Name: 125328-80-5|N-(4-Bromo-3-chloro-2-methylphenyl)acetamide|98%
Brand: Ambeed
SKU: A209344
Price: 20.0 USD
Availability: InStock
Rating: 90 (25 reviews)

1
[ 7463-35-6 ]
[ 125328-80-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With bromine; acetic acid for 2h;
96%	With bromine In acetic acid at 15℃; for 2h;	4.4B To a suspension of acetamide 4A (2.00 g, 10.9 mmol) in 15 mL of glacialAcOH cooled to approximately15 C was added bromine (1.67mL, 32.7 mmol) over 20 min. The ice bath was removed and the solution was stirred for 2 h, poured into ice water with stirring, and the solid was then filtered and dried to give 2.75 g (96%) of the desiredbromide. 1H NMR (DMSO-d6) 8 2.05 (s, 3H), 2.28 (s, 3H), 7.29 (d,J= 8.3,1H), 7.56 (d,J= 8.8,1H), 9.60 (s,1H) ; 13C NMR(DMSO-d6) # 16.7, 23.1, 118.1, 125.5, 130.4, 132.7, 133.4, 137.1, 168.4 ; HPLC a) column: PhenominexODS C18 4.6 x 50 mm, 4 min gradient,, 10% MeOH/90%H20/0.1% TFA to90% MeOH/10% H2O/0. 1% TFA,1 min hold, 4mL/min, UV detection at 220nm, 2.95 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6 x 50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4mL/min, UV detection at 220 nm, 2.87 min retention time (98%); MS (ES)mAz 263 [M+H] +.
96%	With bromine; acetic acid at 0 - 15℃; for 2.33333h;	1B To a suspension of acetamide 1A (2.00 g, 10.9 mmol) in 15 mL of glacial AcOH cooled to approximately 15° C. was added bromine (1.67 mL, 32.7 mmol) over 20 min. The ice bath was removed and the solution was stirred for 2 h, poured into ice water with stirring, and the solid was then filtered and dried to give 2.75 g (96%) of the desired bromide. 1H NMR (DMSO-d6) δ 2.05 (s, 3H), 2.28 (s, 3H), 7.29 (d, J=8.3, 1H), 7.56 (d, J=8.8, 1H), 9.60 (s, 1H); 13C NMR (DMSO-d6) δ 16.7, 23.1, 118.1, 125.5, 130.4, 132.7, 133.4, 137.1, 168.4; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.95 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.87 min retention time (98%); MS (ES) m/z 263 [M+H]+.

