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[ CAS No. 893566-72-8 ]

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Chemical Structure| 893566-72-8
Chemical Structure| 893566-72-8
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CAS No. :893566-72-8 MDL No. :MFCD11044669
Formula : C20H30BNO4 Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :359.27 g/mol Pubchem ID :-
Synonyms :

Safety of [ 893566-72-8 ]

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 [ 893566-72-8 ]

  • Downstream synthetic route of [ 893566-72-8 ]

[ 893566-72-8 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 893566-75-1 ]
  • [ 893566-74-0 ]
  • [ 73183-34-3 ]
  • [ 893566-72-8 ]
  • [ 893566-73-9 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 85℃; for 4h; A solution of tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate and <strong>[893566-75-1]tert-butyl 8-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate</strong> (19.5 mmol), bis(pinacolato)diboron (21.4 mmol) and potassium acetate (61 mmol) in DMF (100 mL) was degassed. To this solution was added PdCl2dppf (1:1 complex with DCM, 0.8 mmol). The reaction mixture was heated at 85 C. for 4 hr and then allowed to cool to room temperature and diluted with EtOAc. The solution was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate and tert-butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate. LCMS: (FA) ES+360 (for each).
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 81℃; tert-Butyl 6-( 4,4,5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-vD-3 ,4-dihvdroisoquinoline- 2(liD-carboxylate is A 3:1 mixture (0.49 g, 1.6 mmol) of fert-butyl 6-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate and tert-butyl 8~bromo-3,4-dihydroisoquinoline-2(li/)- carboxylate, bis(pinacolato)diborane (0.45 g, 1.8 mmol), PdCl2 x dppf (0.039 g, 0.048 mmol), potassium acetate (0.48 g, 4.8 mmol) and DMF (8.0 mL) was heated at 81 C ' WeligKtyThe~slve1alphat^30 twice with EtOAc. The organic phase was dried, filtered and concentrated. Column chromatography with EtO Ac-heptanes (1:10 through 1:4) gave 0.24 g of a 4:1 mixture of EPO <DP n="25"/>the title product and ter/-butyl 8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2(lH)-carboxylate.1H NMR (CDCl3) delta 7.62 (d, IH), 7.60 (s, IH), 7.13 (d, IH), 4.59 (s, 2H), 3.64 (t, 2H), 2. .85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (6-isomer). 1H NMR (CDCl3) delta 7.69 (d, IH), 7.24-7.14 (m's, 2H), 4.88 (s, 2H), 3.64 (t, 2H), 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (8-isomef).
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 81℃; A 3:1 mixture (0.49 g, 1.6 mmol) of tert-mty 6-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate and fert-butyl 8-bromo-3,4-dihydroisoquinoline-2(lH)- carboxylate, bis(pinacolato)diborane (0.45 g, 1.8 mmol), PdCl2 x dppf (0.039 g, 0.048 mmol), potassium acetate (0.48 g, 4.8 mmol) and DMF (8.0 mL) was heated at 81 0C overnight. The solvent was evaporated, the residue taken up in water-brine and washed twice with EtOAc. The organic phase was dried, filtered and concentrated. Column chromatography with EtOAc-heptanes (1:10 through 1:4) gave 0.24 g of a 4:1 mixture of the title product and tert-butyl 8-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2( lH)-carboxylate.1H NMR (CDCl3) delta 7.62 (d, IH), 7.60 (s, IH), 7.13 (d, IH), 4.59 (s, 2H), 3.64 (t, 2H)5 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (6-isomer). 1H NMR (CDCl3) delta 7.69 (d, IH), 7.24-7.14 (m, 2H)5 4.88 (s, 2H), 3.64 (t, 2H), 2.85 (t, 2H), 1.50 (s, 9H) and 1.35 (s, 12H) ppm (8-isomer).
  • 2
  • [ 866602-85-9 ]
  • [ 893566-72-8 ]
  • [ 893566-73-9 ]
  • [ 893566-71-7 ]
YieldReaction ConditionsOperation in experiment
