3K), 7.34 (t, .1 = 7,5 Hz, IH), 5.63 (s, 2H), 3.81 (d, ,J:zr 12.6 Hz, 2H), 3.34 (s,2K), 3.09 (br 5, 2H), 2.80 (d, J= 14.0 Hz, 2H), 2.6() (s, 6H), 2.09 (m, 2H), 1.43 (s, 9H).
  • 35
  • [ 1709-59-7 ]
  • [ 707-60-8 ]
  • 36
  • [ 707-60-8 ]
  • 3'-(1,1-dicyano-3-methylbut-1-en-2-yl)-N,N-dimethyl-5'-(trifluoromethyl)-1,1’-biphenyl-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 16 h / Inert atmosphere; Heating 2: titanium tetrachloride; pyridine / chloroform; toluene / 64 h / Inert atmosphere; Sealed tube; Heating
  • 37
  • [ 707-60-8 ]
  • (±)-3'-[6-amino-5-cyano-3-methyl-4-isopropyl-2,4-dihydropyrano[2,3-c]pyrazol-4-yl]-N,N-dimethyl-5'-(trifluoromethyl)[1,1'-biphenyl]-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 16 h / Inert atmosphere; Heating 2: titanium tetrachloride; pyridine / chloroform; toluene / 64 h / Inert atmosphere; Sealed tube; Heating 3: piperidine / ethanol; 1,4-dioxane / 3.5 h / 65 °C / Inert atmosphere; Microwave irradiation
  • 38
  • [ 707-60-8 ]
  • 2-methyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)phenyl]propan-1-one [ No CAS ]
  • N,N-dimethyl-3'-(2-methylpropanoyl)-5'-(trifluoromethyl)-1,1’-biphenyl-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 16h; Inert atmosphere; Heating;
  • 39
  • [ 707-60-8 ]
  • [ 18325-52-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran at -10℃; for 0.75h; Inert atmosphere; Stage #2: With hydrogenchloride; sulfur In tetrahydrofuran; water at -20 - -10℃; for 1h; 8.2 Step 2: To a 500mL three necked flask was added 57mL isopropyl magnesium chloride in THF(2M, 0.6eq), the mixture was controlled under- 10 °C in a N2 atmosphere, n-BuLi (76mL, 0.19mol, l .Oeq) was added dropwise into the mixture, then the reaction was keeping the temperature for 15min, then compound 8b (50g, 0.19mol, 1 Oeq) in 500mL THF was added into the mixture, then the reaction was keeping the temperature for 30min, sulfur (14g, 0.23mol, 2.3eq) was added into the reaction under -20°C, then the reaction was keeping the temperature for lh, TLC (PE: EA=3 : 1, Rf =0.1) showed the reaction was complete and 400mL HCl aq. was added to the mixture under -10 °C, then white solid was precipitation, extracted with EA. The combined organic layer was concentrated under vacuum with low temperature and was purified by column chromatography on silica gel to yield the crude product 8c (1.5g), Yield: 3.6%.