96%	With bromine; acetic acid at 15℃; for 2.33h;	1.B 1B. 4-Bromo-3-chloro-2-methylphenylacetamide; To a suspension of acetamide 1A (2.0 g, 10.9 mmol) in 15 mL of glacial AcOH cooled to approximately 15° C. was added bromine (1.67 mL, 32.7 mmol) over 20 min. The ice bath was removed and the solution was stirred for 2 h, poured into ice water with stirring, and the solid was then filtered and dried to give 2.75 g (96%) of the desired bromide. 1H NMR (DMSO-d6) δ 2.05 (s, 3H), 2.28 (s, 3H), 7.29 (d, J=8.3, 1H), 7.56 (d, J=8.8, 1H), 9.60 (s, 1H); 13C NMR (DMSO-d6) δ 16.7, 23.1, 118.1, 125.5, 130.4, 132.7, 133.4, 137.1, 168.4; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.95 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.87 min retention time (98%); MS (ES) m/z 263 [M+H]+.
93.6%	With bromine; acetic acid at 0℃; for 17.5h;	24 N-(4-Bromo-3-chloro-2-methyl-phenyl)-acetamideDissolve N-(3-chloro-2-methyl-phenyl)-acetamide (120.0 g, 0.653 mol) in acetic acid and cool to 0 °C. Add bromine (313.3 g, 1.96 mol) dropwise over 30 min via an addition funnel. Stir for 17 h while allowing the reaction to warm to room temperature. Pour the reaction into IL of ice, and filter. Rinse the filter cake with 4L of water. The title product is isolated in 93.6% yield (160.6 g) as a white solid. MS: MS (ESI-): 262 (M-I)". MS (ESI+): 263 (M+l)+.
90%	With bromine In acetic acid at 0 - 20℃; for 24h;	b b) N-(4-bromo-3-chloro-2-methylphenyl)acetamide b) N-(4-bromo-3-chloro-2-methylphenyl)acetamideTo a suspension of N-(3-chloro-2-methylphenyl)acetamide (35 g, 0.19 mol) in 350 mL of glacial AcOH cooled to 0 °C was added bromine (29.5 mL, 0.57 mol) dropwise. The ice bath was removed and the solution was stirred for 24 h and then poured into ice water with stirring. The solid was then filtered and dried to give the title compound (45 g, 90%) which was used for the next step without any further purification.1H NMR (400 MHz, DMSO-d6): δ 9.60 (bs, 1 H), 7.58 (d, J = 8.8 Hz, 1 H), 7.30 (d, J = 8.7 Hz, 1 H), 2.29 (s, 3H), 2.06 (s, 3H); MS (ES): m/z 261 .9 (M + 1 ).
90%	With bromine; acetic acid at 0 - 20℃; for 24h;	A1.b b) N-(4-bromo-3-chloro-2-methylphenyl)acetamide To a suspension of N-(3-chloro-2-methylphenyl)acetamide (35 g, 0.19 mol) in 350 mL of glacial AcOH cooled to 0°C. was added bromine (29.5 mL, 0.57 mol) dropwise. The ice bath was removed and the solution was stirred for 24 h and then poured into ice water with stirring. The solid was then filtered and dried to give the title compound (45 g, 90%) which was used for the next step without any further purification. 1H NMR (400 MHz, DMSO-d6): δ 9.60 (bs, 1H), 7.58 (d, J=8.8 Hz, 1H), 7.30 (d, J=8.7 Hz, 1H), 2.29 (s, 3H), 2.06 (s, 3H); MS (ES): m/z 261.9 (M+1).
77.4%	With bromine; acetic acid at -5 - 0℃; for 4h;	1.2; 2.4 The second step is to dissolve 14 grams of bromine in 42 grams of glacial acetic acid and drop it into another three-necked flask (containing 3-chloro-2-methylacetanilide) at a rate of one drop per minute. Acetic acid solution), use an ice water bath to control the temperature in the three-necked flask between -5 0 , after 4 hours, the addition is complete, followed by TLC, after the reaction is completed, pour into 1000ml of ice water, stir,There is light yellow flocculent precipitation, filtering, drying,Recrystallization gave 23 g of white powdery solid. (The comprehensive yield of the first and second steps is 77.4%)
70%	With bromine; acetic acid at 0 - 20℃; for 4h;
	With bromine; nitrobenzene
	With bromine
	With bromine In acetic acid at 15 - 20℃; for 2.5h;	Step B: N-(4-bromo-3 -chloro-2-methylphenyl)acetamide Step B: N-(4-bromo-3 -chloro-2-methylphenyl)acetamideTo a solution of N-(3-chloro-2-methylphenyl)acetamide (13.00 g, 70.8 mmol) in AcOH (100 mL) was added Br2 (10.9 mL, 0.212 mol) at 15 °C dropwise over 30 mm. The solution was thenstirred at room temperature for 2 h. The mixture was poured into ice water and stirred, filtered and dried to afford the title compound. LC/MS [M+1] =262; 264. ‘H NIVIR (400 MHz, MeOD) 7.54-7.52 (d, J 8.8 Hz, 1H), 7.22-7.19 (d, J 8.4 Hz, 1H), 2.35 (s, 3H), 2.16 (s, 3H).
	With bromine; acetic acid for 14h;	20 A solution of N-(4-bromo-3-chloro-2-methyl-phenyl)-acetamide (10.00 g, 54.50 mmol) and Br2 (2.80 mL, 54.40 mmol) in HOAc was stirred for 14 hours. The resulting solution was then quenched in H2O and the precipitate was filtered. The precipitate was purified by column chromatography using hex:EtOAc (1:1) as the eluant to afford the title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3.) δ 2.19 (s, 3H), 2.35 (s, 3H), 7.06 (br s, 1H), 7.43-7.55 (m, 2H).

