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Chemical Structure| 179894-36-1

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Product Details of [ 179894-36-1 ]

CAS No. :179894-36-1
Formula : C17H24BNO4
M.W : 317.19
SMILES Code : CC1=CC(C)(C)N(C(OC(C)(C)C)=O)C2=C1C=C(B(O)O)C=C2
MDL No. :MFCD13248580

Safety of [ 179894-36-1 ]

Application In Synthesis of [ 179894-36-1 ]

* 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 [ 179894-36-1 ]

[ 179894-36-1 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 13195-50-1 ]
  • [ 179894-36-1 ]
  • 2,2,4-trimethyl-6-(5-nitro-thiophen-2-yl)-2<i>H</i>-quinoline-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 2
  • [ 18791-99-6 ]
  • [ 179894-36-1 ]
  • 6-(5-cyano-thiophen-3-yl)-2,2,4-trimethyl-2<i>H</i>-quinoline-1-carboxylic acid <i>tert</i>-butyl ester [ No CAS ]
  • 3
  • [ 18791-99-6 ]
  • [ 179894-36-1 ]
  • LG121046 [ No CAS ]
YieldReaction ConditionsOperation in experiment
160 mg (91%) 6-(5-Cyano-3-thienyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 452) This compound was prepared by General Method 2 from compound 9 (200 mg, 0.63 mmol) and <strong>[18791-99-6]4-bromo-2-cyanothiophene</strong> (0.50 g, 2.65 mmol). The crude product was purified by prep. TLC (20*20 cm, 1000 mum, 25% ETOAc:Hexane) to afford 160 mg (91%) of Compound 452 as a yellow oil. Data for Compound 452: Rf 0.50 (silica gel, 25% EtOAc:hex); 1 H NMR(400 MHz, CDCl3) 7.79 (s, 1 H), 7.46 (s, 1 H), 7.20 (s, 1 H), 7.16 (d, J=8.3, 1 H), 6.46 (d, J=8.3, 1 H), 5.37 (s, 1 H), 2.03 (s, 3 H), 1.31 (s, 6H); IR(film, NaCl) 1159, 1381, 1402, 1449, 1476, 1499, 1609, 1653, 2216, 2915, 3294, 3584.
160 mg (91%) 6-(5-Cyano-3-thienyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 452). This compound was prepared by General Method 2 from compound 9 (200 mg, 0.63 mmol) and <strong>[18791-99-6]4-bromo-2-cyanothiophene</strong> (0.50 g, 2.65 mmol). The crude product was purified by prep. TLC (20*20 cm, 1000 mum, 25% ETOAc:Hexane) to afford 160 mg (91%) of Compound 452 as a yellow oil. Data for Compound 452:Rf 0.50 (silica gel, 25% EtOAc:hex); 1 H NMR(400 MHz, CDCl3) 7.79 (s, 1H), 7.46 (s, 1H), 7.20 (s, 1H), 7.16 (d, J=8.3, 1H), 6.46 (d, J=8.3, 1H), 5.37 (s, 1H), 2.03 (s, 3H), 1.31 (s, 6H); IR (film, NaCl) 1159, 1381, 1402, 1449, 1476, 1499, 1609, 1653, 2216, 2915, 3294, 3584.
160 mg (91%) 6-(5-Cyano-3-thienyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 452) This compound was prepared by General Method 2 from compound 9 (200 mg, 0.63 mmol) and <strong>[18791-99-6]4-bromo-2-cyanothiophene</strong> (0.50 g, 2.65 mmol). The crude product was purified by prep. TLC (20*20 cm, 1000 mum, 25% ETOAc:Hexane) to afford 160 mg (91%) of Compound 452 as a yellow oil. Data for Compound 452: Rf 0.50 (silica gel, 25% EtOAc:hex); 1 H NMR(400 MHz, CDCl3) 7.79 (s, 1H), 7.46 (s, 1H), 7.20 (s, 1H), 7.16 (d, J=8.3, 1H), 6.46 (d, J=8.3, 1H), 5.37 (s, 1H), 2.03 (s, 3H), 1.31 (s, 6H); IR (film, NaCl) 1159, 1381, 1402, 1449, 1476, 1499, 1609, 1653, 2216, 2915, 3294, 3584.
  • 4
  • [ 13195-50-1 ]
  • [ 179894-36-1 ]
  • 1,2-Dihydro-2,2,4-trimethyl-6-(5-nitro-thien-2-yl)quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
50 mg (81%) EXAMPLE 200 1,2-Dihydro-2,2,4-trimethyl-6-(5-nitro-2-thienyl)quinoline (Compound 300, structure 4 of Scheme II, where R1 =5-nitro-2-thienyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.16 mmol) and <strong>[13195-50-1]2-bromo-5-nitrothiophene</strong> (0.16 g, 0.79 mmol). The crude product was purified by prep TLC (20*20 cm, 1000 mm, 25percent EtOAc:hexane) to afford 50 mg (81percent) of Compound 300 as a purple solid. Data for compound 300: Rf=0.40 (silica gel, 25percent EtOAc:hex); 1 H NMR (400 MHz, CDCl3) 7.85 (d, J=4.3, 1H), 7.27 (m, 2H), 7.04 (d, J=4.3, 1H), 6.43 (d, J=8.5, 1H), 5.38 (brs, 1H), 4.13 (brs, 1H), 2.03 (s, 3H), 1.32 (s, 6H).
50 mg (81%) EXAMPLE 200 1,2-Dihydro-2,2,4-trimethyl-6-(5-nitro-2-thienyl)quinoline (Compound 300, Structure 4 of Scheme II, where R1 =5-nitro-2-thienyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.16 mmol) and <strong>[13195-50-1]2-bromo-5-nitrothiophene</strong> (0.16 g, 0.79 mmol). The crude product was purified by prep TLC (20*20 cm, 1000 mm, 25percent EtOAc:hexane) to afford 50 mg (81percent) of Compound 300 as a purple solid. Data for compound 300: Rf=0.40 (silica gel, 25percent EtOAc:hex); 1 H NMR (400 MHz, CDCl3) 7.85 (d, J=4.3, 1 H), 7.27 (m, 2 H), 7.04 (d, J=4.3, 1 H), 6.43 (d, J=8.5, 1 H), 5.38 (brs, 1 H), 4.13 (brs, 1 H), 2.03 (s, 3 H), 1.32 (s, 6H).