48% With sodium carbonate In ethanol; water; toluene at 81℃; for 6.16667h; 1 te/Y-Butyl 6-[2-(trifluoromemyl)pyrirm'din-5-yll-3,4-d]ivdroisoquinorine-2(lH)- carboxylateA 4:1 mixture (0.10 g, 0.28 mmol) offers-butyl 6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate and tert-bvftyl 8-(4,4,5,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)=3 ,4-dihydroisoqioline-2(lH)-carbbxylate~ EPO 2-(trifluoromethyl)pyrimidin-5-yl trifluoromethanesulfonate (0.083 g, 0.28 mmol), PdCl2 x dppf (0.0048 g), 2M sodium carbonate (1.1 mL), toluene (4.0 niL) and EtOH (1.0 mL) was purged with dry argon for ten minutes then heated in a sealed vial at 81 0C for 6 h. The black solution was filtered through glass-wool, taken up in water-brine and washed twice with EtOAc. The combined organic phases were dried, filtered and concentrated with silica (5 g). Column chromatography with EtOAc-heptanes (1:8 through 1:5) gave 0.051 g (48%) of the title product as white solid. LC-MS m/z 380 (M+l);1H NMR (CDCl3) δ 9.06 (s, 2H), 7.44 (dd, IH)3 7.38 (br s, IH), 7.30 (d, IH), 4.66 (s, 2H), 3.71 (t, 2H)52.95 (t, 2H), and 1.51 (s, 9H) ppm.
  • 3
  • [ 304902-96-3 ]
  • [ 893566-72-8 ]
  • [ 893566-73-9 ]
  • [ 893567-06-1 ]
YieldReaction ConditionsOperation in experiment
36% With sodium carbonate In ethanol; water; toluene at 81℃; for 6.16667h; 1 fert-Butyl 6-[2-(cvclopropyϖpyrimidin-5-vn-3,4-dihydroisoquinoline-2(lH)- carboxylateA 4:1 mixture (0.097 g, 0.27 mmol) of tert-butyl 6-(4,4,5,5-tetramethyl-l,3,2- io dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate and tert-butyl 8-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(lH)-carboxylate, 5-bromo-2-cyclopropylpyrimidine (0.054 g, 0.27 mmol), PdCl2 x dppf (0.0045 g), 2M sodium carbonate (1.0 mL), toluene (4.0 mL) and EtOH (1.0 rnL) was purged with dry argon for ten minutes, then heated in a sealed vial at 81 °C for 6 h. The black solution was is filtered through glass-wool, taken up in water-brine and washed twice with EtOAc. The combined organic phases were dried, filtered and concentrated with silica (5 g). Column chromatography with EtO Ac-heptanes (1:5 through 1:2) gave 0.034 g (36%) of the title product as white solid. LC-MS m/z 352 (M+l);20 1H NMR (CDCl3) δ 8.74 (s, 2H), 7.35 (dd, IH), 7.29 (s, IH), 7.22 (d, IH), 4.62 (s, 2H), 3.68 (t, 2H), 2.90 (t, 2H), 2.30 (m, IH), 1.50 (s, 9H), 1.18 (m, 2H) and 1.11 (m, 2H) ppm.
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 100℃; for 3h; 13.1 N,N-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1-benzofuran-2-carboxamide General procedure: A mixture of 5-bromo-N,N-dimethyl-2,3-dihydro-1-benzofuran-2-carboxamide (0.235 g, 0.870 mmol), 4,4,5,5,4',4',5',5'-octamethyl-[2,2']bi[[1,3,2]dioxaborolanyl] (0.243 g, 0.957 mmol) (Aldrich Cat. No. 473294), potassium acetate (0.213 g, 2.17 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (36 mg, 0.043 mmol); and 1,1'-bis(diphenylphosphino)ferrocene (0.024 g, 0.043 mmol) in 1,4-dioxane (4.3 mL) was degassed and stirred at 100° C. for 3 h. After cooling the mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%) to afford the desired product (0.27 g, 98%). LCMS (M+H)+=318.1.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In dimethyl sulfoxide at 80℃; for 16.5h; Inert atmosphere; V-20 1,1-Dimethylethyl (4,4-dimethylcyclohexyl)(2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]oxy}ethyl)carbamate General procedure: A mixture of {2-[(4-bromophenyl)oxy]ethyl}(4,4-dimethylcyclohexyl) carbamate (0.529 g; 1.24 mmol; Example V-8 above), bis(pinacolato)diboron (0.439 g; 1.86 mmol), KOAc (0.365 g; 3.72 mmol), and PdCl2(dppf).CH2Cl2(0.030 g; 0.037 mmol) in anhyd DMSO (5 mL) was sparged with N2for 5 min, then heated to 80° C. under N2. After 16.5 h the mixture was cooled, poured into H2O and extracted with EtOAc (×3). Combined organics were washed (H2O, brine), dried over Na2SO4, adsorbed onto a small amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a colorless gum.
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; for 15h; Inert atmosphere; 4.2 Step 1: Synthesis of Compound WX128-2 General procedure: A solution of WX128-1 (2.00 g, 6.41 mmol), bis(Pinacolato)Diboron (1.79 g, 7.05 mmol) and potassium acetate (1.89 g, 19.22 mmol) in dioxane (20.00 mL) was purged with nitrogen gas for three times, and then to the system was added Pd(dppf)Cl2 (1.41 g, 1.92 mmol). The reaction mixture was reacted at 80° C. under a nitrogen atmosphere for 15 hours. After the reaction was complete, it was concentrated under reduced pressure. The residue was dissolved in 30 mL water, and extracted with ethyl acetate (30 mL×3). The organic layers were combined, and washed with brine (50 mL×3), dried over anhydrous sodium sulfate, filtered and concentrated to afford Compound WX128-2 (3.38 g, crude product), dark brown oil. 1H NMR (400 MHz, CDCl3) δ 7.63-7.54 (m, 2H), 7.15 (d, J=7.5 Hz, 1H), 4.59 (s, 2H), 3.65 (br s, 2H), 2.85 (br s, 2H), 1.49 (s, 9H), 1.35 (s, 12H).
