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Heterocyclic Building Blocks
Organoboron
isoindolin
2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one
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isoindolin

[ CAS No. 1002309-19-4 ] {[proInfo.proName]}

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Chemical Structure| 1002309-19-4
Chemical Structure| 1002309-19-4
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Product Details of [ 1002309-19-4 ]

CAS No. :1002309-19-4 MDL No. :MFCD14706581
Formula : C15H20BNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SQEOPRRAMPXMMO-UHFFFAOYSA-N
M.W : 273.14 Pubchem ID :57691224
Synonyms :

Safety of [ 1002309-19-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1002309-19-4 ]

* 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 [ 1002309-19-4 ]

[ 1002309-19-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 868066-91-5 ]
  • [ 73183-34-3 ]
  • [ 1002309-19-4 ]
YieldReaction ConditionsOperation in experiment
89% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 85℃;Inert atmosphere; [00532] Intermediate Sic: 2-methyl-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yI)isoindolin-1-one[00533] A round bottomed flask containing bis(pinacolato)diboron (354mg, 1 .3gmmol) and KOAc (326mg, 3.32mmol) in 1 ,4-dioxane (6.5mL) was evacuated/backfilled with nitrogen. Pd(dppt)C12.CH2CI2 (54mg, 0.O7mmol) was added and the flask was evacuated/backfilled with nitrogen again. The reaction mixture was then stirred and heated at 85 C overnight. After this timethe mixture was cooled to room temperature, filtered through a plug of celite and the solid was washed with EtOAc. The filtrate was concentrated and the residue purified by column chromatography using an eluent of 0-100% EtOAc in heptane to give 2-methyl-5-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one (324mg,1.lgmmol, 89% yield) as a brown solid.1H NMR (CDCI3, 400MHz) O/ppm: 7.92 (1H, dd, J= 7.6Hz, 0.4Hz), 7.90-7.89 (1H, m), 7.85 (1H, dd, J 7.6Hz, 0.4Hz), 4.39 (2H, 5), 3.23 (3H, 5), 1.38 (12H, 5).MS Method 3: RT: 3.61 mi m/z 274.1 [M+H]
With potassium acetate; XPhos;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 85℃; for 22h; In a sealable tube was combined Pd2dba3 (0.0270 g, 0.0295 mmol), 2- (dicyclohexylphosphino) -2' , 4', 6'- tri-i-propyl-1, 1' -biphenyl (0.0563 g, 0.118 mmol) , 4 , 4, 5, 5- tetramethyl-2- (4,4, 5 , 5-tetramethyl-l, 3 , 2-dioxaborolan-2-yl) - 1, 3, 2-dioxaborolane (0.450 g, 1.77 mmol), 5-bromo-2- <n="113"/>methylisoindolin-1-one (see Tsuritani, T., et al Synlett 2006, 5 801-803} (0.267 g, 1.18 mmol) , potassium acetate (0.232 g, 2.36 mmol) and 2 mL dioxane . The mixture was blanketed with N2, sealed and heated at 80 C for 22 h. The mixture was allowed to cool to rt then diluted with EtOAc, and the organic layer washed with water, sat. NaHCO3, then dried over Na2SO4, filtered and evaporated. The residue was purified via flash chromatography using a EtOAc in CH2Cl2 gradient. The title compound was collected as a tan solid.
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere of nitrogen; To a solution of 5-bromo-2-methylisoindolin-l-one (Example 31, step (i), 60.4 g) in dioxane (2 L) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (67.8 g), potassium acetate (65.4 g) and Pd(dppf)Cl2 (6 g) under an atmosphere of nitrogen. The mixture was heated to 1000C and stirred for 4 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the crude product was purified by chromatography on silica eluting with petroleum ether / ethyl acetate (6:1 to 2: 1) to afford the sub-titled compound (72 g).1H NMR (400 MHz, CDCl3): delta 7.89-7.88 (m, 2H), 7.83-7.81 (m, IH), 4.35 (s, 2H), 3.19 (s, 3H), 10.34 (s, 12H).
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl acetamide; at 100℃;Inert atmosphere; Step B: 2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l-one [0236] 5-Bromo-2-methylisoindolin-l-one (0.112 g, 0.495 mmol), bis(pinacolato)diboron (0.189 g, 0.743 mmol), potassium acetate (0.146 g, 1.486 mmol), and PdCl2(dppf)CH2Cl2 adduct (0.020 g, 0.025 mmol) were suspended in DMA (1.0 mL). The mixture was degassed with N2 and heated in a sand bath at 100C overnight. The reaction mixture was subsequently cooled, diluted with EtOAc (10 mL), and passed through a syringe filter. The filtrate was diluted with water (10 mL) and the layers were separated. The aqueous layer was washed with EtOAc (2 x 5 mL). The organic layers were combined and concentrated in vacuo to give the title compound as a brown residue, which was used without further purification.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90℃;Inert atmosphere; In a vial was combined <strong>[868066-91-5]5-bromo-2-methylisoindolin-1-one</strong> (226 mg, 1.00 mmol) [Ark Pharm cat AK-37748], 4,4,5,5,4?,4?,5?,5?-octamethyl-[2,2?]bi[[1,3,2]dioxaborolanyl] (0.533 g, 2.10 mmol), potassium acetate (294 mg, 3.00 mmol), 1,4-dioxane (5.0 mL), and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (36.6 mg, 0.050 mmol). The vial was de-gassed by bubbling nitrogen through the solvent for 5 minutes then heated to 90 C. overnight. The mixture was allowed to cool to room temperature and was then filtered using a syringe filter. The filtrate was then concentrated under reduced pressure and used without further purification. LC-MS calculated for C15H21BNO3(M+H)+: m/z=274.2. found 274.1.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 5h; 5-Bromo-2-methylisoindolin-1-one synthesized in step 1 (Formula 5-2, 2.1 g, 9.20 mmol), potassium acetate (2.26 g, 23 mmol, 2.5 eq), Pd (dppf) Cl 2 -CH 2 Cl 2 (0.225 g, 0.28 mmol, 0.03 eq) and B 2 Pin 2 (2.34 g, 9.20 mmol, 1 eq) were dissolved in 1,4-dioxane (20 ml). The temperature was raised to 100 ° C and the reaction mixture was stirred for 5 hours.After completion of the reaction, the mixture was extracted with dichloromethane. The organic layer was washed sequentially with H 2 O and brine, then dried over anhydrous MgSO 4,The solvent was removed under reduced pressure.Thereafter, the reaction mixture was separated and purified by MPLC (hexane / ethyl acetate; 70:30) to obtain the target compound (Formula 5-3).