50 mg (81%) EXAMPLE 200 1,2-Dihydro-2,2,4-trimethyl-6-(5-nitro-2-thienyl)quinoline (Compound 300, structure 4 of Scheme II, where R1 =5-nitro-2-thienyl) This compound was prepared by General Method 2 (EXAMPLE 9) from Compound 9 (50 mg, 0.16 mmol) and <strong>[13195-50-1]2-bromo-5-nitrothiophene</strong> (0.16 g, 0.79 mmol). The crude product was purified by prep TLC (20*20cm, 1000 mm, 25percent EtOAc:hexane) to afford 50 mg (81percent) of Compound 300 as a purple solid.
  • 5
  • [ 38573-88-5 ]
  • [ 179894-36-1 ]
  • [ 179894-86-1 ]
YieldReaction ConditionsOperation in experiment
16 mg (62%) EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).
16 mg (62%) EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).
16 mg (62%) EXAMPLE 52 6-(2,3-Difluorophenyl)-1,2-dihydro-2,2,4-trimethylquinoline (Compound 152, structure 4 of Scheme II, where R1 =2,3-difluorophenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (28.7 mg, 0.09 mmol) and <strong>[38573-88-5]1-<strong>[38573-88-5]bromo-2,3-difluorobenzene</strong></strong> (10 muL, 0.09 mmol, Aldrich). The crude product was isolated and purified by silica gel chromatography (75 mL silica, 5percent ethyl acetate/hexane) to afford 16 mg (62percent) of Compound 152. Data for Compound 152: 1 H NMR (400 MHz, acetone-d6) 7.21 (m, 5H); 6.57 (d, J=8.3, 1 H); 5.37 (s, 1H); 1.99 (s, 3H); 1.28 (s, 6H).
  • 6
  • [ 130723-13-6 ]
  • [ 179894-36-1 ]
  • [ 179896-06-1 ]
YieldReaction ConditionsOperation in experiment
3.1 mg (7%) In methanol; EXAMPLE 174 6-[5-fluoro-3-(trifluoromethyl)phenyl]-1,2-dihydro-2,2,4-trimethylquinoline (Compound 274, structure 4 of Scheme II, where R1 =5-fluoro-3-(trifluoromethyl)phenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (42.8 mg, 0.13 mmol) and <strong>[130723-13-6]3-bromo-5-fluorobenzotrifluoride</strong> (32.7 mg, 0.13 mmol). The crude material was purified by HPLC (reverse phase ODS column, 90% methanol/water, 3.0 mL/min) to afford 3.1 mg (7%) of Compound 274. Data for Compound 274: 1 H NMR (400 MHz, acetone-d6) 7.71 (s, 1H), 7.63 (d, J=10.5. 1H), 7.40 (d, J=2.2, 1H), 7.34 (dd, J=8.1, 2.0, 1H), 7.29 (d, J=8.6, 1H), 6.59 (d, J=8.3, 1H), 5.50 (s, 1H), 5.39 (s, 1H), 2.5 (s, 3H), 1.29 (s, 6H).
3.1 mg (7%) In methanol; EXAMPLE 174 6-[5-fluoro-3-(trifluoromethyl)phenyl]-1,2-dihydro-2,2,4-trimethylquinoline (Compound 274, Structure 4 of Scheme II, where R1 =5-fluoro-3-(trifluoromethyl)phenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (42.8 mg, 0.13 mmol) and <strong>[130723-13-6]3-bromo-5-fluorobenzotrifluoride</strong> (32.7 mg, 0.13 mmol). The crude material was purified by HPLC (reverse phase ODS column, 90% methanol/water, 3.0 mL/min) to afford 3.1 mg (7%) of Compound 274. Data for Compound 274: 1 H NMR (400 MHz, acetone-d6) 7.71 (s, 1 H), 7.63 (d, J=10.5. 1 H), 7.40 (d, J=2.2, 1 H), 7.34 (dd, J=8.1, 2.0, 1 H), 7.29 (d, J=8.6, 1 H), 6.59 (d, J=8.3, 1 H), 5.50 (s, 1 H), 5.39 (s, 1 H), 2.05 (s, 3 H), 1.29 (s, 6 H).
3.1 mg (7%) In methanol; EXAMPLE 174 6-[5-fluoro-3-(trifluoromethyl)phenyl]-1,2-dihydro-2,2,4-trimethylquinoline (Compound 274, structure 4 of Scheme II, where R1 =5-fluoro-3-(trifluoromethyl)phenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (42.8 mg, 0.13 mmol) and <strong>[130723-13-6]3-bromo-5-fluorobenzotrifluoride</strong> (32.7 mg, 0.13 mmol). The crude material was purified by HPLC (reverse phase ODS column, 90% methanol/water, 3.0 mL/min) to afford 3.1 mg (7%) of Compound 274. Data for Compound 274: 1 H NMR (400 MHz, acetone-d6) 7.71 (s, 1H), 7.63 (d, J=10.5. 1H), 7.40 (d, J=2.2, 1H), 7.34 (dd, J=8.1, 2.0, 1H), 7.29 (d, J=8.6, 1H), 6.59 (d, J=8.3, 1H), 5.50 (s, 1H), 5.39 (s, 1H), 2.05 (s, 3H), 1.29 (s, 6H).
3.1 mg (7%) In methanol; EXAMPLE 174 6-[5-fluoro-3-(trifluoromethyl)phenyl]-1,2-dihydro-2,2,4-trimethylquinoline (Compound 274, structure 4 of Scheme II, where R1 =5-fluoro-3-(trifluoromethyl)phenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (42.8 mg, 0.13 mmol) and <strong>[130723-13-6]3-bromo-5-fluorobenzotrifluoride</strong> (32.7 mg, 0.13 mmol). The crude material was purified by HPLC (reverse phase ODS column, 90% methanol/water, 3.0 mL/min) to afford 3.1 mg (7%) of Compound 274. Data for Compound 274: 1 H NMR (400 MHz, acetone-d6) 7.71 (s, 1 H), 7.63 (d, J=10.5. 1 H), 7.40 (d, J=2.2, 1 H), 7.34 (dd, J=8.1, 2.0, 1 H), 7.29 (d, J=8.6, 1 H), 6.59 (d, J=8.3, 1 H), 5.50 (s, 1 H), 5.39 (s, 1 H), 2.05 (s, 3 H), 1.29 (s, 6 H).