  • 40
  • [ 707-60-8 ]
  • 4-(N,N-dimethylsulfamoyl)benzene-1-sulfonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: isopropylmagnesium chloride; n-butyllithium / tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere 1.2: 1 h / -20 - -10 °C 2.1: hydrogenchloride / dichloromethane; water / 0.5 h / 0 - 5 °C
  • 41
  • [ 707-60-8 ]
  • N1-[2-[4-(4-chloro-2-fluorophenyl)-1-piperazinyl] phenyl]-N4,N4-dimethylbenzene-1,4-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride; n-butyllithium / tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere 1.2: 1 h / -20 - -10 °C 2.1: hydrogenchloride / dichloromethane; water / 0.5 h / 0 - 5 °C 3.1: pyridine / tetrahydrofuran / 15 h / Reflux
  • 42
  • [ 707-60-8 ]
  • N1-[2-[4-(3-methoxyphenyl)-1-piperazinyl]phenyl]-N4,N4-dimethylbenzene-1,4-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride; n-butyllithium / tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere 1.2: 1 h / -20 - -10 °C 2.1: hydrogenchloride / dichloromethane; water / 0.5 h / 0 - 5 °C 3.1: pyridine / tetrahydrofuran / Reflux
  • 43
  • [ 707-60-8 ]
  • N1-[2-[4-(2-methoxyphenyl)-1-piperazinyl]phenyl]-N4,N4-dimethylbenzene-1,4-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride; n-butyllithium / tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere 1.2: 1 h / -20 - -10 °C 2.1: hydrogenchloride / dichloromethane; water / 0.5 h / 0 - 5 °C 3.1: pyridine / tetrahydrofuran / Reflux
  • 44
  • [ 707-60-8 ]
  • N1,N1-dimethyl-N4-[2-(4-phenyl-1-piperazinyl)phenyl]benzene-1,4-disulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride; n-butyllithium / tetrahydrofuran / 0.75 h / -10 °C / Inert atmosphere 1.2: 1 h / -20 - -10 °C 2.1: hydrogenchloride / dichloromethane; water / 0.5 h / 0 - 5 °C 3.1: pyridine / tetrahydrofuran / 60 °C
  • 45
  • [ 34176-08-4 ]
  • [ 33513-42-7 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
45% Stage #1: N,N-dimethyl-formamide With potassium <i>tert</i>-butylate In acetonitrile at 50℃; for 0.5h; Schlenk technique; Green chemistry; Stage #2: sodium 4-bromobenzenesulfinate With N-iodo-succinimide In acetonitrile at 50℃; for 12h; Schlenk technique; Green chemistry; 2. General procedure for synthesis of sulfonamides from sodium sulfinates and formamides General procedure: An oven-dried Schlenk tube equipped with a magnetic stir bar was charged with formamide 1 (2.0 mmol), KO-t-Bu (2.0 mmol) and CH3CN (2.0 mL). The mixture was stirred at 50 °C for 30 min and then a CH3CN (2.0 mL) solution containing sodium sulfinates 2 (0.5 mmol) and NIS (1.0 mmol) was slowly added dropwise. The resulting solution stirred at 50 °C for 12 h under air. The mixture was then cooled to room temperature, diluted with 30 mL of H2O, and extracted with EtOAc (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the products.
  • 46
  • [ 110-18-9 ]
  • [ 98-58-8 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
88% With calcium hydride In acetonitrile at 90℃; for 1h; Inert atmosphere; Schlenk technique; regiospecific reaction;
  • 47
  • [ 552846-17-0 ]
  • [ 707-60-8 ]
  • N,N-dimethyl-4-(1H-pyrazol-4-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With tetrakis(triphenylphosphine) palladium(0); water; caesium carbonate In 1,4-dioxane at 90℃; Inert atmosphere; 14.Y Preparation of NN-dimethyl-4-(lH-pyrazol-4-yl)benzenesulfonamide A mixture of 4-bromo-N,N-dimethyLbenzenesulfonamide (200 mg, 0.76 mmol), tert-b tyl 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)pyrazole-l-carboxylate (267 mg, 0.91 mmol) and cesium carbonate (863 mg, 2.65 mmol) in dioxane/H20 (5 mL, 4: 1) was flushed with nitrogen for 5 min before the addition of tetrakis(triphenylphosphine)palladium(0) (87.5 mg, 0.08 mmol). The resulting mixture was heated at 90 °C overnight before quenching with the addition of water (20 mL) and extraction with ethyl acetate (20 mL x 3). The organic phases were combined, dried over Na2S04 and purified by flash column chromatography, eluting with 2% methanol/CH2Cl2, to afford N,N-dimethyl-4-(lH-pyrazol-4-yl)benzenesulfonamide (140 mg, 53%) as a white solid. -NMR (300 MHz; CDC13) δ ppm: 2.76 (6H, s), 7.69 (2H, d, J 8.5 Hz), 7.83 (2H, d, J 8.4 Hz), 8.04 (2H, br. s).
