Name: 1225380-05-1|1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene|95%
Brand: Ambeed
SKU: A310807
Rating: 95 (40 reviews)

1
[ 557-21-1 ]
[ 1225380-05-1 ]
[ 1225380-06-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	1A.4 3.34 g (12.50 mmol) of the compound obtained in Example 1A/step 3 were initially introduced into 2.5 ml of degassed DMF under argon, 881 mg (7.50 mmol) of zinc cyanide and 867 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 80° C. overnight. After cooling to RT, the reaction mixture was diluted with ethyl acetate and solid constituents were filtered off. The filtrate was washed twice with 2 N aqueous ammonia solution and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and freed from the solvent on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 85:15). 2.08 g (78% of th.) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, δ/ppm): 7.68 (d, 2H), 7.62 (d, 2H), 1.60 (s, 6H).GC/MS (method K, EI): Rt=3.83 min, m/z=213 [M]+.
78%	In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	1A.4 Step 4: 4-(1,1,1-Trifluoro-2-methylpropan-2-yl)benzenecarbonitrile; 3.34 g (12.50 mmol) of the compound obtained in Example 1A/step 3 were initially introduced into 2.5 ml of degassed DMF under argon, 881 mg (7.50 mmol) of zinc cyanide and 867 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 80° C. overnight. After cooling to RT, the reaction mixture was diluted with ethyl acetate and solid constituents were filtered off. The filtrate was washed twice with 2 N aqueous ammonia solution and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and freed from the solvent on a rotary evaporator. The residue was purified by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 85:15). 2.08 g (78% of theory) of the title compound were obtained.1H-NMR (400 MHz, CDCl3, δ/ppm): 7.68 (d, 2H), 7.62 (d, 2H), 1.60 (s, 6H).GC/MS (method I, EI): Rt=3.83 min, m/z=213 [M]+.
78%	In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	3A.4 3.34 g (12.50 mmol) of the compound obtained in Example 3A/Step 3 were initially charged in 2.5 ml of degassed DMF under argon, 881 mg (7.50 mmol) of zinc cyanide and 867 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was stirred at 80° C. overnight. After cooling to RT, the reaction mixture was diluted with ethyl acetate and solid constituents were filtered off. The filtrate was washed twice with 2 N aqueous ammonia solution and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and freed of the solvent on a rotary evaporator. The residue was purified by column chromatography on silica gel (eluent: 85:15 cyclohexane/ethyl acetate). 2.08 g (78% of theory) of the title compound were obtained.1H NMR (400 MHz, CDCl3, δ/ppm): 7.68 (d, 2H), 7.62 (d, 2H), 1.60 (s, 6H).GC/MS (method 9, ESIpos): Rt=3.83 min, m/z=213 [M]+.

78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	1A.4 Step 4: 4-(1,1,1-Trifluoro-2-methylpropan-2-yl)benzenecarbonitrile 3.34 g (12.50 mmol) of the compound obtained in Example 1A/step 3 were initially introduced into 2.5 ml of degassed DMF under argon, 881 mg (7.50 mmol) of zinc cyanide and 867 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 80° C. overnight. After cooling to RT, the reaction mixture was diluted with ethyl acetate and solid constituents were filtered off. The filtrate was washed twice with 2 N aqueous ammonia solution and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and freed from the solvent on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 85:15). 2.08 g (78% of th.) of the title compound were obtained. 1H-NMR (400 MHz, CDCl3, δ/ppm): 7.68 (d, 2H), 7.62 (d, 2H), 1.60 (s, 6H). GC/MS (method L, EI): Rt=3.83 min, m/z=213 [M]+.
78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;
78%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In N,N-dimethyl-formamide at 80℃; Inert atmosphere;	8.A.4 4-(1,1,1-Trifluoro-2-methylpropan-2-yl)benzenecarbonitrile 3.34 g (12.50 mmol) of the compound obtained in Example 8A/step 3 were initially introduced into 2.5 ml of degassed DMF under argon, 881 mg (7.50 mmol) of zinc cyanide and 867 mg (0.75 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at 80° C. overnight. After cooling to RT, the reaction mixture was diluted with ethyl acetate and solid constituents were filtered off. The filtrate was washed twice with 2 N aqueous ammonia solution and once with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulphate and freed from the solvent on a rotary evaporator. The residue was purified by column chromatography over silica gel (mobile phase: cyclohexane/ethyl acetate 85:15). This gave 2.08 g (78% of theory) of the title compound. 1H NMR (400 MHz, CDCl3, δ/ppm): 7.68 (d, 2H), 7.62 (d, 2H), 1.60 (s, 6H). GC/MS (Method 9, EIpos): Rt=3.83 min, m/z=213 [M]+.