  • 7
  • [ 130723-13-6 ]
  • [ 179894-36-1 ]
  • 6-›5-fluoro-3-(trifluoromethyl)phenyl-1,2-dihydro-2,2,4-trimethylquinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.1 mg (7%) In methanol; EXAMPLE 174 6-?5-fluoro-3-(trifluoromethyl)phenyl-1,2-dihydro-2,2,4-trimethylquinoline (Compound 274, structure 4 of Scheme II, where R1 =5-fluoro-3-(trifluoromethyl)phenyl) This compound was prepared according to General Method 2 (EXAMPLE 9) from Compound 9 (42.8 mg, 0.13 mmol) and <strong>[130723-13-6]3-bromo-5-fluorobenzotrifluoride</strong> (32.7 mg, 0.13 mmol). The crude material was purified by HPLC (reverse phase ODS column, 90% methanol/water, 3.0 mL/min) to afford 3.1 mg (7%) of Compound 274. Data for Compound 274: 1 H NMR (400 MHz, acetone-d6) 7.71 (s, 1H), 7.63 (d, J=10.5. 1H), 7.40 (d, J=2.2, 1H), 7.34 (dd, J=8.1, 2.0, 1H), 7.29 (d, J=8.6, 1H), 6.59 (d, J=8.3, 1H), 5.50 (s, 1H), 5.39 (s, 1H), 2.05 (s, 3H), 1.29 (s, 6H).
 

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