  • 48
  • [ 707-60-8 ]
  • [ 100-58-3 ]
  • N,N-dimethyl-[1,1′-biphenyl]-4-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: phenylmagnesium bromide With titanium(IV) tetraethanolate; phenol In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: 4-bromo-N,N-dimethylbenzenesulfonamide With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In tetrahydrofuran; toluene at 20 - 78℃; Inert atmosphere;
  • 49
  • [ 707-60-8 ]
  • C27H25F4N5O4S [ No CAS ]
  • C28H30F4N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With pyridine-2,6-bis(carboximidamide) dihydrochloride; nickel dibromide; zinc at 100℃; for 24h; Inert atmosphere; Sealed tube;
  • 50
  • [ 707-60-8 ]
  • C18H16N4O4S [ No CAS ]
  • C19H21NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% With pyridine-2,6-bis(carboximidamide) dihydrochloride; nickel dibromide; zinc at 100℃; for 24h; Inert atmosphere; Sealed tube;
  • 51
  • [ 707-60-8 ]
  • C20H21N5O4S [ No CAS ]
  • C21H26N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With pyridine-2,6-bis(carboximidamide) dihydrochloride; nickel dibromide; zinc at 100℃; for 24h; Inert atmosphere; Sealed tube;
  • 52
  • [ 31469-22-4 ]
  • [ 707-60-8 ]
  • C11H15NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene for 0.666667h; Inert atmosphere; Stage #2: 1,1-bis(trimethylsilyloxy)prop-1-ene In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; for 12h; Sealed tube; Inert atmosphere; Further stages;
  • 53
  • [ 707-60-8 ]
  • C17H31NOSi2 [ No CAS ]
  • N-benzyl-2-(4-(N,N-dimethylsulfamoyl)phenyl)butanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27 mg Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0) In toluene for 0.666667h; Inert atmosphere; Stage #2: C17H31NOSi2 In tetrahydrofuran; N,N-dimethyl-formamide; toluene at 80℃; for 12h; Sealed tube; Inert atmosphere; Stage #3: With potassium fluoride In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene at 20℃; for 0.0833333h; Inert atmosphere;
  • 54
  • [ 707-60-8 ]
  • [ 352-13-6 ]
  • 4-(4'-fluorophenyl)-N,N-dimethylbenzene-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 4-flourophenylmagnesium bromide With titanium(IV) tetraethanolate In tetrahydrofuran; phenol at 20℃; Inert atmosphere; Stage #2: 4-bromo-N,N-dimethylbenzenesulfonamide With iron(III) chloride; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran Glovebox; Reflux; 1 Embodiment 1, 4 - (4' - fluoro phenyl) - N, N - dimethyl sulfonamide synthesis Under protection of argon, in 25 ml dry three-opening bottle Ti (OEt) added4 (91.2 Mg, 0.4 mmol) and phenol (37.7 mg, 0.4 mmol) and 3 ml tetrahydrofuran, room temperature next adds by drops 3.2 ml fluorobromobenzene using Grignard reagent (1 M in THF, 3.2 mmol), then completing continue after stirring 30 min, the prepared solution for further use. Under protection of argon, N, N - dimethyl -4 - bromobenzene sulfonamide (528 mg, 2 mmol) and 2 ml THF, stirring to dissolve, then adding FeCl3 (32.5 Mg, 0.2 mmol), TMEDA (92.8 mg, 0.8 mmol), stirring 10 minutes, the solution is dripped slowly into the prepared metal reagent, then adding 3 ml toluene, stirring reflux 6 to 8 hours to the completion of the reaction (reaction progress can be used TLC tracking). By adding 30 ml distilled water to terminate the reaction, filtering to remove the solid, solid and dichloromethane is used for repeated pulping, the filtrate CH2 Cl2 Extraction, the combined dichloromethane extract, anhydrous Na2 SO4 Drying, steaming and removing the solvent to obtain crude product, column chromatography separation to obtain the pure product 486 mg, yield is 87%.