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2005/49580, 2005, A1 Location in patent: Page/Page column 43
[3]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/197367, 2005, A1 Location in patent: Page/Page column 17
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/4717, 2007, A1 Location in patent: Page/Page column 16-17
[5]Current Patent Assignee: ELI LILLY & CO - WO2006/124447, 2006, A2 Location in patent: Page/Page column 64
[6]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/14627, 2013, A1 Location in patent: Page/Page column 45; 46
[7]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2014/329876, 2014, A1 Location in patent: Paragraph 0429; 0432; 0433
[8]Current Patent Assignee: HUNAN HENGTAI BIOPHARMACEUTICAL - CN110683981, 2020, A Location in patent: Paragraph 0018; 0020
[9]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[10]Current Patent Assignee: BASF - DE217896, 1800, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 135][Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 10, p. 135]
[11]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]
[12]Current Patent Assignee: MERCK & CO INC - WO2016/8064, 2016, A1 Location in patent: Page/Page column 56
[13]Current Patent Assignee: ABBVIE INC - US2008/194650, 2008, A1 Location in patent: Page/Page column 24-25

2
[ 125328-80-5 ]
[ 544-92-3 ]
[ 627531-48-0 ]

Yield	Reaction Conditions	Operation in experiment
67%	In DMF (N,N-dimethyl-formamide) at 150℃; for 4h;	1C A suspension of bromide 1B (2.70 g, 10.3 mmol) and copper cyanide (0.92 g, 10.3 mmol) in DMF (30 mL) was heated to 150° C. for 4 h. The suspension was cooled, poured into water with stirring, and the solid was filtered and dried to give 1.44 g (67%) of the desired nitrile. 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 2.29 (s, 3H), 7.72 (d, J=8.8, 1H), 7.75 (d, J=8.2, 1H), 9.73 (s, 1H); 13C NMR (DMSO-d6) δ 15.3, 23.5, 107.7, 116.5, 123.0, 130.1, 131.5, 135.7, 142.3, 168.8; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.23 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C1 8 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.13 min retention time (95%); MS (ES) m/z 209 [M+H]+.
67%	In N,N-dimethyl-formamide at 150℃; for 4h;	1.C 1C. 3-Chloro-4-cyano-2-methylphenylacetamide; A suspension of bromide 1B (2.7 g, 10.3 mmol) and copper cyanide (0.92 g, 10.3 mmol) in DMF (30 mL) was heated to 150° C. for 4 h. The suspension was cooled, poured into water with stirring, and the solid was filtered and dried to give 1.44 g (67%) of the desired nitrile. 1H NMR (DMSO-d6) δ 2.12 (s, 3H), 2.29 (s, 3H), 7.72 (d, J=8.8, 11H), 7.75 (d, J=8.2, 11H), 9.73 (s, 1H); 13C NMR (DMSO-d6) δ 15.3, 23.5, 107.7, 116.5, 123.0, 130.1, 131.5, 135.7, 142.3, 168.8; HPLC a) column: Phenominex ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.23 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6×50 mm, 4 min gradient, 10% MeOH/90% H2O/0.1% TFA to 90% MeOH/10% H2O/0.1% TFA, 1 min hold, 4 mL/min, UV detection at 220 nm, 2.13 min retention time (95%); MS (ES) m/z 209 [M+H]+.
	In N,N-dimethyl-formamide

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2005/197367, 2005, A1 Location in patent: Page/Page column 18
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/4717, 2007, A1 Location in patent: Page/Page column 17
[3]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]

3
[ 125328-80-5 ]
copper(l) cyanide [ No CAS ]
[ 627531-48-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	In N,N-dimethyl-formamide at 150℃; for 24h;	c c) N-(3-chloro-4-cyano-2-methylphenyl)acetamide c) N-(3-chloro-4-cyano-2-methylphenyl)acetamide A suspension of N-(4-bromo-3-chloro-2-methylphenyl)acetamide (45 g, 0.17 mol) and copper cyanide (34 g, 0.34 mol) in DMF (450 mL) was heated to 150 °C for 24 h. The suspension was cooled, poured into water with stirring. The solid was filtered and dried to give 25 g (70%) of the title compound which was used for the next step without further purification.1H NMR (400 MHz, DMSO-d6): δ 9.73 (bs, 1 H), 7.78 - 7.73 (m, 2H), 2.31 (s, 3H), 2.13 (s, 3H); IR (KBr): 3307, 3097, 3014, 2235, 1930, 1674, 1514 cm"1; MS (ES): m/z 207 (M - 1 ).
70%	In N,N-dimethyl-formamide at 150℃; for 24h;	A1.c c) N-(3-chloro-4-cyano-2-methylphenyl)acetamide A suspension of N-(4-bromo-3-chloro-2-methylphenyl)acetamide (45 g, 0.17 mol) and copper cyanide (34 g, 0.34 mol) in DMF (450 mL) was heated to 150°C. for 24 h. The suspension was cooled, poured into water with stirring. The solid was filtered and dried to give 25 g (70%) of the title compound which was used for the next step without further purification.1H NMR (400 MHz, DMSO-d6): δ 9.73 (bs, 1H), 7.78-7.73 (m, 2H), 2.31 (s, 3H), 2.13 (s, 3H); IR (KBr): 3307, 3097, 3014, 2235, 1930, 1674, 1514 cm-1; MS (ES): m/z 207 (M-1).
67%	In N,N-dimethyl-formamide at 150℃; for 4h;

