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Chemistry
Organometallic Reagents
Organoboron
2-Methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline
Chemistry
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Heterocyclic Building Blocks Organic Building Blocks Boronic acids/esters
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Tetrahydroisoquinolines Esters Aromatic Borons

[ CAS No. 922718-57-8 ] {[proInfo.proName]}

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Chemical Structure| 922718-57-8
Chemical Structure| 922718-57-8
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Product Details of [ 922718-57-8 ]

CAS No. :922718-57-8 MDL No. :MFCD11044665
Formula : C16H24BNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :QRMAQYCEYDOEGC-UHFFFAOYSA-N
M.W : 273.18 Pubchem ID :16102686
Synonyms :

Safety of [ 922718-57-8 ]

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

Application In Synthesis of [ 922718-57-8 ]

* 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 [ 922718-57-8 ]

[ 922718-57-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 675576-26-8 ]
  • [ 922718-57-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 8 h / 20 °C 2: H2 / PtO2 / ethanol / 24 h / 20 °C / 2280 Torr
Reference： [1]Wang, Qiuping; Lucien, Edlaine; Hashimoto, Akihiro; Pais, Godwin C. G.; Nelson, David M.; Song, Yongsheng; Thanassi, Jane A.; Marlor, Christopher W.; Thoma, Christy L.; Cheng, Jijun; Podos, Steven D.; Ou, Yangsi; Deshpande, Milind; Pucci, Michael J.; Buechter, Douglas D.; Bradbury, Barton J.; Wiles, Jason A. [Journal of Medicinal Chemistry, 2007, vol. 50, # 2, p. 199 - 210]
  • 2
  • [ 14097-39-3 ]
  • [ 922718-57-8 ]
Reference： [1]MedChemComm,2014,vol. 5,p. 1533 - 1539
  • 3
  • [ 59961-00-1 ]
  • [ 73183-34-3 ]
  • [ 922718-57-8 ]
YieldReaction ConditionsOperation in experiment
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 25 - 90℃; for 14h; Inert atmosphere; 1.i Step I: Bis(pinacolato)diboron (28.05 g, 110.46 mmol) and KOAc (14.45 g, 147.27 mmol) were added to a solutionof 6-bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline (16.65 g, 73.64 mmol) in dioxane (150 mL) at 25°C under theprotection of nitrogen gas, followed by the addition of a catalyst Pd(dppf)Cl2·CH2Cl2 (6.01 g, 7.36 mmol). The mixturewas stirred at 25°C for 10 min, and then heated to 90°C with stirring for 14 hours. The mixture was cooled down to 25°C and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100∼200mesh of silica gel, dichloromethane/methanol = 10/0 to 1/1) to give the title product (31.0 g, crude product) as ablack solid, which was used directly in the next step. MS (ESI) M/Z: 274 (M + 1).
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; Further stages; A mixture of 6-bromo-2-methyl-3, 4-dihydro- liT-isoquinoline (220 mg, 973 pmol, 1.00 equiv), 4, 4, 5, 5-tetramethyl-2-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl) -1, 3, 2- dioxaborolane (494 mg, 1.95 mmol, 2.00 equiv), potassium acetate (191 mg, 1.95 mmol, 2.00 equiv), Pd(dppf)Cl2 (71.2 mg, 97.3 pmol, 0.10 equiv) in dioxane (3.00 mL) was purged with nitrogen and subsequently stirred at 100 °C for 2 h. The mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by prep-TLC (petroleum ether/ethyl acetate = 2/1) to afford 2-methyl-6-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)-3, 4-dihydro- H- isoquinoline (150 mg, crude) as a white solid.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; A mixture of 6-bromo-2-methyl-3,4-dihydro-1H-isoquinoline (220 mg, 973 μmol, 1.00 equiv), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3,2- dioxaborolane (494 mg, 1.95 mmol, 2.00 equiv), potassium acetate (191 mg, 1.95 mmol, 2.00 equiv), Pd(dppf)Cl2 (71.2 mg, 97.3 μmol, 0.10 equiv) in dioxane (3.00 mL) was purged with nitrogen and subsequently stirred at 100 °C for 2 h. The mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by prep-TLC (petroleum ether/ethyl acetate = 2/1) to afford 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro- 1H-isoquinoline (150 mg, crude) as a white solid.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; [0325] A mixture of 6-bromo-2-methyl-3,4-dihydro-1H-isoquinoline (220 mg, 973 mol, 1.00 equiv), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,3,2- dioxaborolane (494 mg, 1.95 mmol, 2.00 equiv), potassium acetate (191 mg, 1.95 mmol, 2.00 equiv), Pd(dppf)Cl2 (71.2 mg, 97.3 mol, 0.10 equiv) in dioxane (3.00 mL) was purged with nitrogen and subsequently stirred at 100 °C for 2 h. The mixture was filtered and concentrated in vacuo to give a residue. The residue was purified by prep-TLC (petroleum ether/ethyl acetate = 2/1) to afford 2-methyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline (150 mg, crude) as a white solid.

Reference： [1]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3248968, 2017, A1 Location in patent: Paragraph 0074
[2]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2019/152419, 2019, A1 Location in patent: Paragraph 0332; 0334
[3]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2020/219448, 2020, A1 Location in patent: Paragraph 0384
[4]Current Patent Assignee: MILA MEDICAL SHARE LTD COMPANY; MIRATI THERAPEUTICS, INC. - WO2020/247475, 2020, A1 Location in patent: Paragraph 0325
  • 4
  • [ 226942-29-6 ]
  • [ 922718-57-8 ]
Reference： [1]Patent: WO2019/152419,2019,A1

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