  • 55
  • [ 87-52-5 ]
  • [ 98-58-8 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
89% With triethylamine In acetonitrile at 25℃; for 24h; 8.1-8.2 Preparation of compound 3h: (1) 1 mmol of latinosyl N, N-dimethylamino-3-methylindole shown in Formula 1, 1.5 mmol of 4-bromobenzenesulfonyl chloride as shown in Formula 2h was added to a 50 mL flask, Add 10mL of CH3CN to completely dissolve, Slowly add 1.5 mmol of Et3N, and stir the reaction at 25 ° C for 24h to obtain a reaction solution; The reaction is as follows: (2) concentrated the reaction solution under reduced pressure, Add CH2Cl2 and water, extraction, Combined organic phases, Wash with saturated saline, Dried over anhydrous sodium sulfate, The solvent was concentrated and evaporated to dryness, and then separated by silica gel column chromatography to obtain N, N-dimethylsulfonamide derivatives as shown in Formula 3h.
89% With triethylamine In acetonitrile at 25℃; for 24h; 3.2. preparation of N, N-dimethylarylsulfonamide derivatives (3a-o) General procedure: To a solution of gramine (1, 1.0mmol) and arylsulfonyl chloride (2, 1.5mmol) in dryCH3CN (10ml) at 25 C, a solution of Et3N (1.5mmol) in dry CH3CN (5ml) was addeddrop wise for 10min [20-24]. After reaction for 24 h, the reaction solution was concentratedunder reduced pressure to give crude product. The crude product was dissolvedin CH2Cl2 (15ml) and diluted with water (15ml) and extracted with CH2Cl2 (30ml 3). Subsequently, the combined organic phase was washed by saturated aq. brine(30ml), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by silica gelcolumn chromatography to obtain the target compounds in 76%-98% yields. The datafor 3a-o are shown as follows.
  • 56
  • [ 707-60-8 ]
  • 4-(6-(2,4-dione-3,4-dihydropyridin-1(2H)-yl)benzo[d]thiazol-2-yl)-N,N-dimethylmethanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; N,N-dimethyl-formamide / Reflux; Inert atmosphere 2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate / water; N,N-dimethyl-formamide / Reflux; Inert atmosphere
  • 57
  • [ 707-60-8 ]
  • [ 486422-59-7 ]
  • 58
  • [ 707-60-8 ]
  • (Z)-tert-butyl (4-((2-(4-(N,N-dimethylsulfamoyl)phenoxy)phenyl)thio)-3-fluorobut-2-en-1-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere 2.1: sodium periodate / water; tetrahydrofuran / 0.58 h / 0 - 20 °C 2.2: 1 h / 20 °C 3.1: pyridine; copper diacetate / dichloromethane / 16 h / 20 °C
  • 59
  • [ 707-60-8 ]
  • potassium trifluoro(3-(methoxycarbonyl)bicyclo[1.1.1]pentan-1-yl)boranuide [ No CAS ]
  • methyl 3-(4-(N,N-dimethylsulfamoyl)phenyl)bicyclo[1.1.1]pentane-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; tetraaqua[4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]nickel(II) chloride; sodium carbonate In 1,4-dioxane; N,N-dimethyl acetamide for 20h; Glovebox; Sealed tube; Inert atmosphere;
  • 60
  • [ 701-34-8 ]
  • [ 77-78-1 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
99% With tetrabutylammonium tetrafluoroborate; potassium carbonate In acetonitrile for 3h; Reflux;
  • 61
  • [ 707-60-8 ]
  • C23H24ClNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C 1.2: -78 - 20 °C 2.1: acetyl chloride; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
  • 62
  • [ 707-60-8 ]
  • rac-ethyl 1-(2-[4-(N,N-dimethylsulfamoyl)phenyl]bis[4-methoxyphenyl]methoxy}ethyl)piperidine-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C 1.2: -78 - 20 °C 2.1: acetyl chloride; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 20 °C / Inert atmosphere
  • 63
  • [ 707-60-8 ]