Reference： [1]Patent: WO2016/51193,2016,A1 .Location in patent: Paragraph 00527; 00532; 00533
[2]Patent: WO2008/8539,2008,A2 .Location in patent: Page/Page column 111-112
[3]Patent: WO2010/128324,2010,A1 .Location in patent: Page/Page column 119
[4]Patent: WO2013/148603,2013,A1 .Location in patent: Paragraph 0235-0236
[5]Patent: US2016/9712,2016,A1 .Location in patent: Paragraph 0783
[6]Patent: KR2019/109007,2019,A .Location in patent: Paragraph 0219; 0223-0225
  • 2
  • [ 1002309-19-4 ]
  • [ 1190875-38-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; water In acetone for 18h; Heating; Reflux; 31.iii To a solution of crude 2-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)isoindolin-l- one (Example 31, step (ii), 53 g) in acetone (600 rnL) was added aqueous HCl solution (2M, 600 rnL) and the solution was heated at reflux for 18 h. The solution was concentrated under vacuum to remove acetone and then cooled to 100C. The resulting precipitate was filtered and dried under vacuum to afford the sub-titled compound (26.8 g).1H NMR (400 MHz, CDCl3): δ 8.21 (s, 2H), 7.91 (s, IH), 7.86-7.84 (d, IH), 7.59-7.58 (d, IH), 4.428 (s, 2H), 3.05 (s, 3H).
Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2010/128324, 2010, A1 Location in patent: Page/Page column 120
YieldReaction ConditionsOperation in experiment
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 1-(2-([2,2'-bipyridin]-5-yl)phenyl)-3-cyclohexylthiourea; In para-xylene; at 25.0℃; for 24.0h; General procedure: Meta- selective l3orylation of an Aromatic Compoundwith an Iridium Catalyst. In a dried test tube, to a p-xylene (1.5 mE) solution of N,N-dihexylbenzamide (72.4 mg, 0.250 mmol, 1.00 equiv), [Ir(OMe) (cod)]2 (1.2 mg, 1.9 jtmol, 0.75 mol %), 1 -(2-([2,2?-bipyridin]-S-yl) phenyl)-3-cyclohexylurea (1.2 mg, 3.8 tmol, 1.5 mol %) andbis (pinacolato)diboron (47.6 mg, 0.188 mmol, 0.750 equiv) were added and stirred at 25 C. for 24 hours. The solvent was removed under reduced pressure, and then the products were isolated and prepared by recycling preparative HPLC.63% yield [meta/para=7.5]; colorless oil; 11B NMR (130 MHz, CDCl3) delta 31.9; IR (neat, nu/cm -1) 2930, 1627, 1410, 1355, 1140, 1027, 965, 851, 754, 683; HRMS (ESI+) Calcd for C25H44BNNaO4 ([M+Na]+) 468.3256, Found 468.3246. N,N-Dihexyl-2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide: 1H NMR (400 MHz, CDCl3) delta 0.80 (t, J=7.4 Hz, 3H), 0.91 (t, J=6.7 Hz, 3H), 1.06-1.08 (m, 4H), 1.16-1.50 (m, 22H), 1.62-1.64 (m, 2H), 3.01-3.04 (m, 2H), 3.48-3.49 (m, 2H), 3.82 (s, 3H), 6.87 (d, J=8.3 Hz, 1H), 7.63 (s, 1H), 7.76 (d, J=8.3 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta 14.1, 14.2, 22.5, 22.8, 24.7, 26,3, 26.7, 27.6, 28.4, 31.4, 31.8, 44.4, 48.5, 55.4, 83.7, 110.1, 126.6, 134.4, 137.0, 157.8, 169.2. N,N-Dihexyl-2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide: 1H NMR (400 MHz, CDCl3) delta 0.80 (t, J=7.4 Hz, 3H), 0.91 (t, J=6.7 Hz, 3H), 1.06-1.08 (m, 4H), 1.18-1.50 (m, 20H), 1.62-1.64 (m, 4H), 3.01-3.04 (m, 2H), 3.48-3.49 (m, 2H), 3.85 (s, 3H), 7.17 (d, J=7.2 Hz, 1H), 7.29 (s, 1H), 7.41 (d, J=7.2 Hz, 1H); 13C NMR (125 MHz, CDCl3) delta 14.1, 14.2, 22.5, 22.8, 25.0, 26,3, 26.8, 27.5, 28.4, 31.4, 31.8, 44.3, 48.3, 55.6, 84.1, 116.4, 127.1, 127.4, 130.0, 154.6, 169.2.

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