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Chemical Structure| 648904-83-0 Chemical Structure| 648904-83-0

Structure of 648904-83-0

Chemical Structure| 648904-83-0

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Product Details of [ 648904-83-0 ]

CAS No. :648904-83-0
Formula : C7H8BFO4S
M.W : 218.01
SMILES Code : O=S(C1=CC=C(B(O)O)C=C1F)(C)=O
MDL No. :MFCD09878323
InChI Key :RJKFNKNDTBNEST-UHFFFAOYSA-N
Pubchem ID :45933628

Safety of [ 648904-83-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Application In Synthesis of [ 648904-83-0 ]

* 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 [ 648904-83-0 ]

[ 648904-83-0 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 648905-98-0 ]
  • [ 648904-83-0 ]
  • [ 648906-12-1 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; for 3h;Heating / reflux; Dissolve 1-12- [4- (6-benzyloxy-2-bromo-benzo [b] thiophen-3-yloxy)-phenoxy]- ethyl}-piperidine (350 mg, 0.65 mmol) and 3-fluoro-4-methanesulfonyl-phenyl-boronic acid (213 mg, 0.98 mmol) in dioxane (10 mL) and add 10% aqueous sodium carbonate (9 mL) and Pd (PPh3) 4 (75 mg, 0.065 mmol). Heat to reflux for 3 hours. Partition the reaction mixture between dichloromethane (20 mL) and saturated aqueous ammonium chloride (20 mL). Wash the organic layer with brine (30 mL), dry with sodium sulfate, and concentrate in vacuo. Chromatograph the residue on a Si02 column eluting with methanol in dichloromethane (0 to 5%) to give 150 mg of the title compound contaminated with a 2-H reduced byproduct. Take the mixture on to the next step without further purification.
  • 2
  • [ 648904-46-5 ]
  • [ 648904-83-0 ]
  • [ 648904-86-3 ]
YieldReaction ConditionsOperation in experiment
72% With cesium fluoride;palladium diacetate; tricyclohexylphosphine; In acetonitrile; at 90℃; for 1h; Combine palladium (II) acetate (4.2 mg, 0.019 mmol), tricyclohexylphosphine (10 mg, 0. 036 mmol), the compound of Preparation 1 (92 mg, 0.18 mmol), cesium fluoride (201 mg, 1.33 mmol, ) 3-fluoro-4- (methanesulfonyl) phenyl boronic acid (68 mg, 0.31 mmol) and acetonitrile (10 mL). Heat to 90C for 1 hour. Cool to room temperature and dilute the solution with ethyl acetate (20 mL) and wash with saturated aqueous NaHCO3 (10 mL). Separate the layers, wash the organic layer with brine (10 mL), dry with MgS04, filter, and concentrate in vacuo. Chromatograph the residue on a Si02 column eluting with methanol in dichloromethane (2 to 4%) to give 69 mg of title compound (72%): mass spectrum (ion spray): m/z = 550.4 (M+H).
  • 3
  • [ 648904-85-2 ]
  • [ 648904-83-0 ]
YieldReaction ConditionsOperation in experiment
42% Combine 4-bromo-2-fluorothioanisole (US Patent No. 6,307, 047,2. 7 g, 12 mmol), oxone (38 g, 62 mmol) and methanol (200 mL) and stir for 12 hours. Filter through a pad of silica gel and elute with ethyl acetate (500 mL). Evaporate solvent and partition between dichloromethane (200 mL) and water (100 mL). Separate the layers, wash the organic layer with saturated aqueous NaHC03 (10 mL), brine (10 mL), dry with MgS04, filter, and concentrate in vacuo. Wash the crude solid with hexane (20 mL), ether (10 mL) and dry in vacuo to obtain 2.4 g of 4-bromo-2-fluoro-1-methanesulfonyl-benzene (78%). Combine 4-bromo-2-fluoro-1-methanesulfonyl-benzene (1.7 g, 6.7 mmol), [1, 1'- bis (diphenylphosphino) ferrocene] dichloropalladium (II) complex with dichloromethane (Pd (dppfjCl2 CH2Cl2, 164 mg, 0.20 mmol), bis (pinacolato) diboron (1.79 g, 7.0 mmol), potassium acetate (2 g, 20 mmol) and dimethylsulfoxide (DMSO, 100 mL). Heat the reaction mixture at 90C for 1 hour. Cool to room temperature and dilute with ethyl acetate (20 mL). Wash with brine (10 mL), dry with MgS04, filter, and concentrate in vacuo. Chromatograph the residue on a Si02 column eluting the material with ethyl acetate in hexane (30%) to give 1.74 g (80%) of 2- (3-fluoro-4-methanesulfonyl-phenyl)- 4,4, 5, 5-tetramethyl-[1, 3, 2] dioxaborolane. Combine 2- (3-fluoro-4-methanesulfonyl-phenyl)-4, 4,5, 5-tetramethyl- [1, 3,2] dioxaborolane (222 mg, 0.74 mmol), NaIO4 (474 mg, 2. 2 mmol), tetrahydrofuran (THF, 4 mL) and water (1 mL). Stir for 2 hours and add 2M HC1 in diethyl ether (0.2 mL). Stir another 12 hours and filter away the solid. Wash the filtrate with brine (10 mL), dry with MgS04 and evaporate the solvent. Wash the solid with hexane (2 x 10 mL) and ether (10 mL). Dry the solid under vacuum to obtain 68 mg of the title compound (42%).
  • 4
  • [ 648904-83-0 ]
  • [ 1246372-37-1 ]
  • [ 1246372-38-2 ]
YieldReaction ConditionsOperation in experiment