67%

In DMF (N,N-dimethyl-formamide) at 150℃; for 4h;

4.4C A suspension of bromide 4B (2.70 g, 10.3 mmol) and copper cyanide (0.92 g, 10.3 mmol) in DMF (30 mL) was heated to150 C for 4 h. The suspension was cooled, poured into water with stirring, and the solid was filtered and dried to give 1.44g (67%) of the desirednitrile.'H NMR (DMSO-d6)8 2.12(s, 3H), 2.29 (s, 3H), 7.72 (d,J= 8.8, 1H), 7.75 (d,J= 8.2, 1H), 9.73 (s, 1H); 13C NMR (DMSO-d6)# 15. 3, 23.5, 107.7, 116.5, 123.0, 130.1, 131.5, 135.7, 142.3, 168.8 ; HPLC a) column: Phenominex ODS C18 4.6 x 50 mm, 4 min gradient, 10%MeOH/90%H20/0. 1% TFA to90% MeOH/10%H2O/0. 1% TFA, 1 min hold, 4mL/min, UV detection at 220 nm, 2.23 min retention time; HPLC b) column: Shimadzu Shim-Pack VP-ODS C18 4.6 x 50 mm, 4 min gradient, 10% MeOH/90% H2O/0. 1% TFA to 90% MeOH/10%H20/0-1 % TFA,1 min hold, 4 mL/min, UV detection at 220 nm, 2.13 min retention time (95%); MS (ES)m/z 209 [M+H] +.

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/14627, 2013, A1 Location in patent: Page/Page column 45; 46
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2014/329876, 2014, A1 Location in patent: Paragraph 0429; 0434; 0435
[3]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]
[4]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2005/49580, 2005, A1 Location in patent: Page/Page column 44

4
[ 125328-80-5 ]
[ 573768-09-9 ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3015 - 3025
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864
[3]Patent: WO2013/14627,2013,A1
[4]Patent: US2014/329876,2014,A1

5
[ 125328-80-5 ]
[ 627531-80-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C
	Multi-step reaction with 3 steps 1: Pd(dba)2 / dimethylformamide 2: aq. HCl / ethanol 3: NaHCO₃ / CH₂Cl₂

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]
[2]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]

6
[ 125328-80-5 ]
[ 864361-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: 67 percent / dimethylformamide / 4 h / 150 °C 2.1: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3.1: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4.1: NaH / dioxane / 0.5 h / 20 °C 4.2: 82 percent / CuI / dioxane / 72 h / 100 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

7
[ 125328-80-5 ]
[ 864361-80-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: 67 percent / dimethylformamide / 4 h / 150 °C 2.1: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3.1: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4.1: NaH / dioxane / 0.5 h / 20 °C 4.2: 82 percent / CuI / dioxane / 72 h / 100 °C 5.1: aq. NaOH / methanol / 5 h / 20 °C 5.2: 93 percent / conc. HCl / ethyl acetate / 24 h / 60 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

8
[ 125328-80-5 ]
[ 864661-63-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / K₃PO₄ / CuI; 1,2-cyclohexyldiamine / dioxane / 14 h / 110 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

9
[ 125328-80-5 ]
[ 864661-53-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / K₃PO₄ / CuI; 1,2-cyclohexyldiamine / dioxane / 14 h / 110 °C 5: 88 percent / KOH / tetrahydrofuran; methanol / 3 h / 0 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

10
[ 125328-80-5 ]
[ 945469-30-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

11
[ 125328-80-5 ]
C₂₁H₃₄ClN₃OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

12
[ 125328-80-5 ]
[ 945469-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: 130 mg / i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

13
[ 125328-80-5 ]
[ 757247-59-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: 130 mg / i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: 68 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

14
[ 125328-80-5 ]
[ 757247-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

15
[ 125328-80-5 ]
[ 757247-77-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