  • 5
  • [ 893566-74-0 ]
  • [ 73183-34-3 ]
  • [ 893566-72-8 ]
YieldReaction ConditionsOperation in experiment
90.12% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 65℃; for 2h; Inert atmosphere; 13.2 Step 2) 2-(tert-butoxycarbonyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline To a solution of 6-bromo-2-(?ert-butoxycarbonyl)-l,2,3,4-tetrahydroisoquinoline (1.06 g, 3.4 mmol) in DMSO (16 mL) were added bis(pinacolato)diboron (1.28 g, 4.8 mmol), AcOK (1.59 g, 13.6 mmol) and Pd(PPh3)2Cl2 (0.61 g, 0.8 mmol) under N2 atmosphere. The reaction was heated at 65 °C for 2 h, then cooled to rt and filtered through a pad of Celite, which was washed with EtOAc (100 mL). The filtrate was washed with brine (50 mL), dried over anhydrous a2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 15/1) to give the title compound as a pale yellow solid (1.1 g, 90.12%). NMR (400 MHz, CDC13) δ (ppm): 7.62-7.59 (m, 2H), 7.12-7.10 (d, J= 7.52 Hz, 1H), 4.58 (s, 2H), 3.63 (t, J = 5.4 Hz, 2H), 2.85-2.82 (t, J= 5.32 Hz, 2H), 1.48 (s, 9H), 1.34 (s, 12H).
90.12% With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 65℃; for 2h; Inert atmosphere; 13.2 Step 2) Preparation of 2- (tert-butoxycarbonyl) -6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,2 , 3,4-tetrahydroisoquinoline Under nitrogen protection,6-bromo-2- (t-butoxycarbonyl) -1,2,3,4-tetrahydroisoquinoline (1.06g, 3.4mmol)Was dissolved in dimethylsulfoxide (16 mL)To this was added boronic acid pinacol ester (1.28 g, 4.8 mmol)Potassium acetate (1.59 g, 13.6 mmol) andPd (PPh3) 2Cl2 (0.61 g, 0.8 mmol).The reaction solution was stirred at 65 ° C for 2 hours,Cooled to room temperature and filtered through celite. The filter cake was washed with ethyl acetate (100 mL). The collected filtrate was washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate (v / v) = 15/1)The title compound was obtained as a pale yellow solid (1.1 g, 90.12%).
87% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 95℃; for 14h; Sealed tube; 278 Intermediate 278B: tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4- dihydroisoquinoline-2(1H)-carboxylate PdCl2(dppf)-CH2Cl2 adduct (0.915 g, 1.121 mmol) and potassium acetate (3.30 g, 33.6 mmol) were added to a degassed solution of tert-butyl 6-bromo-3,4- dihydroisoquinoline-2(1H)-carboxylate (3.5 g, 11.21 mmol) and BISPIN (3.70 g, 14.57 mmol) in dioxane (120 mL), the resulting mixture was stirred at 95 °C for 14 h in a sealed tube. The reaction mixture was diluted with ethyl acetate, filtered and washed with excess ethyl acetate. The filtrates were dried over sodium sulphate and concentrated to get crude compound. The crude compound was purified by ISCO using 40 g silica column, compound was eluted with 45% ethyl acetate in pet ether, the fractions were collected and concentrated to get tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.5 g, 9.74 mmol, 87% yield) as a light brown solid. LCMS Retention time: 1.74 min [A], MS (E+) m/z: 304.5 [M+H-tBu].
86% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 25 - 80℃; for 12h; Inert atmosphere; 67.A Step A: Bis(pinacolato)diboron (7.3 g, 29 mmol) and KOAc (7.1 g, 72 mmol) were added to a solution of t-butyl-6-bromo-1,2,3,4-tetrahydroisoquinolin-2-formate (7.5 g, 24 mmol) in DMF (100 mL) at 25°C under the protection ofnitrogen gas, followed by adding a catalyst Pd(dppf)Cl2·CH2Cl2 (5.3 g, 7 mmol). The mixture was stirred at 25°Cfor 10 min and then heated to 80°C with stirring for 12 hours. The mixture was cooled down to 25°C and pouredinto water (600 mL). The mixture was then extracted with EA (200 mL 3 2). The combined organic phase was driedwith anhydrous Na2SO4, filtered and concentrated in vacuum to give a crude product. The residue was purified bysilica gel chromatography (petroleum ether/ethyl acetate = 20/1 to 10/1) to give t-butyl-oxycarboryl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3 ,4-tetrahydroisoquinolin-2-formate (7.4 g, 21 mmol, 86% yield) as a whitesolid.