  • rac-1-(2-[4-(N,N-dimethylsulfamoyl)phenyl]bis[4-methoxyphenyl]methoxy}ethyl)piperidine-3-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 2 h / -78 °C 1.2: -78 - 20 °C 2.1: acetyl chloride; N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 3.1: potassium carbonate / acetonitrile / 16 h / 20 °C / Inert atmosphere 4.1: barium hydroxide octahydrate; water / methanol / 20 °C
  • 64
  • [ 90-96-0 ]
  • [ 707-60-8 ]
  • 4-[hydroxybis(4-methoxyphenyl)methyl]-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 2h; Stage #2: bis(p-methoxyphenyl)methanone In tetrahydrofuran; pentane at -78 - 20℃;
  • 65
  • [ 707-60-8 ]
  • [ 24388-23-6 ]
  • N,N-dimethyl-4-(2-phenyl-1,3,2λ4-oxazaborolidin-2-yl)benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -75 °C 1.2: -75 - 20 °C 2.1: acetonitrile / 20 °C
  • 66
  • [ 707-60-8 ]
  • [ 24388-23-6 ]
  • C14H16BNO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
930 mg Stage #1: 4-bromo-N,N-dimethylbenzenesulfonamide With n-butyllithium In tetrahydrofuran; hexane at -78 - -75℃; for 1h; Stage #2: 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole In tetrahydrofuran; hexane at -75 - 20℃;
  • 67
  • [ 707-60-8 ]
  • 1,2-dimethyl-4,5-dihydro-1H-imidazo[4,5-h]quinazolin-8-amine [ No CAS ]
  • 4-((1,2-dimethyl-4,5-dihydro-1H-imidazo[4,5-h]quinazolin-8-yl)amino)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In 1,4-dioxane at 140℃; for 1h; Microwave irradiation; Inert atmosphere; 2.3 Step 3: 4-((1,2-Dimethyl-4,5-dihydro-1H-imidazo[4,5-h]quinazolin-8-yl)amino)-N,N- dimethylbenzenesulfonamide A mixture of 1,2-dimethyl-4,5-dihydro-1H-imidazo[4,5-h]quinazolin-8-amine (57.8 mg, 0.269 mmol), Cs2CO3 (262 mg, 0.806 mmol), tBuBrettPhos Pd G3 (211 mg, 0.269 mmol), and 4-bromo-N,N-dimethylbenzenesulfonamide (142 mg, 0.537 mmol) in 1,4-dioxane (2 mL) was purged with nitrogen and irradiated in the microwave reactor at 140 °C for 1 hour. After cooling to room temperature, the reaction mixture was filtered, and the filtrate was concentrated. The residue was dissolved in acetonitrile and purified by prep-LCMS (Sunfire C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min) to afford 4-((1,2-dimethyl-4,5-dihydro-1H-imidazo[4,5-h]quinazolin-8-yl)amino)- N,N-dimethylbenzenesulfonamide. LCMS calculated for C19H23N6O2S (M+H)+: m/z = 399.2; Found 399.1.
  • 68
  • [ 707-60-8 ]
  • cesium 2-((1-methylcyclohexyl)oxy)-2-oxoacetate [ No CAS ]
  • [ 75927-49-0 ]
  • C17H27NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With (1,2-dimethoxyethane)dichloronickel(II); [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; sodium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine In dimethyl sulfoxide at 35℃; for 24h; Irradiation; Sealed tube; Inert atmosphere; General procedure B (GPB) for the aryl bromides: General procedure: To a flame-dried 8 mL reactionvial was charged with NiCl2•DME (0.04 mmol, 20 mol%), dtbbpy (0.04 mmol, 20mol%), Ir[dF(CF3)ppy]2(dtbbpy)PF6 (0.004 mmol, 2 mol%), aryl bromide (0.2 mmol,1.0 equiv., if solid) and Na2CO3 (0.05 mmol, 0.5 eq), cesium salt (0.4 mmol, 2.0equiv.), the vial was capped. After evacuated and backfilled nitrogen three times,DMSO [0.05 M] was added via a syringe, aryl bromide (0.2 mmol, 1.0 equiv.), ifliquid), followed by the addition of vinylborate (0.24 mmol, 1.2 equiv.). The reactionmixture was then irradiated with a 90 W blue LED lamp (at approximately 3 cm awayfrom the light source) with cooling from a fan for 24h. The reaction was quenchedwith H2O, extracted with ethyl acetate. The combined organic layers were dried withMg2SO4, filtered, and concentrated in vacuo. The crude material was purified by flashchromatography to afford the product.