16
[ 125328-80-5 ]
[ 757247-78-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

17
[ 125328-80-5 ]
[ 757247-34-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

18
[ 125328-80-5 ]
[ 757248-19-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

19
[ 125328-80-5 ]
[ 757248-20-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

20
[ 125328-80-5 ]
[ 757248-21-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

21
[ 125328-80-5 ]
2-chloro-4-((1R,7S,7aR)-7-hydroxy-1-methyl-3-oxo-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

22
[ 125328-80-5 ]
[ 945469-37-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

23
[ 125328-80-5 ]
C₂₁H₃₄ClN₃OSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

24
[ 125328-80-5 ]
[ 945469-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

25
[ 125328-80-5 ]
[ 757247-60-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

26
[ 125328-80-5 ]
[ 757248-23-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: 130 mg / i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: 68 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: 94 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

27
[ 125328-80-5 ]
2-chloro-4-((1S,7R,7aR)-1-ethyl-7-hydroxy-3-oxo-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: 21 percent / Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: 130 mg / i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: 68 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: 94 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 9: 88 percent / KOH / tetrahydrofuran; methanol / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

28
[ 125328-80-5 ]
C₂₂H₂₀ClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

29
[ 125328-80-5 ]
2-chloro-4-((1S,7R,7aR)-7-hydroxy-1-methyl-3-oxo-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 9: KOH / tetrahydrofuran; methanol / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

30
[ 125328-80-5 ]
C₂₃H₂₂ClN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

31
[ 125328-80-5 ]
2-chloro-4-((1R,7R,7aR)-1-ethyl-7-hydroxy-3-oxo-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C 4: Cs₂CO₃ / Pd₂(dba)3; chiral ferrocenyl catalyst / toluene; dimethylsulfoxide / 48 h / 100 °C 5: TFA / CH₂Cl₂ / 3 h / 20 °C 6: i-Pr₂NEt / tetrahydrofuran; toluene / 1.17 h / 0 - 20 °C 7: Bu₄NF / tetrahydrofuran / 1 h / 20 °C 8: PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 20 °C 9: KOH / tetrahydrofuran; methanol / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

32
[ 125328-80-5 ]
[ 757247-81-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: 93 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

33
[ 125328-80-5 ]
[ 757247-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: 93 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C 5: 69 percent / t-BuOK; p-toluenesulfonyl chloride / tetrahydrofuran / 5.5 h / 20 - 60 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

34
[ 125328-80-5 ]
2-chloro-4-((1S,7R,7aR)-7-hydroxy-3-oxo-1-(trifluoromethyl)-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: 93 percent / i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C 5: 69 percent / t-BuOK; p-toluenesulfonyl chloride / tetrahydrofuran / 5.5 h / 20 - 60 °C 6: 86 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

35
[ 125328-80-5 ]
(2R,3S)-3-(tert-butyldimethylsilanyloxy)-2-[(1S)-(2,2,2-trifluoro-1-hydroxyethyl)]-pyrrolidine-1-carboxylic acid (3-chloro-4-cyano-2-methyl-phenyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

36
[ 125328-80-5 ]
C₂₁H₂₇F₃ClN₃O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C 5: t-BuOK; p-toluenesulfonyl chloride / tetrahydrofuran / 5.5 h / 20 - 60 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

37
[ 125328-80-5 ]
2-chloro-4-((1R,7S,7aR)-7-hydroxy-3-oxo-1-(trifluoromethyl)-tetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-3-methylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C 5: t-BuOK; p-toluenesulfonyl chloride / tetrahydrofuran / 5.5 h / 20 - 60 °C 6: Bu₄NF / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

38
[ 125328-80-5 ]
[ 757248-02-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 85 percent / Na₂CO₃ / CH₂Cl₂; toluene / 130 h / 0 - 20 °C 4: i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]

39
[ 125328-80-5 ]
[ 757247-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 67 percent / dimethylformamide / 4 h / 150 °C 2: 95 percent / conc. HCl; EtOH / 0.5 h / Heating 3: 39 percent / CuI; tert-butylnitrite / acetonitrile / 3 h / 65 °C
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 24 h / 150 °C 2: hydrogenchloride; water / ethanol / Reflux 3: copper(l) iodide; tert.-butylnitrite / acetonitrile / 3 h / Inert atmosphere; Heating
	Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 24 h / 150 °C 2: hydrogenchloride / ethanol / 2 h / Reflux 3: copper(l) iodide; tert.-butylnitrite / acetonitrile / 3 h / 65 °C / Inert atmosphere

