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[ CAS No. 886615-30-1 ]

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Chemical Structure| 886615-30-1
Chemical Structure| 886615-30-1
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Product Details of [ 886615-30-1 ]

CAS No. :886615-30-1 MDL No. :MFCD11111905
Formula : C7H3BrClFO Boiling Point : 253°C
Linear Structure Formula :- InChI Key :N/A
M.W :237.45 g/mol Pubchem ID :-
Synonyms :

Safety of [ 886615-30-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H319-H315-H302-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 886615-30-1 ]

  • Downstream synthetic route of [ 886615-30-1 ]

[ 886615-30-1 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 33513-42-7 ]
  • [ 886615-30-1 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.166667h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - 20℃; 7 Preparation 7; 3-bromo-6-chloro-2-fluoro-benzaldehyde; Add a 2M LDA in THF (22 mL, 44 mmol) to l-bromo-4-chloro-2-fluorobenzene(9.2 g, 44 mmol) in THF (100 mL) at -780C. Stir for 10 minutes. Add DMF (1OmL, 132 mmol) and warm up to room temperature. Add the reaction mixture to ice and water. Extract the mixture with ethyl acetate (100 mL). Wash the organic layer with aqueous LiCl (20 mL, 10%), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to obtain 5 g (48 %) of the title compound as a white solid.
  • 2
  • [ 886615-30-1 ]
  • [ 886615-31-2 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: 3-bromo- 6-chloro-2-fluorobenzaldehyde With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 20℃; Stage #2: With hydrogenchloride; water In tetrahydrofuran 8 Preparation 8; (3-bromo-6-chloro-2-fluoro-phenyl)methanol; Add IM LAH in THF (20 mL, 20 mmol) to 3-bromo-6-chloro-2-fluoro- benzaldehyde (Preparation 7) (4.9 g, 20 mmol) in THF (20 mL) at -780C. Stir for 15 minutes and warm up to room temperature. Add reaction mixture into ice and water. Add IM HCl (5 mL, 5 mmol) to dissolve the solid. Extract the mixture with ethyl acetate (50 mL), dry with magnesium sulfate, filter and evaporate solvent under reduced pressure to obtain 4.6 g (94 %) of the title compound as a white solid.
Stage #1: 3-bromo- 6-chloro-2-fluorobenzaldehyde With sodium tetrahydroborate In ethanol at 20℃; for 1h; Stage #2: With water In ethanol 15 15. Preparation of (3-bromo-6-chloro-2-fluorophenyl) methanol; To a solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (20.0 g, 0.084 mol) in ethanol (250 mL) was added sodium borohydride (6.4 g, 0.168 mol) and the reaction mixture was stirred at ambient temperature for 1 hour. The mixture was diluted with water (300 mL) and extracted with ethyl acetate (2×200 mL), dried (sodium sulfate) and concentrated. The crude solid was recrystallized from hexanes to give (3-bromo-6-chloro-2-fluorophenyl) methanol (10.4 g, 0.043 mol): 1H NMR (CDCl3): δ 7.50 (m, 1H), 7.15 (dt, 1H), 4.90 (s, 2H), 2.10 (bs, 1H).
  • 3
  • [ 886615-30-1 ]
  • 1-bromo-4-chloro-2-fluoro-3-difluoromethylbenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 1h; 9 9. Preparation of l-bromo-4-chloro-2-fluoro-3-difluoromethylbenzene; Diethylamino sulfur trifluoride (15.3 g, 0.096 mol) was added slowly to a solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (7.50 g, 0.032 mol) in methylene chloride at 0° C. The resulting solution was stirred for one hour and then allowed to warm to room temperature. The reaction was carefully quenched with a saturated solution of sodium bicarbonate in water (100 mL) and extracted with methylene chloride (2 x 75 mL). The combined organic extracts were dried and concentrated to give l-bromo-4-chloro-2-fluoro-3-difluoro- methylbenzene (7.20 g, 0.028 mol): 1H NMR (CDCl3): δ 7.60 (m, IH), 7.05 (m, IH), 7.00 (d, IH).
With diethylamino-sulfur trifluoride In dichloromethane at 0 - 20℃; for 1h; 9 9. Preparation of 1-bromo-4-chloro-2-fluoro-3-difluoromethylbenzene; Diethylamino sulfur trifluoride (15.3 g, 0.096 mol) was added slowly to a solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (7.50 g, 0.032 mol) in methylene chloride at 0° C. and the mixture stirred for 1 hour after allowing to warm to ambient temperature. The reaction was carefully quenched with a saturated solution of sodium bicarbonate in water (100 mL) and extracted with methylene chloride (2×75 mL) and the combined extracts dried (sodium sulfate) and concentrated to give 1-bromo-4-chloro-2-fluoro-3-difluoromethylbenzene (7.20 g, 0.028 mol): 1H NMR (CDCl3): δ 7.60 (m, 1H), 7.05 (m, 1H), 7.00 (d, 1H).