Reference： [1]Current Patent Assignee: BAYER AG - US2011/301122, 2011, A1 Location in patent: Page/Page column 29
[2]Current Patent Assignee: BAYER AG - US2011/312930, 2011, A1 Location in patent: Page/Page column 33
[3]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1 Location in patent: Page/Page column 15
[4]Current Patent Assignee: BAYER AG - US2013/196964, 2013, A1 Location in patent: Paragraph 0800; 0801; 0802; 0803
[5]Haerter, Michael; Thierauch, Karl-Heinz; Boyer, Stephen; Bhargava, Ajay; Ellinghaus, Peter; Beck, Hartmut; Greschat-Schade, Susanne; Hess-Stumpp, Holger; Unterschemmann, Kerstin [ChemMedChem, 2014, vol. 9, # 1, p. 61 - 66]
[6]Current Patent Assignee: BAYER AG - US2014/329797, 2014, A1 Location in patent: Paragraph 0497; 0498; 0499; 0500

2
[ 16184-89-7 ]
[ 1225380-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: dichloromethane; n-heptane / 2.08 h / -40 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C 3.1: dichloromethane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: titanium tetrachloride / dichloromethane; n-heptane / 2.08 h / -40 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C 3.1: dichloromethane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: dichloromethane; n-heptane / -40 - 20 °C 1.2: Cooling with ice 2.1: sodium hydride / tetrahydrofuran; mineral oil / 20 - 40 °C / Inert atmosphere 2.2: 40 °C 3.1: dichloromethane / 0 - 20 °C

	Multi-step reaction with 3 steps 1.1: titanium tetrachloride / dichloromethane; n-heptane / 0.5 h / -30 °C 1.2: 2 h / -40 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C 3.1: dichloromethane; n-heptane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: titanium tetrachloride / n-heptane; dichloromethane / 0.5 h / -30 °C 1.2: 2.08 h / -40 - 20 °C 2.1: sodium hydride / mineral oil; tetrahydrofuran / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C / Inert atmosphere 3.1: dichloromethane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: dichloromethane / 2.08 h / -40 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C / Inert atmosphere 3.1: dichloromethane; n-heptane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: titanium tetrachloride / dichloromethane / 2 h / -40 - 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 2.2: 1 h / 40 °C 3.1: dichloromethane / 1.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: BAYER AG - US2011/301122, 2011, A1
[2]Current Patent Assignee: BAYER AG - US2011/312930, 2011, A1
[3]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1
[4]Current Patent Assignee: BAYER AG - US2013/150325, 2013, A1
[5]Current Patent Assignee: BAYER AG - US2013/196964, 2013, A1
[6]Haerter, Michael; Thierauch, Karl-Heinz; Boyer, Stephen; Bhargava, Ajay; Ellinghaus, Peter; Beck, Hartmut; Greschat-Schade, Susanne; Hess-Stumpp, Holger; Unterschemmann, Kerstin [ChemMedChem, 2014, vol. 9, # 1, p. 61 - 66]
[7]Current Patent Assignee: BAYER AG - US2014/329797, 2014, A1

3
[ 1225380-04-0 ]
[ 75-24-1 ]
[ 1225380-05-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	In dichloromethane at 0 - 20℃; for 1.5h;	1A.3 12.4 g (35.72 mmol) of the compound obtained in Example 1A/step 2 were initially introduced into 250 ml of methylene chloride and the mixture was cooled to 0° C. 35.7 ml (71.44 mmol) of a 2 M solution of trimethylaluminium were then slowly added dropwise at 0° C., while stirring, and the mixture was then allowed to come to RT and was subsequently stirred at RT for a further 1.5 h. 120 ml of a saturated aqueous sodium bicarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of a saturated aqueous sodium chloride solution. The mixture was filtered over kieselguhr and the kieselguhr was rinsed twice with methylene chloride. The combined methylene chloride phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulphate and the solvent was removed on a rotary evaporator. 8.69 g (87% of th.) of the title compound were obtained in a purity of 95%.1H-NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H).LC/MS (method E, ESIpos): Rt=2.54 min, no ionization.GC/MS (method K, EI): Rt=3.48 min, m/z=266 [M]+.
87%	In dichloromethane at 0 - 20℃; for 1.5h;	1A.3 Step 3: 1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene; 12.4 g (35.72 mmol) of the compound obtained in Example 1A/step 2 were initially introduced into 250 ml of dichloromethane and the mixture was cooled to 0° C. 35.7 ml (71.44 mmol) of a 2 M solution of trimethylaluminium were then slowly added dropwise at 0° C., while stirring, and the mixture was then allowed to come to RT and was subsequently stirred at RT for a further 1.5 h. 120 ml of a saturated aqueous sodium bicarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of a saturated aqueous sodium chloride solution. The mixture was filtered over kieselguhr and the kieselguhr was rinsed twice with dichloromethane. The combined dichloromethane phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulphate and the solvent was removed on a rotary evaporator. 8.69 g (87% of theory) of the title compound were obtained in a purity of 95%.1H-NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H).LC/MS (method E, ESIpos): Rt=2.54 min, no ionization.GC/MS (method I, EI): Rt=3.48 min, m/z=266 [M]+.
87%	In dichloromethane at 0 - 20℃;	3A.3 12.4 g (35.72 mmol) of the compound obtained in Example 3A/Step 2 were initially charged in 250 ml of dichloromethane and the mixture was cooled to 0° C. Then 35.7 ml (71.44 mmol) of a 2 M solution of trimethylaluminium were slowly added dropwise at 0° C. while stirring, then the mixture was allowed to come to RT and stirred at RT for a further 1.5 h. 120 ml of saturated aqueous sodium hydrogencarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of saturated aqueous sodium chloride solution. The mixture was filtered through kieselguhr and the kieselguhr was washed again twice with dichloromethane. The combined dichloromethane phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulphate, and the solvent was removed on a rotary evaporator. 8.69 g (87% of theory) of the title compound were obtained in a purity of 95%.1H NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H).GC/MS (method 9, ESIpos): Rt=3.48 min, m/z=266 [M]+.