Reference： [1]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]
[2]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2014/329876, 2014, A1
[3]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/14627, 2013, A1

40
[ 87-60-5 ]
[ 125328-80-5 ]

Yield	Reaction Conditions	Operation in experiment
96%		22.A 22A. 22A. N-(4-Bromo-3-chloro-2-methylphenyl)acetamide The title compound was prepared (2.75 g, 96% yield) from commercially available 3-chloro-2-methylaniline by procedures analogous to those described in Experiment 2A and 2B.
	Multi-step reaction with 2 steps 1: 100 percent / ethanol / 2 h / 20 °C 2: 96 percent / bromine; glacial acetic acid / 2 h
	Multi-step reaction with 2 steps 1: AcOH; NaOH 2: Br₂

	Multi-step reaction with 2 steps 1: ethanol / 2 h / 20 °C 2: bromine / acetic acid / 24 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: dichloromethane / 20.5 h / 0 - 20 °C 2: bromine; acetic acid / 4 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: ethanol / 20 °C 2: acetic acid; bromine / 24 h / 0 - 20 °C
	Multi-step reaction with 2 steps 1: ethanol / 2 h 2: bromine / acetic acid / 2.5 h / 15 - 20 °C
	Multi-step reaction with 2 steps 1: 12 h / 5 °C 2: acetic acid; bromine / 4 h / -5 - 0 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/19063, 2004, A1 Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2004/181064, 2004, A1
[2]Li, James J.; Sutton, James C.; Nirschl, Alexandra; Zou, Yan; Wang, Haixia; Sun, Chongqing; Pi, Zulan; Johnson, Rebecca; Krystek Jr., Stanley R.; Seethala, Ramakrishna; Golla, Rajasree; Sleph, Paul G.; Beehler, Blake C.; Grover, Gary J.; Fura, Aberra; Vyas, Viral P.; Li, Cindy Y.; Gougoutas, Jack Z.; Galella, Michael A.; Zahler, Robert; Ostrowski, Jacek; Hamann, Lawrence G. [Journal of Medicinal Chemistry, 2007, vol. 50, # 13, p. 3015 - 3025]
[3]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]
[4]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2013/14627, 2013, A1
[5]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[6]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2014/329876, 2014, A1
[7]Current Patent Assignee: MERCK & CO INC - WO2016/8064, 2016, A1
[8]Current Patent Assignee: HUNAN HENGTAI BIOPHARMACEUTICAL - CN110683981, 2020, A

41
[ 125328-80-5 ]
[ 627531-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Pd(dba)2 / dimethylformamide 2: aq. HCl / ethanol 3: NaHCO₃ / CH₂Cl₂ 4: i-Pr₂NEt / toluene

Reference： [1]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]

42
[ 125328-80-5 ]
[ 627530-84-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: Pd(dba)2 / dimethylformamide 2: aq. HCl / ethanol 3: NaHCO₃ / CH₂Cl₂ 4: i-Pr₂NEt / toluene 5: DBU / toluene / 12 h / 20 °C

Reference： [1]Hamann, Lawrence G.; Manfredi, Mark C.; Sun, Chongqing; Krystek Jr., Stanley R.; Huang, Yanting; Bi, Yingzhi; Augeri, David J.; Wang, Tammy; Zou, Yan; Betebenner, David. A.; Fura, Aberra; Seethala, Ramakrishna; Golla, Rajasree; Kuhns, Joyce E.; Lupisella, John A.; Darienzo, Celia J.; Custer, Laura L.; Price, Jennifer L.; Johnson, James M.; Biller, Scott A.; Zahler, Robert; Ostrowski, Jacek [Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 7, p. 1860 - 1864]

43
[ 125328-80-5 ]
[ 544-92-3 ]
[ 573768-09-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	With 1-methyl-pyrrolidin-2-one; copper(l) iodide; at 130℃; for 72h;	Dissolve N-(4-bromo-3-chloro-2-methyl-phenyl)-acetamide (10 g, 38 mmol) in N-methylpyrrolidinone (60 mL) and sparge with nitrogen. Add copper cyanide (10.2 g, 114 mol) and copper iodide (21.8 g, 1 i4 mol) and stir under nitrogen at 130 C for 72 h. Cool the reaction and add ethylene diamine (100 mL), along with water (300 mL). Extract the reaction mixture with EtOAc. Separate and dry the organic portion over Na2SO4, filter, and concentrate. Dissolve the resulting residue in 1 : 1 EtOH/concentrated HCl. Stir at reflux temperature for 30 min, cool and concentrate to half of the volume. Add water (500 mL) and filter. Rinse the filter cake with water and isolate 5.0 g (79%) of the title compound as a white solid. MS: MS (ESI-): 207 (M-I)". MS (ESI+): 209 (M+l)+.