  • 69
  • [ 2768-02-7 ]
  • [ 707-60-8 ]
  • [ 60472-40-4 ]
YieldReaction ConditionsOperation in experiment
81% With (1,2-dimethoxyethane)dichloronickel(II); tetrabutylammonium triphenyldifluorosilicate In N,N-dimethyl acetamide at 35℃; for 12h; Inert atmosphere; General Procedure 2 General procedure: In a nitrogen-filled glove box, aromatic halide (0.2 mmol, 1.0equiv), TBAT (270 mg, 0.5 mmol, 2.5 equiv), NiCl2(glyme) (4.4mg, 0.02 mmol, 10 mol%), and DMA (1.0 mL) were charged to an8 mL vial equipped with a magnetic stirrer bar. The vinyltrimethoxysilane(59.1 mg, 0.4 mmol, 2.0 equiv) was added. The vialwas removed from the glove box, and the reaction mixture wasstirred at rt (35 °C) for 12 h. The reaction mixture was thendiluted with EtOAc and washed with water. The organic phasewas dried over Na2SO4, filtered, and concentrated, and theresidue was purified by column chromatography on silica gel togive the product.
  • 70
  • [ 103-83-3 ]
  • [ 98-58-8 ]
  • [ 707-60-8 ]
YieldReaction ConditionsOperation in experiment
78% With calcium hydride; methyl violet In acetonitrile at 20℃; for 24h; Irradiation; Schlenk technique;
  • 71
  • [ 707-60-8 ]
  • [ 14417-01-7 ]
YieldReaction ConditionsOperation in experiment
86% With tetraethylammonium perchlorate; triethylamine In ethanol; dimethyl sulfoxide at 20℃; for 24h; Electrolysis; Green chemistry;
  • 72
  • [ 707-60-8 ]
  • tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
  • C19H28N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 73
  • [ 707-60-8 ]
  • tert-butyl 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-azabicyclo[4.1.0]heptane-3-carboxylate [ No CAS ]
  • C19H28N2O4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 74
  • [ 707-60-8 ]
  • 4,4,5,5-tetramethyl-2-(1-methylcyclopropyl)-1,3,2-dioxaborolane [ No CAS ]
  • C12H17NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 75
  • [ 1314495-37-8 ]
  • [ 707-60-8 ]
  • C17H19NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
59% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 76
  • [ 707-60-8 ]
  • 4,4,5,5-tetramethyl-2-(3-(trifluoromethyl)bicyclo[1.1.1]pentan-1-yl)-1,3,2-dioxaborolane [ No CAS ]
  • C14H16F3NO2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
54% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 77
  • [ 707-60-8 ]
  • C32H33BF3NO3 [ No CAS ]
  • C34H31F3N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% With copper(I) oxide; palladium diacetate; caesium carbonate; catacxium A at 120℃; for 24h;
  • 78
  • [ 707-60-8 ]
  • (R)-4-(1-hydroxybutyl)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (S)-5-amino-4-isobutyl-2,7-dimethyloctan-4-ol; 6,6'-di-n-butyl-2,2'-bipyridyl; nickel(II) nitrate hexahydrate; potassium fluoride; lithium iodide; diethoxymethylane / N,N-dimethyl acetamide / 20 h / 23 - 29 °C / Sealed tube 2: sodium perborate tetrahydrate / tetrahydrofuran; water / 6 h / 20 °C
  • 79
  • [ 707-60-8 ]
  • 2-(but-3-en-1-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane [ No CAS ]
  • C19H32BNO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride; nickel(II) nitrate hexahydrate; diethoxymethylane; (S)-5-amino-4-isobutyl-2,7-dimethyloctan-4-ol; 6,6'-di-n-butyl-2,2'-bipyridyl; lithium iodide In N,N-dimethyl acetamide at 23 - 29℃; for 20h; Sealed tube; enantioselective reaction; General procedure A for enantioselective NiH-catalyzed remote hydroarylation. General procedure: In a nitrogen-filled glove box, to an oven-dried 8 mL screw-cap vial equipped with a magnetic stirbar was added Ni(NO3)2·6H2O (2.3 mg, 4.0 mol %), L (1.6 mg, 3.0 