87%	In n-heptane; dichloromethane at 0 - 20℃; for 1.5h;	7A.3 Step 3: 1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene Step 3: 1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene 12.4 g (35.72 mmol) of the compound obtained in Example 7A/Step 2 were initially charged in 250 ml of dichloromethane, and the mixture was cooled to 0° C. With stirring, 35.7 ml (71.4 mmol) of a 2 M solution of trimethylaluminium in heptane were slowly added dropwise at 0° C., and the mixture was then allowed to warm to RT and stirred at RT for a further 1.5 h. 120 ml of a saturated aqueous sodium bicarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of a saturated aqueous sodium chloride solution. The mixture was filtered through kieselguhr and the kieselguhr was washed twice with dichloromethane. The combined dichloromethane phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulphate, and the solvent was removed on a rotary evaporator. This gave 8.69 g (87% of theory) of the title compound in a purity of 95%. 1H NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H). LC/MS (Method 4, ESIpos): Rt=2.54 min, no ionization. GC/MS (Method 10, EIpos): Rt=3.48 min, m/z=266 [M]+.
87%	In dichloromethane at 0 - 20℃; for 1.5h;	1A.3 Step 3: 1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene 12.4 g (35.72 mmol) of the compound obtained in Example 1A/step 2 were initially introduced into 250 ml of methylene chloride and the mixture was cooled to 0° C. 35.7 ml (71.44 mmol) of a 2 M solution of trimethylaluminium were then slowly added dropwise at 0° C., while stirring, and the mixture was then allowed to come to RT and was subsequently stirred at RT for a further 1.5 h. 120 ml of a saturated aqueous sodium bicarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of a saturated aqueous sodium chloride solution. The mixture was filtered over kieselguhr and the kieselguhr was rinsed twice with methylene chloride. The combined methylene chloride phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate and the solvent was removed on a rotary evaporator. 8.69 g (87% of th.) of the title compound were obtained in a purity of 95%. 1H-NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H). LC/MS (method E, ESIpos): Rt=2.54 min, no ionization. GC/MS (method L, EI): Rt=3.48 min, m/z=266 [M]+.
87%	In n-heptane; dichloromethane at 0 - 20℃; for 1.5h;
87%	In dichloromethane at 0 - 20℃; for 1.5h;	8.A.3 1-Bromo-4-(1,1,1-trifluoro-2-methylpropan-2-yl)benzene 12.4 g (35.72 mmol) of the compound obtained in Example 8A/step 2 were initially introduced into 250 ml of dichloromethane and the mixture was cooled to 0° C. 35.7 ml (71.44 mmol) of a 2 M solution of trimethylaluminium were then slowly added dropwise at 0° C., while stirring, and the mixture was then allowed to come to RT and was subsequently stirred at RT for a further 1.5 h. 120 ml of saturated aqueous sodium hydrogencarbonate solution were slowly added dropwise to the mixture, followed by 40 ml of saturated aqueous sodium chloride solution. The mixture was filtered through kieselguhr and the kieselguhr was washed again twice with dichloromethane. The combined dichloromethane phases were washed once with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulphate, and the solvent was removed on a rotary evaporator. This gave 8.69 g (87% of theory) of the title compound in a purity of 95%. 1H NMR (400 MHz, CDCl3, δ/ppm): 7.49 (d, 2H), 7.33 (d, 2H), 1.55 (s, 6H). GC/MS (Method 9, EIpos): Rt=3.48 min, m/z=266 [M]+.