  • 4
  • [ 886615-30-1 ]
  • 3-bromo-6-chloro-2- fluorobenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
91% With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; 15 15. Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile; A suspension of 3-bromo-6-chloro-2-fluorobenzaldehyde (9.0 g, 0.04 mol) and hydroxylamine-0-sulfonic acid (7.50 g, 0.07 mole) in water (300 mL) was heated at 50° C for eighteen hours. The suspension was cooled and the solid was collected to give 3-bromo-6-chloro-2-fluorobenzonitrile (8.8 g, 0.04 mol): 1H NMR (CDCl3): δ 7.75 (m, IH), 7.25 (m, IH).
With hydroxylamido-O-sulfinic acid In water at 50℃; for 18h; 22 22. Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile; A suspension of 3-bromo-6-chloro-2-fluorobenzaldehyde (9.0 g, 0.04 mol) and O-sulfinic acid hyrdroxyamine (7.50 g, 0.07 mole) in water (300 mL) was warmed to 50° C. for 18 hours. The suspension was cooled and the solid collected to give 3-bromo-6-chloro-2-fluorobenzonitrile (8.8 g, 0.04 mol): 1H NMR (CDCl3): δ 7.75 (m, 1H), 7.25 (m, 1H).
With hydroxylamine-O-sulfonic acid In water at 20 - 50℃; for 18h; 2 Step-2: Synthesis of 3-bromo-6-chloro-2-fluorobenzonitrile A3 (0605) 1.0 equiv.) in water (2.1 L) was charged with Hydroxylamine-6>-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.) at room temperature. The reaction mixture was heated to 50 °C and stirred for 18 h. After reaction completion (the reaction progress was monitored by TLC), it was cooled to room temperature and stirred for 1-1.5 h. The solids were filtered and washed with water. The wet solid was dried at 50 °C under vacuum for 12-15 h to afford the crude 3-Bromo-6-chloro-2-fluorobenzonitrile A3 as a solid; which can be directly used for the next reaction without further purification. Yield: 190.0 g, 91 % (reported 92%). NMR (400 MHz, CDC ): δ 7.50 (dd, Ji = 7.1 Hz, J2 = 8.6 Hz, 1H), 7.15 (dd, Ji = 1.4 Hz, J2 = 8.7 Hz, 1H).
With hydroxylamine hydrochloride; acetic anhydride; acetic acid at 45 - 75℃; Large scale; I.7 6a (98.5 kg) was charged to a reactor containing acetic anhydride (105 kg) and acetic acid (621 kg) at 20 °C. The mixture was heated to about 45 °C and hydroxyl amine (1619) hydrochloride (31.5 kg) was charged. The reaction was heated to about 75 °C and agitated until the reaction was complete. The product was isolated from the reaction mixture by adding water (788 kg) at about 45 °C. The mixture was cooled to about 25 °C and then the slurry was filtered. The filtered cake was washed with water (197 kg,). The cake was dried to afford 6b. 1H NMR (400 MHz, DMSO- ) 5 8.11 (dd, , 7= 8.8, 1.4 Hz, 1H), 7.58 (dd, ./= 8.8, 1.4 Hz, 1H).
190.0 g With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; Step-2: Synthesis of 3 -bromo-6-chloro-2-fluorobenzonitrile To a solution of 3-Bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) was charged with Hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.) at room temperature. The reaction mixture was heated to 50 °C and stirred for 18 h. After reaction completion (the reaction progress was monitored by TLC), it was cooled to room temperature and stirred for 1-1.5 h. The solids were filtered and washed with water. The wet solid was dried at 50 °C under vacuum for 12-15 h to afford the crude 3-Bromo-6-chloro-2-fluorobenzonitrile as a solid; which can be directly used for the next reaction without further purification. Yield: 190.0 g, 91% (reported 92%). NMR (400 MHz, CDCb): d 7.50 (dd, Ji = 7.1Hz, J2 = 8.6 Hz, 1H), 7.15 (dd, Ji = A Hz, J2 = 8.7 Hz, 1H).
190 g With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; 3-bromo-6-chloro-2-fiuorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
190 g With hydroxylamine-O-sulfonic acid In water at 20 - 50℃; for 19.5h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
190 g With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
190.0 g With hydroxylamine-O-sulfonic acid In water at 20 - 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
190.0 g With hydroxylamine-O-sulfonic acid In water at 20 - 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).