62.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; A mixture of tert- butyl 6-bromo-3, 4-dihydro- l //-isoquinoline-2-carboxylate (140 mg, 448 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 (228 mg, 897 pmol, 2.00 equiv), Pd(dppf)Cl2 (32.8 mg, 44.8 pmol, 0.10 equiv), potassium acetate (88.0 mg, 897 pmol, 2.00 equiv) in dioxane (1.00 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 /c/V-butyl 6-(4, 4, 5, 5 -tetramethyl-l, 3, 2-dioxaborolan-2-yl)- 3, 4-dihydro-lH-isoquinoline-2-carboxylate (100 mg, 278 pmol, 62.1% yield) as a yellow oil. 1H NMR (400MHz, CD3OD) d = 7.58 - 7.54 (m, 2H), 7.13 (d, J=8.0 Hz, 1H), 4.58 (br s, 2H), 3.65 (br t, J=6.0 Hz, 2H), 2.84 (t, =6.0 Hz, 2H), 1.35 (s, 12H), 1.19 (br s, 1H), 1.22 (s, 9H).
62.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; A mixture of tert-butyl 6-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate (140 mg, 448 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 (228 mg, 897 μmol, 2.00 equiv), Pd(dppf)Cl2 (32.8 mg, 44.8 μmol, 0.10 equiv), potassium acetate (88.0 mg, 897 μmol, 2.00 equiv) in dioxane (1.00 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 tert-butyl 6-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)- 3,4-dihydro-1H-isoquinoline-2-carboxylate (100 mg, 278 μmol, 62.1% yield) as a yellow oil. [0388] 1H NMR (400MHz, CD3OD) d = 7.58 - 7.54 (m, 2H), 7.13 (d, J = 8.0 Hz, 1H), 4.58 (br s, 2H), 3.65 (br t, J = 6.0 Hz, 2H), 2.84 (t, J = 6.0 Hz, 2H), 1.35 (s, 12H), 1.19 (br s, 1H), 1.22 (s, 9H).
62.1% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 2h; Inert atmosphere; [0328] A mixture of tert-butyl 6-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate (140 mg, 448 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 (228 mg, 897 mol, 2.00 equiv), Pd(dppf)Cl2 (32.8 mg, 44.8 mol, 0.10 equiv), potassium acetate (88.0 mg, 897 mol, 2.00 equiv) in dioxane (1.00 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 tert-butyl 6-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate (100 mg, 278 mol, 62.1 % yield) as a yellow oil. [0329] 1H NMR (400MHz, CD3OD) d = 7.58 - 7.54 (m, 2H), 7.13 (d, J=8.0 Hz, 1H), 4.58 (br s, 2H), 3.65 (br t, J=6.0 Hz, 2H), 2.84 (t, J=6.0 Hz, 2H), 1.35 (s, 12H), 1.19 (br s, 1H), 1.22 (s, 9H).
45% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane; water at 120℃; Inert atmosphere; S-58.1 Step 1 : Synthesis of tert-butyi 6-(4,4,5,5-tetramethy]-l,3,2-dioxaboro]an-2-yl)-3,4-dihydroisoquinoline-2(l H)-carboxylate. To a solution of /-butyl 6-bromo-3,4- dihydroisoquinoline-2(lH)-carboxylate (0.500 g, 1.60 mmol, 1.0 equiv) in dioxane (5 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (0.342 g, 1.92 mmol, 1.2 equiv), KOAc (0.23 g, 2.4 mmol, 1.5 equiv) and resulting reaction mixture was purged with N2 gas for 10 min. followed by the addition of PdCh(dppf).DCM (0.39 g, 0.04 mmol. 0..03 equiv). The resulting reaction mixture was heated at 120 °C for overnight. After the completion of reaction (monitored by TLC & LCMS), the mixture was diluted with water (100 mL) and extracted with ethyl acetate (2 x 100 mL). Combined organic extracts were washed with water (100 mL c 2) & brine ( 100 mL), dried over anhydrous NarSOr and concentrated. The erode product was purified by flash chromatography (0-20 % EtOAc/hexane as an eluent) to obtain tert-butyi 6-(4, 4,5,5- tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2( 1 H)-carboxylate (0.260 g, 45 % Yield) as an off white solid. LCMS 304.2 (Acid fragment) [M+H]
