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[ CAS No. 710350-72-4 ] {[proInfo.proName]}

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Chemical Structure| 710350-72-4
Chemical Structure| 710350-72-4
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Product Details of [ 710350-72-4 ]

CAS No. :710350-72-4 MDL No. :MFCD16996247
Formula : C14H18BClO4 Boiling Point : -
Linear Structure Formula :- InChI Key :WDDNUAMATJHVNI-UHFFFAOYSA-N
M.W : 296.55 Pubchem ID :20816364
Synonyms :

Safety of [ 710350-72-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:
Hazard Statements:H302-H312-H332 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 710350-72-4 ]

* 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 [ 710350-72-4 ]

[ 710350-72-4 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 73183-34-3 ]
  • [ 107947-17-1 ]
  • [ 710350-72-4 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 95℃; for 12.0h; A mixture of <strong>[107947-17-1]3-bromo-4-chloro-benzoic acid methyl ester</strong> (3.13 g, 12.6 mmol), bis(pinacolato)diboron (4.79 g, 18.8 mmol), PdCI2(dppf)2 (0.74 g, 1.0 mmol), KOAc (3.69 g, 37.7 mmol) in DMF (50 mL) was sealed and heated at 95 0C for 12 hrs. The mixture was partitioned between ethyl acetate and water. Organic layer was separated, washed with water, brine, dried over MgSO4. After filtration and concentration, purification by silica gel chromatography eluting with ethyl acetate/hexane (1/9) gave 4-chloro-3-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)- benzoic acid methyl ester (3.5 g). NMR (DMSO-d6), delta, 8.19 (1 H, d, J = 2.1 Hz), 7.99( 1 H, dd, J = 2.1 , 8.4 Hz), 7.58(1 H, d, J = 8.4 Hz)1 3.85(3H, s), 1.31(12H, s).
  • 2
  • [ 14482-51-0 ]
  • [ 710350-72-4 ]
  • [ 1070892-46-4 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 90℃; for 12h; A mixture of <strong>[14482-51-0]2-bromo-3,5-dichloropyridine</strong> (2.72 g, 12 mmol), 4-chloro-3- (4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (1.78 g, 6 mmol)), 2N Na2CO3 (9.0 mL, 18 mmol), Pd(PPh3)4 (0.35 g, 0.3 mmol) in toluene/ethanol (30 mL/6 mL) was sealed and heated at 90 0C for 12 hrs. The mixture was concentrated and partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water and brine and was dried over MgSO4. After filtration and concentration, purification by silica gel chromatography eluting with ethyl <n="87"/>acetate/hexane(5/95) gave 4-chloro-3-(3,5-dichloro-pyridin-2-yl)-benzoic acid methyl ester (1.8 g). MS (M + H)+: 315.6, tR = 8.505 min (method 2)
  • 3
  • methyl 4-chloro-3-iodo-benzoate [ No CAS ]
  • [ 73183-34-3 ]
  • [ 710350-72-4 ]
YieldReaction ConditionsOperation in experiment
49% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 18h;Inert atmosphere; Compound 50.2. Methyl 4-chloro-3-(4,4,5,5-tetramethyl-l,3?2-dioxaboroIan-2- yl)benzoate. A mixture of methyl 4-chloro-3-iodo-benzoate (compound 50.1, 3.85 g, 13.0 mmol), bis(pinacolato)diboron (3.96 g, 15.6 mmol), Pd(dppf)Cl2*DCM (531 mg, 0.65 mmol) and potassium acetate (3.83 g, 39.0 mmol) in DMSO (40 mL) was degassed with argon and then heated to 80 C for 18 hours. The reaction mixture was cooled then diluted with ethyl acetate (200 mL) and sequentially washed with water, aqueous HC1 (1 M), saturated aqueous NaHC03, and brine, then dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-10 % EtOAc in hexanes) to yield 1.92 g (49 %) of the title compound as a white solid. NMR (400 MHz, Chloroform-d) δ 8.36 (d, J= 2.3 Hz, 1H), 8.01 (dd, J = 8.4, 2.3 Hz, 1H), 7.44 (d, J= 8.4 Hz, 1H), 3.94 (s, 3H), 1.40
49% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In dimethyl sulfoxide; at 80℃; for 18h;Inert atmosphere; Compound 50.2. Methyl 4-chloro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)benzoate. A mixture of methyl 4-chloro-3-iodo-benzoate (compound 50.1, 3.85 g, 13.0 mmol), bis(pinacolato)diboron (3.96 g, 15.6 mmol), Pd(dppf)Cl2 DCM (531 mg, 0.65 mmol) and potassium acetate (3.83 g, 39.0 mmol) in DMSO (40 mL) was degassed with argon and then heated to 80 C for 18 hours. The reaction mixture was cooled then diluted with ethyl acetate (200 mL) and sequentially washed with water, aqueous HC1 (1 M), saturated aqueous NaHC03, and brine, then dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; 0-10 % EtOAc in hexanes) to yield 1.92 g (49 %) of the title compound as a white solid. NMR (400 MHz, Chloroform-d) δ 8.36 (d, J= 2.3 Hz, 1H), 8.01 (dd, J= 8.4, 2.3 Hz, 1H), 7.44 (d, J= 8.4 Hz, 1H), 3.94 (s, 3H), 1.40 (s, 12H0