25% With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; water; at 120℃; for 0.583333h;Microwave irradiation; Example 1; 2-(3,4-Dimethoxy-phenyl)-5-(3-fluoro-4-methanesulfonyl-phenyl)-6-methyl- imidazo[2,1 -b][1 ,3,4]thiadiazoleTo a suspension of 2-(3,4-dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1- b][1 ,3,4]thiadiazole (0.035 g, 0.087 mmol, 1 eq) in dioxane (1.8 mL), 3-fluoro-4- (methylsulfonyl)phenylboronic acid (0.047 g, 0.217 mmol, 2.5 eq), Pd(Ph3P)2CI2 (0.006 g, 0.0087 mmol, 0.1 eq), potassium carbonate (0.06 g, 0.435 mmol, 5 eq) and water (0.8 mL) were added. The reaction mixture was subjected to MtR irradiation (12O ºC, 35 min, 200 tR), cooled to RT and concentrated. The residue was purified by silica gel chromatography (0-0.5% MeOH in DCM). Product fractions afforded an oily residue that was further purified by trituration with Et2O providing a pale yellow solid (0.02 g) and by preparative HPLC to give the pure product (0.010 g, 25%). HPLC-MS: (50-100% B in 8 min, 0.6 mlJmin): tR= 2.41 min, [M+H]+ m/z 448.1. 1H NMR (300 MHz, CDCI3) delta/ppm 8.03 (dd, J = 8.3, 7.7, 1 H), 7.81 - 7.70 (m, 2H), 7.39 (dt, J = 3.4, 2.0, 2H), 6.94 (d, J = 8.2, 1H), 3.96 (s, 3H), 3.94 (s, 3H), 3.26 (s, 3H), 2.59 (s, 3H).
  • 5
  • [ 648904-83-0 ]
  • [ 1314883-33-4 ]
  • [ 1314883-32-3 ]
  • 6
  • [ 648904-83-0 ]
  • 6-bromo-3-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-3H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]
  • 3-[1-(5-ethylpyrimidin-2-yl)piperidin-4-yl]-6-[3-fluoro-4-(methanesulfonyl)phenyl]-3H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 2h; General procedure: To a solution of 151 29a (35mg, 0.0901mmol) in 75 DMF (0.901mL) were added 78 [4-(methanesulfonyl)phenyl]boronic acid (27mg, 0.135mmol), PdCl2(dppf)·CH2Cl2 (7.36mg, 0.00901mmol) and 2M 79 Na2CO3 aqueous solution (0.135mL). After stirring at 100C for 2h, the reaction was quenched with 72 water and extracted with EtOAc. The organic layer was separated, dried over anhydrous Na2SO4, filtered, and reduced under pressure. The residue was purified by silica gel column chromatography (67-80% 73 EtOAc in CHCl3) to afford 40 30a as a colorless crystalline solid (20mg, 48% yield), which was not recrystallized. Mp 269-270C (EtOAc/CHCl3);
  • 7
  • [ 648904-83-0 ]
  • (R)-tert-butyl-1-(7-bromo-3-(2-cyano-5-fluorobenzyl)-4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-2-yl)piperidin-3-ylcarbamate [ No CAS ]
  • C31H32F2N6O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 100℃;Sealed tube; Inert atmosphere; General procedure: A mixture of 10 (1.09 g, 2.0 mmol), thiophen-3-ylboronic acid (0.31 g, 2.4 mmol), 1,1'-Bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (Pd(dppf)Cl2.DCM, 0.10 g, 0.12 mmol) and K2CO3 (0.69 g, 5.0 mmol) was in a sealed tube containing 10 mL of 1,4-dioxane and 2 mL of water heated at 100 C under an Ar2 atmosphere overnight. The reaction mixture was subsequently cooled to room temperature, poured into water (80 mL) and extracted with ethyl acetate (100 x 3 mL). The organic layer was successively washed with saturated sodium carbonate aqueous solution, water, and saturated salt solution, dried with anhydrous sodium sulfate, and filtered. The resulting filtrate was concentrated in vacuo and then purified by flash chromatography to yield compound 11a as a white solid (0.86 g, yield 78.3%).
  • 8
  • [ 648904-83-0 ]
  • tert-butyl 5-(4-((tert-butoxycarbonyl(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-6-cyano-3-iodo-1H-indazole-1-carboxylate [ No CAS ]
  • 3-(3-fluoro-4-(methylsulfonyl)phenyl)-5-(2-fluoro-6-methyl-4-((methylamino)methyl)phenyl)-1H-indazole-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A vial equipped with a magnetic stir bar was charged with tert-butyl 5-(4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-fluoro-6-methylphenyl)-6-cyano-3-iodo-1H-indazole-1-carboxylate (12.0 mg, 0.019 mmol), 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5.58 mg, 0.025 mmol), chloro(2-dicyclohexylphosphino-2',4',6'-triisopropyl-1,1'-biphenyl)[2-(2'-amino-1,1'-biphenyl)]palladium(II) (XPhos Pd G2, 2.3 mg, 3 mumol) and potassium phosphate (8 mg, 0.039 mmol). The vial was sealed, evacuated and backfilled with nitrogen (this process was repeated a total of three times). Then 1,4-dioxane (2.00 ml) was added followed by water (200.0 mul). The reaction mixture was heated to 80 C. for 2 h. After cooling to room temperature, the reaction mixture was concentrated under vacuum. The residue was treated with CH2Cl2 (1 mL) followed by TFA (1 mL). The mixture was stirred at room temperature for 15 min, and then concentrated under vacuum. The residue was purified using prep-LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% TFA, at flow rate of 60 mL/min) to afford the desired product. LCMS calculated C22H22FN6 (M+H)+: m/z=389.2; found: 389.2.
 

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