41% With potassium acetate In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; 25 1,1 -Dimethylethyl 6-bromo-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 24) (1.215 g, 3.89 mmol) and 4,4,445,5,5t,5l-octamethyl-2,2'-bi-1 ,3,2-dioxaborolane (1.087 g, 4.28 mmol) were dissolved in 1,4-dioxane (15 ml) and the resulting mixture was de-gassed under vacuum (ca 15 mbar) then flushed with nitrogen. 1,1'- bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex (0.171 g, 0.234 mmol) and 1,1'-bis(diphenylphosphino)ferrocene (0.129 g, 0.234 mmol) were added. The resulting mixture was stirred at room temperature for 5 minutes, then treated with potassium acetate (1.146 g, 11.68 mmol), stirred at 90 0C under nitrogen for 4 hours then cooled to room temperature. The mixture was dissolved with a saturated Na2CO3 aqueous solution (20 ml) and the insoluble material was filtered off. The filtrate was extracted twice with AcOEt (20 ml) and the combined organic were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (c- Hexane/AcOEf. 5 to 50% gradient) gave 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl- 1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (580 mg, 41%) as a pale yellow oil which solidified on standing. LCMS: retention time 1.42 min; no mass ion detected
Stage #1: 6-bromo-2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinoline; bis(pinacol)diborane In 1,4-dioxane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With potassium acetate In 1,4-dioxane at 90℃; for 4h; Inert atmosphere; 1 ,1-Dimethylethyl 6-bromo-3,4-dihydro-2(1 H)-isoquinolinecarboxylate (Preparation 64) (1.22g, 3.9 mmol) and bis(pinacolato)diboron (1.09g, 4.3 mmol) were dissolved in 1 ,4-dioxane (15ml), the mixture degassed under nitrogen at room temperature. 1 ,1'- Bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex (0.17g, 0.23 mmol) and 1 ,1'-bis(diphenylphosphino)ferrocene (0.13g, 0.23 mmol) were added the mixture stirred at room temperature for 5min. Potassium acetate (1.15g, 12 mmol) was added and the mixture heated at 900C under nitrogen for 4h. The reaction was allowed to cool to room temperature overnight, quenched with saturated sodium hydrogen carbonate solution (20ml) and filtered. This filtrate was extracted with ethyl acetate (2x 20ml), the combined organics washed with saturated brine, dried (MgSO4) and evaporated to give a dark brown oil. This oil was absorbed onto a 40+ samplet and dried in the vacuum oven, The samplet was washed with DCM / methanol This solution was evaporated and the brown residue was purified by chromatography on a silica cartridge eluting with an ethyl acetate / hexane gradient (5-50%). Product fractions were combined and evaporated to give 1 ,1- dimethylethyl 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate as a pale yellow oil (580mg). Stored in the freezer over the weekend to give a white solid LCMS (Method formate): Retention time 1.46min, MH+ not observed
With potassium acetate In 1,2-dimethoxyethane at 100℃; Inert atmosphere of N2; Microwave radiation; A suspension of tert-butyl-6-bromo-3,4-dihydroisoquinoline-2(lH)-carboxylate (1 eq, 0.320 mmol, 100 mg) in DME (2 ml) under an atmosphere of N2 is treated with dry potassium acetate (2 eq, 0.640 mmol, 63 mg). A mixture of bis-(pinacolato) diboron (1.2 eq,0.384 mmol, 98 mg) and PdCl2(dppf).DCM (0.04 eq, 0.0128 mmol, 9.4 mg) is added to the suspension and the resulting mixture is heated using microwave radiation at 100 0C for 1 hour. The mixture is filtered through Celite (filter material) and concentrated in vacuo to afford the title compound which is used without further purification; [M+H]+ = 360.
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere; 1.b Step b:
A mixture of tert-butyl 6-bromo-3,4-dihydroisoquinoline-2(1H)-carboxylate (3.12 g, 10.0 mmol), bis(pinacolato)diboron (3.05 g, 12.0 mmol), and KOAc (2.94 g, 30.0 mmol) in dioxane (50 mL) was degassed (N2) for 20 minutes. [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) complex with dichloromethane (817 mg, 1.0 mmol) was added, and the reaction mixture was degassed (N2) for an additional 5 minutes and stirred at 80° C. overnight under N2. The reaction mixture was cooled to room temperature, diluted with sat. NaHCO3 (100 mL), and extracted with EtOAc (3*100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered, and concentrated. Purification by silica gel flash chromatography (0-30% EtOAc/hexanes) gave tert-butyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate.