  • 4
  • [ 42860-04-8 ]
  • [ 710350-72-4 ]
  • 5
  • [ 631897-38-6 ]
  • [ 710350-72-4 ]
  • [ 1533442-80-6 ]
YieldReaction ConditionsOperation in experiment
50% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 20 - 90℃; for 18h;Inert atmosphere; Compound 50.3. Methyl 4-chloro-3-(2,4-dimethyl-lH-imidazol-5-yl)benzoate. To methyl 4-chloro-3-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (compound 50.2, 600 mg, 2.02 mmol) in dioxane (20 mL) was added 5-iodo-2,4-dimethyl-lH-imidazole (compound 5.5, 538 mg, 2.42 mmol) and Pd(dppf)Cl2*DCM (165 mg, 0.20 mmol). The mixture was degassed with argon and stirred for 10 minutes at room temperature, then an aqueous potassium carbonate solution (1M, 10 mL) was added and the mixture was stirred at 90 C for 18 h. The mixture was cooled and diluted with EtOAc, then filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (Si02; 0-100 % EtOAc in hexanes) to yield 270 mg (50 %) of the title compound as a foam, m/z (ES+) 265 (M+H)+. NMR (400 MHz, Chloroform-d) δ 8.07 (d, J = 2.2 Hz, 1H), 7.90 (dd, J= 8.4, 2.2 Hz, 1H), 7.50 (d, J= 8.4 Hz, 1H), 3.91 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H).
50% Compound 50.3. Methyl 4-chloro-3-(2,4-dimethyl-lH-imidazol-5-yl)benzoate. To methyl 4-chloro-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoate (compound 50.2, 600 mg, 2.02 mmol) in dioxane (20 mL) was added 5-iodo-2,4-dimethyl-lH- imidazole (compound 5.5, 538 mg, 2.42 mmol) and Pd(dppf)Cl2*DCM (165 mg, 0.20 mmol). The mixture was degassed with argon and stirred for 10 minutes at room temperature, then an aqueous potassium carbonate solution (1M, 10 mL) was added and the mixture was stirred at 90 C for 18 h. The mixture was cooled and diluted with EtOAc, then filtered through Celite. The filtrate was washed with brine, dried (MgS04), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography (S1O2; 0-100 % EtOAc in hexanes) to yield 270 mg (50 %) of the title compound as a foam, m/z (ES+) 265 (M+H)+. XH NMR (400 MHz, Chloroform-d) δ 8.07 (d, J= 2.2 Hz, 1H), 7.90 (dd, J= 8.4, 2.2 Hz, 1H), 7.50 (d, J= 8.4 Hz, 1H), 3.91 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H).
  • 6
  • [ 631897-38-6 ]
  • [ 710350-72-4 ]
  • [ 1533440-78-6 ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium acetate; XPhos; In 1,4-dioxane; at 110℃;Inert atmosphere; Sealed tube; General procedure: Step 1. General procedure for the preparation of pinacolbornane reagents: An oven-dried vial filled with argon was charged with Pd2dba3 (2 mol%), X-Phos (4 mol%), bis(pinacolato)diboron (3 equiv.) and KOAc (3 equiv.). I ,4-Dioxane was added, followed by the addition of the aryl chloride or bromide (0.5 M in 1 ,4-dioxane). The vial was sealed, and the reaction mixture was heated to 110C until aryl halide had been completely consumed, as determined by TLC analysis. At this point the reaction mixture was allowed to cool to room temperature. The reaction solution was then filtered through a thin pad of Celite (eluting with ethyl acetate) and the eluent was concentrated under reduced pressure. The crude material so obtained purified via flash chromatography on silica gel or utilized for Step 2m the Suzuki coupling reaction, directly and without purification.
  • 8
  • [ 710350-72-4 ]
  • [ 1070893-14-9 ]
  • 9
  • [ 710350-72-4 ]
  • [ 1070892-47-5 ]
  • 10
  • [ 710350-72-4 ]
  • [ 1070890-31-1 ]
  • 11
  • [ 710350-72-4 ]
  • [ 1070890-30-0 ]
  • 12
  • [ 42860-10-6 ]
  • [ 710350-72-4 ]
  • 13
  • [ 710350-72-4 ]
  • 6-bromo-3-(butan-2-yl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one [ No CAS ]
  • methyl 3-[3-(butan-2-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl]-4-chlorobenzoate [ No CAS ]
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