Reference： [1]Patent: WO2006/124447,2006,A2 .Location in patent: Page/Page column 64-65

44
[ 125328-80-5 ]
[ 627531-47-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydrogenchloride; In ethanol; water; at 80℃; for 5h;	100ml flask-N (4-bromo-3 - chloro-2-methylphenyl) Oh theta mid 10g (38.09mmol) and the mixture was stirred into a 38ml ethanol. To the reaction mixture into a 38ml HCl 12N (27eq) it was refluxed at 80 for 5 hours. After the completion of the reaction was concentrated under reduced pressure to give the title compound 8.5g (95%).
	With hydrogenchloride; In ethanol;Reflux;	Step C: 4-bromo-3 -chloro-2-methylaniline To a solution of N-(4-bromo-3-chloro-2-methylphenyl)acetamide (18.50 g, 70.5 mmol) in EtOH(70 mL) was added cone. HC1 (70 mL) at room temperature, and the soluation was heated atreflux overnight. The mixture was adjusted to pH7 with solid Na2CO3, and then extracted byEtOAc, dried and concentrated to afford the title compound. LC/MS [M+1] =220; 222. ?HNIVIR (400 IVIFIz, CDC13) 7.24-7.22 (d, J 8.4 Hz, 1H), 6.48-6.46 (d, J 8.4 Hz, 1H), 2.26 (s,3H).
		A solution of N-(4-bromo-3-chloro-2-methyl-phenyl)-acetamide (3.37 g, 12.80 mmol) in H2SO4: H2O (1:1) was refluxed for 3 hours. The reaction mixture was cooled to room temperature and neutralized with NaOH and extracted with Et2O (3×150 mL). The combined organic phases were washed with H2O (3×100 mL) and brine (1×100 mL), then dried over MgSO4 and concentrated. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded the title aniline. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.31 (s, 3H), 3.93 (br s, 2H), 6.47 (d, J=8.79 Hz, 1H), 7.24 (d, J=7.91 Hz, 1H).

Reference： [1]Patent: KR2015/123007,2015,A .Location in patent: Paragraph 0258-0262
[2]Patent: WO2016/8064,2016,A1 .Location in patent: Page/Page column 56; 57
[3]Patent: US2008/194650,2008,A1 .Location in patent: Page/Page column 24-25

45
[ 627531-47-9 ]
[ 108-24-7 ]
[ 125328-80-5 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 3766 - 3769
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 564 - 574

46
[ 125328-80-5 ]
[ 1447125-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: magnesium sulfate heptahydrate; potassium permanganate / water / 3 h / Reflux 2.1: sodium hydroxide / water / 5 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / Cooling with ice 4.2: 5 h / 20 °C
	Multi-step reaction with 4 steps 1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2.1: sodium hydroxide; water / 4 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 4.2: Inert atmosphere

Reference： [1]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[2]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

47
[ 125328-80-5 ]
[ 1447125-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: magnesium sulfate heptahydrate; potassium permanganate / water / 3 h / Reflux 2.1: sodium hydroxide / water / 5 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / Cooling with ice 4.2: 5 h / 20 °C 5.1: sodium hydride / paraffin oil / 6.5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2.1: sodium hydroxide; water / 4 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 4.2: Inert atmosphere 5.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere

Reference： [1]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[2]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

48
[ 125328-80-5 ]
[ 1447125-28-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: magnesium sulfate heptahydrate; potassium permanganate / water / 3 h / Reflux 2.1: sodium hydroxide / water / 5 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C 4.1: sodium hydride / N,N-dimethyl-formamide; paraffin oil / 0.75 h / Cooling with ice 4.2: 5 h / 20 °C 5.1: sodium hydride / paraffin oil / 6.5 h / 20 °C 6.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2.1: sodium hydroxide; water / 4 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 4.2: Inert atmosphere 5.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 6.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

Reference： [1]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[2]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