Reference: [1]Current Patent Assignee: CALITOR SCIENCES LLC; SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - WO2014/89324, 2014, A1 Location in patent: Paragraph 0237; 0245
[2]Current Patent Assignee: CALITOR SCIENCES LLC; SHENZHEN DONGYANGGUANG INDUSTRIAL DEVELOPMENT CO LTD - CN104016979, 2017, B Location in patent: Paragraph 0637; 0638; 0639
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2021/87181, 2021, A1 Location in patent: Page/Page column 146-147
[4]Current Patent Assignee: SINO BIOPHARMACEUTICAL LIMITED - EP3248968, 2017, A1 Location in patent: Paragraph 0141
[5]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2019/152419, 2019, A1 Location in patent: Paragraph 0335; 0337-0338
[6]Current Patent Assignee: MIRATI THERAPEUTICS, INC. - WO2020/219448, 2020, A1 Location in patent: Paragraph 0387-0388
[7]Current Patent Assignee: MILA MEDICAL SHARE LTD COMPANY; MIRATI THERAPEUTICS, INC. - WO2020/247475, 2020, A1 Location in patent: Paragraph 0328-0329
[8]Current Patent Assignee: PRAXIS BIOTECH LLC - WO2020/132661, 2020, A2 Location in patent: Paragraph 0292
[9]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2010/145202, 2010, A1 Location in patent: Page/Page column 36-37
[10]Current Patent Assignee: GLAXOSMITHKLINE PLC - WO2010/146105, 2010, A1 Location in patent: Page/Page column 94
[11]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - WO2009/87212, 2009, A2 Location in patent: Page/Page column 148
[12]Current Patent Assignee: CHEMOCENTRYX INC - US2021/2229, 2021, A1 Location in patent: Paragraph 0132; 0134
  • 6
  • [ 893566-72-8 ]
  • [ 1171039-42-1 ]
  • [ 1171042-32-2 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate In 1,2-dimethoxyethane at 90℃; Inert atmosphere of argon; Microwave radiation; 2.129 To a solution of 6-(4,4,5,5-Tetramethyl-[l,3,2]dioxaborolan-2-yl)-3,4-dihydro-lH- isoquinoline-2-carboxylic acid tert-butylester (Intermediate B26) (3 eq, 0.960 mmol, 0.344 g) in dry DME (1 ml) under an inert atmosphere of argon is added 2M Na2COs (2 eq, 0.640 mmol, 0.32 ml) followed by (5"-Bromo-[2,2';4',3"]terpyridin-6'-yl)- cyclopropyl-amine (Example 1.26) (1 eq, 0.320 mmol, lOOmg) and PdCl2dppf (0.1 eq, 0.032 mmol, 23 mg). The reaction mixture is heated using microwave radiation at 90° C for 2 hours. The reaction mixture is dissolved in DCM and washed with water. The organic solvent is reduced in vacuo and the residue is purified by reverse phase column chromatography (Isolute Cl 8, 0-40% acetonitrile in water - 0.1% TFA). The appropriate fractions by HPLC are combined and concentrated in vacuo. The resulting residue is dissolved in MeOH and loaded onto a SCX-2 cartridge eluting with MeOH followed by 2M NH3 in MeOH. The methanolic ammonia fractions are combined, concentrated in vacuo and dried under vacuum to afford the title compound; [M+H]+ 420.
  • 7
  • [ 158984-84-0 ]
  • [ 893566-72-8 ]
YieldReaction ConditionsOperation in experiment
V.20 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate Example V-20 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate The title compound was prepared from 1,1-dimethylethyl 6-[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Example V-16) according to the procedure described in Example V-18. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (s, 12H), 1.42 (s, 9H), 2.78 (t, J=6.1 Hz, 2H), 3.54 (t, J=6.0 Hz, 2H), 4.50 (br. s., 2H), 7.16 (d, J=7.8 Hz, 1H), 7.45 (d, J=1.4 Hz, 2H).
V.20 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate Example V-20 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate The title compound was prepared from 1,1-dimethylethyl 6-[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Example V-16) according to the procedure described in Example V-18. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.28 (s, 12H), 1.42 (s, 9H), 2.78 (t, J=6.1 Hz, 2H), 3.54 (t, J=6.0 Hz, 2H), 4.50 (br. s., 2H), 7.16 (d, J=7.8 Hz, 1H), 7.45 (d, J=1.4 Hz, 2H).
