* 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.
With (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; dichlorobis(trimethylphosphine)nickel In 1,4-dioxane at 100℃; for 12 h; Inert atmosphere; Sealed tube
Under an argon atmosphere,To the reaction vessel, 1.4 mg (0.005 mmol) of dichlorobis (trimethylphosphine) nickel,77.4 mg (0.5 mmol) of 4-chlorobenzamide,152 mg (1.0 mmol) of cesium fluoride,140 mg (0.55 mmol) of 4,4,5,5,4 ', 4', 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolanyl)180 mg (1.05 mmol) of trimethyl (2,2,2-trifluoroethoxy) silane and 0.5 mL of 1,4-dioxane were added and sealed,And the mixture was stirred at 100 ° C. for 12 hours.After the reaction vessel was cooled to room temperature, 1 mL of a saturated aqueous solution of ammonium chloride was added, and the mixture was extracted three times with 8 mL of ethyl acetate, and the obtained organic phases were combined.The solvent was distilled off under reduced pressure, and the residue was purified using silica gel column chromatography (hexane: chloroform: ethyl acetate = 4: 1: 0 to 4: 1: 1)92 mg (white solid, yield 75percent) of 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide was obtained.
Reference：
[1] Organic and Biomolecular Chemistry, 2014, vol. 12, # 22, p. 3604 - 3610
[2] Organic Letters, 2011, vol. 13, # 21, p. 5766 - 5769
[3] Patent: JP5699037, 2015, B2, . Location in patent: Paragraph 0091; 0092
2
[ 698-67-9 ]
[ 73183-34-3 ]
[ 179117-44-3 ]
Yield
Reaction Conditions
Operation in experiment
79%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃;
A mixture of 2-70 (1.0 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 °C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified via column chromatography on silica gel eluting with DCM/MeOH from 20/1 to 10/1 to give intermediate 2-71 (yellow solid, 975 mg, 79percent yield). LCMS (m/z):248 [M+Hj .
Reference：
[1] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[2] Patent: WO2016/161145, 2016, A1, . Location in patent: Paragraph 00743
[3] European Journal of Medicinal Chemistry, 2015, vol. 96, p. 382 - 395
3
[ 180516-87-4 ]
[ 179117-44-3 ]
Yield
Reaction Conditions
Operation in experiment
45%
With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3 h;
Step 1 4-(4,4,5,5-Metramethyl-1,3,2-dioxaborolan-2-yl)benzamide Procedure To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45percent) as a yellow solid. LC-MS: 248 [M+H]+, tR=1.421 min.
Reference：
[1] Patent: US2012/252777, 2012, A1, . Location in patent: Page/Page column 96
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040
Reference：
[1] Journal of the American Chemical Society, 2017, vol. 139, # 23, p. 7745 - 7748
[2] Angewandte Chemie - International Edition, 2018, [3] Angew. Chem., 2018, vol. 130, p. 15988 - 15992,5
8
[ 586-76-5 ]
[ 179117-44-3 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040
9
[ 73183-34-3 ]
[ 179117-44-3 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040
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