mol %), (S)-L* (3.7 mg, 8.0mol %), KF (23.2 mg, 0.40 mmol, 2.0 equiv), LiI (26.8 mg, 0.20 mmol, 1.0 equiv), methyl 4-bromobenzoate (2a, 86.0 mg, 0.40 mmol, 2.0 equiv), anhydrous DMA (1.0 mL) were added (if theolefin is a solid, it was also added at this time), and the mixture was stirred for 10 min at roomtemperature, at which time 2-(but-3-en-1-yl)-4,4,6,6-tetramethyl-1,3,2-dioxaborinane (1a, 39.2 mg,0.20 mmol, 1.0 equiv) (if the aryl bromide is a liquid, it was added at this time) and DEMS (80 μL,0.50 mmol, 2.5 equiv) were added to the resulting mixture in this order. The tube was sealed witha teflon-lined screw cap, removed from the glove box and the reaction was stirred at rt (23-29 °C)for up to 20 hr (the mixture was stirred at 750 rpm, ensuring that the base was uniformly suspended).After the reaction was complete, the reaction was quenched upon the addition of H2O, and themixture was extracted with Et2O. The organic layer was concentrated to give the crude product.Dodecane (20 μL) was added as an internal standard for GC analysis. The product was purified byflash column chromatography (petroleum ether/EtOAc) for each substrate. The yields reported arethe average of at least two experiments, unless otherwise indicated.
  • 80
  • [ 707-60-8 ]
  • 3-bromo-4-(cyclopentylamino)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 12 h / 110 °C / Inert atmosphere 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 24 h / 25 °C / Inert atmosphere
  • 81
  • [ 707-60-8 ]
  • 3-bromo-4-(cyclopentyl(methyl)amino)-N,N-dimethylbenzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 12 h / 110 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 24 h / 25 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 3.2: 5 h / 60 °C / Inert atmosphere
  • 82
  • [ 707-60-8 ]
  • 2-(cyclopentyl(methyl)amino)-5-(N,N-dimethylsulfamoyl)-N-(5-ethylthiazol-2-yl)benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / toluene / 12 h / 110 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 24 h / 25 °C / Inert atmosphere 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 °C / Inert atmosphere 3.2: 5 h / 60 °C / Inert atmosphere 4.1: triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate / dimethyl sulfoxide / 12 h / 85 °C / Inert atmosphere
  • 83
  • [ 707-60-8 ]
  • [ 1003-03-8 ]
  • 4-(cycopentylamino)-N,N-dimethylbenzene-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With tris-(dibenzylideneacetone)dipalladium(0); potassium-t-butoxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 12h; Inert atmosphere; 1.2 Step 2: synthesis of 4-(cycopentyamino)-N,N-dimethybenzenesufonamide While under nitrogen, a mixture of 4-bromo-N,N-dimethylbenzene-1-sulfonamide (1.32 g, 5 mmol), (tert-butoxy)potassium (673 mg, 6 mmol), xantphos (116 mg, 0.2 mmol) and tris(dibenzylideneacetone)dipalladium(0) (92 mg, 0.1 mmol) was treated with cyclopentanamine (0.54 mL, 5.5 mmol) in toluene (5 mL) and heated to 110 °C for 12 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (20% ethyl acetate in hexanes) gives the title compound as a white solid (1.3 g, 97% yield). 1H NMR (400 MHz, Chloroform-d) 6 7.61 - 7.45 (m, 2H), 6.60 (d, J = 8.1 Hz, 2H), 3.88 - 3.69 (m, 1H), 2.70 - 2.54 (m, 6H), 2.10 - 1.94 (m, 2H), 1.83 - 1.37 (m, 6H).
  • 84
  • [ 31166-44-6 ]
  • [ 707-60-8 ]
  • [ 2771307-49-2 ]
YieldReaction ConditionsOperation in experiment
90% With tris-(dibenzylideneacetone)dipalladium(0); Cs2CO3; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 90℃; for 12h; Inert atmosphere;
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