  • 8
  • 5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]-benzonitrile [ No CAS ]
  • [ 893566-72-8 ]
  • [ 1258440-75-3 ]
YieldReaction ConditionsOperation in experiment
50% With sodium carbonate In 1,4-dioxane; water at 90℃; for 5h; Inert atmosphere; 26 A suspension of 5-(5-bromo-1,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (Preparation 11) (497 mg, 1.534 mmol) and 1,1-dimethylethyl 6-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 25) (580 mg, 1.614 mmol) in 1,4-dioxane (6 ml) and a saturated Na2CO3 aqueous solution (1.5 ml) was de-gassed under vacuum (ca 15 mbar) then flushed with nitrogen. 1,1'-bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex (118 mg, 0.161 mmol) was added. The resulting mixture was de-gassed under vacuum and flushed with nitrogen, stirred at 900C under nitrogen for 5 hours then cooled to room temperature and diluted with a saturated Na2CO3 aqueous solution and AcOEt. The insoluble material was filtered off and the layers were separated. The aqueous phase was extracted twice with AcOEt and the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (c- Hexane/AcOEt: 5 to 50% gradient) gave 1 ,1-dimethylethyl 6-(5-{3-cyano-4-[(1- methylethyl)oxy]phenyl}-1,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1H)- isoquinolinecarboxylate (386 mg, 50%) as a yellow solid LCMS: retention time 1.42 min; [M+H]+ = 477.0
With sodium hydrogencarbonate In 1,4-dioxane at 90℃; for 5h; Inert atmosphere; 5-(5-Bromo-1 ,3,4-thiadiazol-2-yl)-2-[(1-methylethyl)oxy]benzonitrile (Preparation 2) (500mg, 1.5 mmol) and 1 ,1-dimethylethyl 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl)-3,4-dihydro-2(1 H)-isoquinolinecarboxylate (Preparation 63) (580mg, 1.6 mmol) were suspended in 1 ,4-dioxane (6ml) and saturated sodium hydrogen carbonate solution (1.5ml, 1.6 mmol) under nitrogen. The reaction mixture was degassed, 1 ,1'- bis(diphenylphosphino)ferrocenedichloro palladium(ll) dichloromethane complex (120mg, 0.16 mmol) added and the mixture degassed again. The reaction was heated at 900C under nitrogen for 5h, cooled to room temperature and quenched with saturated sodium hydrogen carbonate solution. The mixture was diluted with ethyl acetate (10ml) and filtered to remove solids. The aqueous phase was extracted with ethyl acetate (2x 25ml), the combined organics washed with saturated brine, dried (MgSO4) and evaporated to give a dark brown oil which was stored under vacuum overnight. The residue was purified by chromatography on a silica cartridge, eluting with an ethyl acetate / hexane gradient (5-50%). The desired fractions were combined and evaporated to give 1 ,1-dimethylethyl 6-(5-{3-cyano-4-[(1- methylethyl)oxy]phenyl}-1 ,3,4-thiadiazol-2-yl)-3,4-dihydro-2(1 H)- isoquinolinecarboxylate as a yellow solid (390mg).LCMS (Method formate): Retention time 1.42min, MH+ = 477
  • 9
  • [ 24424-99-5 ]
  • [ 893566-72-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / methanol / 20 °C / Inert atmosphere 2.1: 1,1'-bis-(diphenylphosphino)ferrocene; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 0.08 h / 20 °C / Inert atmosphere 2.2: 4 h / 90 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane; ethyl acetate; tetrahydrofuran 2: triethylamine; Tf2O / dichloromethane
Multi-step reaction with 2 steps 1: dmap / tetrahydrofuran / 3 h / 25 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: dmap / tetrahydrofuran / 3 h / 25 °C 2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: triethylamine / methanol / 20 °C 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 80 °C / Inert atmosphere