Reference： [1]Current Patent Assignee: BAYER AG - US2011/301122, 2011, A1 Location in patent: Page/Page column 29
[2]Current Patent Assignee: BAYER AG - US2011/312930, 2011, A1 Location in patent: Page/Page column 33
[3]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1 Location in patent: Page/Page column 15
[4]Current Patent Assignee: BAYER AG - US2013/150325, 2013, A1 Location in patent: Paragraph 0456; 0457; 0458; 0459; 0460
[5]Current Patent Assignee: BAYER AG - US2013/196964, 2013, A1 Location in patent: Paragraph 0795; 0796; 0797; 0798; 0799
[6]Haerter, Michael; Thierauch, Karl-Heinz; Boyer, Stephen; Bhargava, Ajay; Ellinghaus, Peter; Beck, Hartmut; Greschat-Schade, Susanne; Hess-Stumpp, Holger; Unterschemmann, Kerstin [ChemMedChem, 2014, vol. 9, # 1, p. 61 - 66]
[7]Current Patent Assignee: BAYER AG - US2014/329797, 2014, A1 Location in patent: Paragraph 0493; 0494; 0495; 0496

4
[ 122243-28-1 ]
[ 1225380-05-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 1.2: 1 h / 40 °C 2.1: dichloromethane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 20 - 40 °C / Inert atmosphere 1.2: 40 °C 2.1: dichloromethane / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 1.2: 1 h / 40 °C 2.1: dichloromethane; n-heptane / 1.5 h / 0 - 20 °C

	Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 1.5 h / 20 - 40 °C / Inert atmosphere 1.2: 1 h / 40 °C / Inert atmosphere 2.1: dichloromethane / 1.5 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 20 - 40 °C / Inert atmosphere 1.2: 1 h / 40 °C 2.1: dichloromethane / 1.5 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: BAYER AG - US2011/301122, 2011, A1 Current Patent Assignee: BAYER AG - US2011/312930, 2011, A1
[2]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1
[3]Current Patent Assignee: BAYER AG - US2013/150325, 2013, A1
[4]Current Patent Assignee: BAYER AG - US2013/196964, 2013, A1
[5]Current Patent Assignee: BAYER AG - US2014/329797, 2014, A1

5
[ 1225380-05-1 ]
[ 1225380-03-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: hydroxylamine hydrochloride; triethylamine / ethanol / 1 h / Reflux
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: triethylamine / ethanol / 1 h / Reflux
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: hydroxylamine hydrochloride; triethylamine / ethanol / 1 h / Reflux

	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: triethylamine; hydroxylamine hydrochloride / ethanol / 1 h / Reflux
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: hydroxylamine hydrochloride; triethylamine / ethanol / 1 h / Reflux

Reference： [1]Current Patent Assignee: BAYER AG - US2011/301122, 2011, A1 Current Patent Assignee: BAYER AG - US2011/312930, 2011, A1
[2]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1
[3]Current Patent Assignee: BAYER AG - US2013/196964, 2013, A1
[4]Haerter, Michael; Thierauch, Karl-Heinz; Boyer, Stephen; Bhargava, Ajay; Ellinghaus, Peter; Beck, Hartmut; Greschat-Schade, Susanne; Hess-Stumpp, Holger; Unterschemmann, Kerstin [ChemMedChem, 2014, vol. 9, # 1, p. 61 - 66]
[5]Current Patent Assignee: BAYER AG - US2014/329797, 2014, A1

6
[ 1225380-05-1 ]
[ 1225380-24-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere 2: triethylamine / ethanol / 1 h / Reflux 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h / 20 - 140 °C
	Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere 2: triethylamine; hydroxylamine hydrochloride / ethanol / 1 h / Reflux 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 7 h / 20 - 140 °C

Reference： [1]Current Patent Assignee: BAYER AG - US2012/28950, 2012, A1
[2]Haerter, Michael; Thierauch, Karl-Heinz; Boyer, Stephen; Bhargava, Ajay; Ellinghaus, Peter; Beck, Hartmut; Greschat-Schade, Susanne; Hess-Stumpp, Holger; Unterschemmann, Kerstin [ChemMedChem, 2014, vol. 9, # 1, p. 61 - 66]

7
[ 1225380-05-1 ]
[ 1418295-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / 0 - 5 °C / Inert atmosphere 1.2: 0 - 10 °C 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / 0 - 5 °C 3.1: hydrogenchloride / 1,4-dioxane / 20 °C 4.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; XPhos / N,N-dimethyl-formamide / 16 h / 20 - 80 °C / Inert atmosphere