190 g With hydroxylamine-O-sulfonic acid In water at 50℃; for 18h; Preparation of 3-bromo-6-chloro-2-fluorobenzonitrile To a stirred solution of 3-bromo-6-chloro-2-fluorobenzaldehyde (210.0 g, 0.89 mol, 1.0 equiv.) in water (2.1 L) at room temperature was added hydroxylamine-O-sulfonic acid (175.15 g, 1.55 mol, 1.75 equiv.). The reaction mixture was heated to 50 °C and stirred for 18 h). The mixture was cooled to room temperature and stirred for 1-1.5 h. The solids were isolated via filtration and were then washed with water. The wet solid was dried under vacuum at 50 °C for 12-15 h to afford 3-bromo-6-chloro-2-fluorobenzaldehyde, 190.0 g (91%).

  • 5
  • [ 1996-29-8 ]
  • [ 33513-42-7 ]
  • [ 886615-30-1 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.25h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 20℃; xvi.a (a) 3-Bromo-6-chloro-2-fluorobenzaldehyde (130) To a solution of 1-bromo-4-chloro-2-fluorobenzene (10.0 g, 47.8 mmol) in dry THF (300 ml.) at -78 °C under nitrogen was added LDA (2.0 M solution in THF, 31 ml_, 62.1 mmol) dropwise and the mixture was stirred at -78 °C for 15 min. DMF (7.00 g, 95.8 mmol) was added and the mixture was allowed to warm to room temperature. The reaction mixture was quenched with a saturated aqueous NH4CI solution and the mixture was extracted with EtOAc (400 ml. x 3). The combined organic extracts were washed with brine (300 ml_), dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (100% Pet. Ether) to give the title compound (4.0 g, 35%) as a white solid, which was used directly in the next step.
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50℃; 8 8. Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde; A solution of l-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at -500C. The resulting solution was then warmed to -20° C and cooled again to -50° C. A solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture was allowed to warm to room temperature. The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2 x 150 mL). The combined organic phases were dried and concentrated. The product was recrystallized from hexane to give 3-bromo-6-chloro-2-fluorobenzaldehyde (40.0 g, 0.169 mol): mp 92-930 C.
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 20℃; 7 7. Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde; A solution of 1-bromo-4-chloro-2-fluorobenzene (20.4 g, 0.100 mol) in THF (50 mL) was slowly added to LDA (0.125 mol) in THF (600 mL) at -50° C. After addition the solution was warmed to -20° C. and then cooled to -50° C. and a solution of DMF (14.6 g, 0.20 mol) in THF (50 mL) was slowly added and the reaction mixture was warmed to ambient temperature. The reaction was quenched with water (250 mL) and extracted with ethyl acetate (2×150 mL) and the combined organic phases were dried (sodium sulfate) and concentrated. The solid residue was recrystallized from hexane to give 3-bromo-6-chloro-2-fluorobenzaldehyde (40.0 g, 0.169 mol): mp 92-93° C.
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; 1 Step-1 : Synthesis of 3-bromo-6-chloro-2-fluorobenzaldehyde 2 To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene Al (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added 2.0 M lithium diisopropylamide (LDA) in THF (620 mL, 1.24 mol, 1.3 equiv.) at -50 °C, the reaction mixture was allowed to -20 °C and stirred for 1 h. Then it was re-cooled to -50 °C and slowly added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) at the same temperature. The mixture was allowed to 0 °C and stirred for 30-45 min. After completion of the reaction (monitored by TLC), it was quenched with the slow addition of ice cold water (2.0 L); then diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1 0 L); 1.0 N HC1 (1 0 L) and 1 % NaCl solution (2.0 L). The organic layer was dried over anhydrous Na2SC , concentrated under vacuum. The resultant crude solid was directly used for next step without further purification. Yield: 210.0 g, 93% (reported 78%). NMR (400 MHz, CDCb): δ 10.39 (d, J= 0.8 Hz, 1H), 7.69 (dd, Ji = 7.2 Hz, J2 = 8.8 Hz, 1H), 7.19 (dd, Ji = 1.2 Hz, J2 = 8.4 Hz, 1H).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -35 - -30℃; Large scale; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -35 - -30℃; Large scale; I.7 To a reactor was added tetrahydrofuran (THF, 275 kg) and diisopropyl amine (DIP A, 30 kg) and the mixture was cooled to about -35 °C. nButyl lithium (2.5 mol/L in hexanes, 74 kg) was charged slowly keeping the reaction temperature less than -30 °C. The mixture was agitated at-35 °C until the reaction was complete. 