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Chemistry
Organometallic Reagents
Organoboron
(3,5-Difluoro-4-(hydroxymethyl)phenyl)boronic acid
Chemistry
Organometallic Reagents
Organic Building Blocks
Organoboron
Organoboron Aryls Fluorinated Building Blocks Alcohols Benzene Compounds

[ CAS No. 917969-79-0 ]

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Chemical Structure| 917969-79-0
Chemical Structure| 917969-79-0
Structure of 917969-79-0 * Storage: {[proInfo.prStorage]}

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Product Details of [ 917969-79-0 ]

CAS No. :917969-79-0 MDL No. :MFCD03095141
Formula : C7H7BF2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :187.94 g/mol Pubchem ID :-
Synonyms :

Safety of [ 917969-79-0 ]

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 [ 917969-79-0 ]

  • Downstream synthetic route of [ 917969-79-0 ]

[ 917969-79-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 917969-46-1 ]
  • [ 917969-79-0 ]
  • 7-(4-chlorophenyl)-8-(3,5-difluoro-4-(hydroxymethyl)phenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
36% With potassium phosphate In tetrahydrofuran at 90℃; for 12h; 72 Example 72 Preparation of 7-(4-chlorophenyl)-8-(3,5-difluoro-4-(hydroxymethyl)phenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one To a stirring solution of 8-bromo-7-(4-chlorophenyl)-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (60 mg, 0.12 mmol) in THF (2 mL) at room temperature under argon was added 3,5-difluoro-4-hydroxymethylphenylboronic acid (68.0 mg, 0.36 mmol), Pd(dppf)Cl2.CH2Cl2 (9.8 mg, 0.011 mmol), and K3PO4 (77 mg, 0.36 mmol). The resulting suspension was purged of oxygen by bubbling with argon for 15 min, sealed in a vial under argon, heated at 90° C. for 12 h, and then cooled to room temperature. Analysis by HPLC/MS indicated that starting material was still present and one major new product had formed. The reaction mixture was diluted with EtOAc and washed once with brine. The organic layer was dried (MgSO4), filtered, and concentrated under reduced pressure. The crude product was purified by automated silica gel chromatography (eluted with EtOAc/hexanes). Pooling of the desired fractions, washing with saturated aq. NaHCO3 solution to eliminate any possible boronic acid contaminant, drying the organic phase (MgSO4), filtering and evaporation provided the title compound as a yellow solid, 24 mg, 36%. HPLC/MS: retention time=3.66 min, [M+H]+=561. 1H NMR (CDCl3): δ 7.85 (d, J=7.1 Hz, 1H), 7.69 (d, J=8.3 Hz, 1H), 7.49 (d, J=7.7 Hz, 1H), 7.28 (m, 2H), 7.08 (m, 2H), 6.81 (d, J=7.7 Hz, 2H), 6.63 (d, J=7.1 Hz, 1H), 5.23 (s, 2H), 4.75 (d, J=2.8 Hz, 2H), 2.74 (s, 3H), 2.01 (t, J=5.5 Hz).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/4772, 2007, A1 Location in patent: Page/Page column 44
  • 2
  • [ 1417736-43-6 ]
  • [ 917969-79-0 ]
YieldReaction ConditionsOperation in experiment
With water; acetic acid Intermediate 2A [3,5-Difluoro-4-(hydroxymethyl)phenyl]boronic acid Intermediate 2A [3,5-Difluoro-4-(hydroxymethyl)phenyl]boronic acid [4-([ter -Butyl(dimethyl)silyl]oxy}methyi)-3,5-difSuoi phenyl]boronic acid (19.3 g, 63.9 mmol; crude material, prepared by the method of Hattori, Bioorg. Med. Chem. 2006. 14, 3258-3262) was dissolved in 400 ml. aqueous acetic acid (66%) and stirred at 40°C for 5 h. The solution was then evaporated under reduced pressure, and the residue was purified by flash chromatography over silica gel (gradient elution from 0% to 2% methanol in dichloromethane) to give 3.46 g (25% of th., LC-MS purity 87%) of the title compound. LC-MS (method 7): t = 0.50 min; MS (ESIpos): m/z (%) = 171.2 (100) [M-OH]+, MS (ESIneg): m/z (%) = 187.3 (100) [M-1 IJ .