  • 10
  • [ 893566-72-8 ]
  • [ 1258440-17-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere
  • 11
  • [ 893566-72-8 ]
  • [ 1258852-58-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 5 h / 90 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 3: silica gel / acetonitrile / 6 h / 60 °C / Inert atmosphere
  • 12
  • [ 215798-19-9 ]
  • [ 893566-72-8 ]
  • 13
  • [ 22246-12-4 ]
  • [ 893566-72-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 2-(3-methoxyphenyl)-1-ethanamine 2: triethylamine / dichloromethane; ethyl acetate; tetrahydrofuran 3: triethylamine; Tf2O / dichloromethane
  • 14
  • [ 59839-23-5 ]
  • [ 893566-72-8 ]
  • 15
  • [ 158984-83-9 ]
  • [ 893566-72-8 ]
  • 16
  • [ 893566-74-0 ]
  • [ 893566-72-8 ]
YieldReaction ConditionsOperation in experiment
With nitrogen 1.3 Preparation of the Compound of Formula (I) Step 3 Bis(pinacolato)diboron (975 g) and KOAc (940 g) were added to a solution of N-tert-butoxycarbonyl-6bromo-1,2,3,4-tetrahydroisoquinoline (1 kg) in dioxane (10 L) under the protection of nitrogen at 25° C., to which the catalyst Pd(dppf)Cl2 (13 g) was subsequently added. The mixture was stirred at 25° C. for 10 min, and then heated to 80° C. and stirred for 12 hours. After the reaction was completed, the mixture was filtered through diatomite put on Buchner funnel, rinsed with ethyl acetate (2.5 L*2), and the filtrate was concentrated to give N-tert-butoxycarbonyl-6-(4,4,5,5tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,4-tetrahydroisoquinoline (2.04 kg, crude product, purity of 85%) as a black crude oil, which was directly used in the next step. m/z 304 [M+H-56]+.
  • 17
  • 5-bromo-3-[1 (R)-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine [ No CAS ]
  • [ 893566-72-8 ]
  • [ 1613147-78-6 ]
YieldReaction ConditionsOperation in experiment
43.8% With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 85℃; for 10h; Inert atmosphere; 13.3 Step 3) (R)-5-(2-(tert-butoxycarbonyl)-1,2,3,4- tetrahydroisoquinolin-6-yl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-2-amine To a solution of (R)-5-bromo-3-(l-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine- 2-amine (246 mg, 0.65 mmol) and 2-(/er/-butoxycarbonyl)-6-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-l,2,3,4-tetrahydroisoquinoline (0.2 g, 0.56 mmol) in DME (5 mL) were added a solution of Na2C03 (0.19 g, 1.79 mmol) in H20 (1 mL) and Pd(PPh3)2Cl2 (62 mg, 0.088 mmol) under N2 atmosphere. The reaction was heated at 85 °C for 10 h, then cooled to rt, and diluted with EtOAc (10 mL). The mixture was filtered through a pad of Celite, which was washed with EtOAc (20 mL). The filtrate was washed with brine (10 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (v/v) = 2/1) to give the title compound as a yellow solid (0.13 g, 43.8%). NMR (400 MHz, CDC13) δ (ppm): 7.84-7.83 (d, J = 1.76 Hz, 1H,), 7.32-7.28 (m, 2H), 7.19- 7.18 (m, 1H), 7.13-7.12 (d, J = 5.7 Hz, 2H), 7.08-7.04 (m, 1H), 6.98-6.98 (d, J= 1.6 Hz, 1H), 6.14-6.09 (q, J = 6.6 Hz, 1H), 4.95 (s, 2H), 4.58 (s, 2H), 3.66 (s, 2H), 1.88-1.86 (d, J = 6.6 Hz, 2H), 1.96 (s, 9H).
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tert-Butyl 5-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 1.00

Chemical Structure| 1020174-05-3

[ 1020174-05-3 ]

Benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Structure| 1035235-26-7

[ 1035235-26-7 ]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 0.97

Chemical Structure| 893566-73-9

[ 893566-73-9 ]

tert-Butyl 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Related Parent Nucleus of
[ 893566-72-8 ]

Tetrahydroisoquinolines

Chemical Structure| 937048-76-5

[ 937048-76-5 ]

tert-Butyl 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 1.00

Chemical Structure| 1020174-05-3

[ 1020174-05-3 ]

Benzyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

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Chemical Structure| 1035235-26-7

[ 1035235-26-7 ]

tert-Butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate

Similarity: 0.97