49
[ 125328-80-5 ]
[ 125328-77-0 ]

Yield	Reaction Conditions	Operation in experiment
76.1%	With dihydrogen peroxide In water at 50℃; for 4h;	1.3; 23 The third step is to add 200ml of water in a 500ml three-necked flask, and then add 11g of 4-bromo-3-chloro-2-methylphenylacetamide. When the temperature is raised to 50 ° C, add 3g of hydrogen peroxide dropwise within 4 hours , Follow up with TLC, when 4-bromo-3-chloro-2-methylacetanilide is reacted, drop it with sodium bisulfite (20% solution) until no bubbles appear in the reaction system, cool to normal temperature and use again When the pH value of the acidified hydrochloric acid reaches 2.0, a white solid is precipitated, filtered, dried, and recrystallized to obtain 8.5 g of white solid 6-chloro-5-bromo-2-acetamidobenzoic acid. (The yield of this part is 76.1%)
70%	With potassium permanganate; magnesium sulfate heptahydrate In water for 3h; Reflux;
	With potassium permanganate; magnesium sulfate In water for 5.5h; Reflux;

Reference： [1]Current Patent Assignee: HUNAN HENGTAI BIOPHARMACEUTICAL - CN110683981, 2020, A Location in patent: Paragraph 0018; 0020
[2]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[3]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

50
[ 125328-80-5 ]
[ 943138-45-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: magnesium sulfate heptahydrate; potassium permanganate / water / 3 h / Reflux 2: sodium hydroxide / water / 5 h / Reflux 3: pyridine / dichloromethane; acetonitrile / 3 h / 50 °C
	Multi-step reaction with 3 steps 1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2: sodium hydroxide; water / 4 h / Reflux 3: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

Reference： [1]Boettcher, Stephan; Hederos, Markus; Champion, Elise; Dekany, Gyula; Thiem, Joachim [Organic Letters, 2013, vol. 15, # 14, p. 3766 - 3769]
[2]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

51
[ 125328-80-5 ]
[ 7240-90-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: potassium permanganate; magnesium sulfate / water / 5.5 h / Reflux 2.1: sodium hydroxide; water / 4 h / Reflux 3.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere 4.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice 4.2: Inert atmosphere 5.1: sodium hydride / 6.5 h / 20 °C / Inert atmosphere 6.1: potassium <i>tert</i>-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere 7.1: tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate / water; dichloromethane / 20 °C 8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; morpholine / tetrahydrofuran / 20 °C 9.1: potassium carbonate; silver(I) acetate / 0.33 h / 90 - 100 °C 10.1: sodium methylate / methanol / 20 °C

Reference： [1]Boettcher, Stephan; Thiem, Joachim [European Journal of Organic Chemistry, 2014, vol. 2014, # 3, p. 564 - 574]

52
[ 125328-80-5 ]
[ 1044256-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sulfuric acid; water / 3 h / Heating / reflux 1.2: 20 °C 2.1: hydrogenchloride; sodium nitrite / ethanol; water / 2 h / 70 °C 3.1: N-Bromosuccinimide / 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 0.5 h / Heating / reflux

Reference： [1]Current Patent Assignee: ABBVIE INC - US2008/194650, 2008, A1

53
[ 125328-80-5 ]
[ 97329-43-6 ]

Reference： [1]Patent: US2008/194650,2008,A1

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CAS No. :	125328-80-5	MDL No. :	MFCD08059123
Formula :	C₉H₉BrClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	262.53	Pubchem ID :	-
Synonyms :

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 125328-80-5 ]

Quality Control of [ 125328-80-5 ]

Related Doc. of [ 125328-80-5 ]

Product Details of [ 125328-80-5 ]

Safety of [ 125328-80-5 ]

Application In Synthesis of [ 125328-80-5 ]

[ 125328-80-5 ] Synthesis Path-Downstream 1~53

Related Functional Groups of
[ 125328-80-5 ]

Aryls

Bromides

Chlorides

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 125328-80-5 ]

Quality Control of [ 125328-80-5 ]

Related Doc. of [ 125328-80-5 ]

Product Details of [ 125328-80-5 ]

Safety of [ 125328-80-5 ]

Application In Synthesis of [ 125328-80-5 ]

[ 125328-80-5 ] Synthesis Path-Downstream 1~53

Related Functional Groups of [ 125328-80-5 ]

Aryls

Bromides

Chlorides

Amides

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 125328-80-5 ]