Reference： [1]Current Patent Assignee: BAYER AG - WO2013/4551, 2013, A1 Location in patent: Page/Page column 34
  • 3
  • [ 162744-59-4 ]
  • [ 917969-79-0 ]
Reference： [1]Patent: WO2013/4551,2013,A1
  • 4
  • [ 917969-79-0 ]
  • C26H32IN5O4S [ No CAS ]
  • C33H37F2N5O5S [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; Cs2CO3 In tetrahydrofuran at 120℃; for 0.333333h; Microwave irradiation; Inert atmosphere; 3-(3-HO-Me-Ph)-Phs-Phe(3-CN)-Pip-4-Urea-tBu (S18) General procedure: The halide S9 (100 mg, 0.16 mmol, 1.0 eq.), 3-(hydroxymethyl)-phenylboronic acid (33 mg, 0.22 mmol, 1.4 eq.), Pd(OAc)2 (1.1 mg, 4.7 μmol, 3 mol%), and SPhos (3.9 mg, 9.4 μmol, 6 mol%) were dissolved in 1 mL THF and 0.31 mL 2 M aq. Cs2CO3 solution (2 mL/mmol halide) in a microwave vial. After passing Ar into the solution for 5 min, the vial was sealed and the mixture stirred in a microwave at 120 °C for 80 min. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic phase was submitted to a series of washing steps (2 x Aq.demin → 1 x brine), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Lastly, the obtained crude was purified via column chromatography (silica gel, EtOAc/MeOH 100:1) to obtain the pure product S18 as a colorless solid (56 mg, 91 μmol).
43% With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; palladium diacetate; Cs2CO3 In tetrahydrofuran at 120℃; for 0.333333h; Microwave irradiation; Inert atmosphere; 3-(3-HO-Me-Ph)-Phs-Phe(3-CN)-Pip-4-Urea-tBu (S18) General procedure: The halide S9 (100 mg, 0.16 mmol, 1.0 eq.), 3-(hydroxymethyl)-phenylboronic acid (33 mg, 0.22 mmol, 1.4 eq.), Pd(OAc)2 (1.1 mg, 4.7 μmol, 3 mol%), and SPhos (3.9 mg, 9.4 μmol, 6 mol%) were dissolved in 1 mL THF and 0.31 mL 2 M aq. Cs2CO3 solution (2 mL/mmol halide) in a microwave vial. After passing Ar into the solution for 5 min, the vial was sealed and the mixture stirred in a microwave at 120 °C for 80 min. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic phase was submitted to a series of washing steps (2 x Aq.demin → 1 x brine), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. Lastly, the obtained crude was purified via column chromatography (silica gel, EtOAc/MeOH 100:1) to obtain the pure product S18 as a colorless solid (56 mg, 91 μmol).
Reference： [1]Pilgram, Oliver; Keils, Aline; Benary, Gerrit E.; Müller, Janis; Merkl, Stefan; Ngaha, Sandrine; Huber, Simon; Chevillard, Florent; Harbig, Anne; Magdolen, Viktor; Heine, Andreas; Böttcher-Friebertshäuser, Eva; Steinmetzer, Torsten [European Journal of Medicinal Chemistry, 2022, vol. 238]
[2]Pilgram, Oliver; Keils, Aline; Benary, Gerrit E.; Müller, Janis; Merkl, Stefan; Ngaha, Sandrine; Huber, Simon; Chevillard, Florent; Harbig, Anne; Magdolen, Viktor; Heine, Andreas; Böttcher-Friebertshäuser, Eva; Steinmetzer, Torsten [European Journal of Medicinal Chemistry, 2022, vol. 238]

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