1 -brom o-4-chl oro-2-fluorobenzene (52 kg) was charged keeping reaction temperature less than 30 °C and the mixture was agitated at -35°C until reaction was complete. N,N-dimethylform amide (DMF, 36 kg) was charged keeping reaction temperature less than -30 °C and the mixture was agitated at about -35 °C until reaction was complete. Hydrochloric acid (HO, 18 mass% in water, 147 kg) was charged keeping reaction temperature less than -5 °C. The reaction was warmed to about 0 °C, water (312 kg) was added, and the reaction was extracted with methyl tert-butyl ether (MTBE, 770 kg). The organic was warmed to about 20 °C and washed with brine (NaCl, 23.5 mass% in water, 1404 kg). The mixture was distilled to about 3-4 volumes and heptane was charged (354 kg). The product was isolated by distillation to 3-4 volumes. The slurry was filtered and washed with heptane (141 kg) and dried to afford 6a. 1H NMR (400 MHz, DMSO-i/6) d 10.23 (d, J= 1.2 Hz, 1H), 8.00 (dd, j = 8.7, 1.4 Hz, 1H), 7.44 (dd, j= 8.7, 1.4 Hz, 1H).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; 1 Step-l: Synthesis of 3-bromo-6-chloro-2-fluorobenzaldehyde 2Reaction scheme: To a stirred solution of l-Bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added 2.0 M lithium diisopropylamide (LDA) in THF (620 mL, 1.24 mol, 1.3 equiv.) at -50 °C, the reaction mixture was allowed to -20 °C and stirred for 1 h. Then it was re-cooled to -50 °C and slowly added DMF (184.8 mL,2.48 mol, 2.6 equiv.) at the same temperature. The mixture was allowed to 0 °C and stirred for 30-45 min. After completion of the reaction (monitored by TLC), it was quenched with the slow addition of ice cold water (2.0 L); then diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and.5% NaCl solution (2.0 L). The organic layer was dried over anhydrous NaiSOr. concentrated under vacuum. The resultant crude solid was directly used for next step without further purification. Yield: 210.0 g, 93% (reported 78%). NMR (400 MHz, CDCb): d 10.39 (d, J= 0.8 Hz, 1H), 7.69 (dd, Ji = 7.2 Hz, J2 = 8.8 Hz, 1H), 7.19 (dd, Ji = 1.2 Hz, J2 = 8.4 Hz, 1H).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; 3-bromo-6-chloro-2-Jluorobenzaldehyde To a stirred solution of l-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 F) was added a solution of FDA in THF (2.0 M, 620 mF, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mF, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C) The mixture was quenched via the slow addition of ice cold water (2.0 F). The reaction mixture was diluted with ethyl acetate (2.0 F) and stirred for 15 min at room temperature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 F). The combined organic layers were washed with water (2 x 1.0 F); 1.0 N HC1 (1.0 F) and then 15% NaCl solution (2.0 F). The organic solution was dried over NaiSCri: filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde To a stirred solution of 1-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added a solution of LDA in THF (2.0 M, 620 mL, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C). The mixture was quenched via the slow addition of ice-cold water (2.0 L). The reaction mixture was diluted with ethyl acetate (2.0 L) and stirred for 15 min at room tempreature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HCl (1.0 L) and then 15% NaCl solution (2.0 L). The organic solution was dried over Na2SO4; filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde To a stirred solution of l-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added a solution of LDA in THF (2.0 M, 620 mL, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C). The mixture was quenched via the slow addition of ice cold water (2.0 L). The reaction mixture was diluted with ethyl acetate (2.0 L) and stirred for 15 min at room tempreature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and then l5% NaCl solution (2.0 L). The organic solution was dried over NaiSOr: filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde To a stirred solution of l-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 F) was added a solution of FDA in THF (2.0 M, 620 mF, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C). The mixture was quenched via the slow addition of ice cold water (2.0 L). The reaction mixture was diluted with ethyl acetate (2.0 L) and stirred for 15 min at room tempreature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and then 15% NaCl solution (2.0 L). The organic solution was dried over NaiSOr: filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde To a stirred solution of l-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 F) was added a solution of FDA in THF (2.0 M, 620 mF, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C). The mixture was quenched via the slow addition of ice cold water (2.0 L). The reaction mixture was diluted with ethyl acetate (2.0 L) and stirred for 15 min at room tempreature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HC1 (1.0 L) and then 15% NaCl solution (2.0 L). The organic solution was dried over NaiSOr: filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).
Stage #1: 1-bromo-4-chloro-2-fluorobenzene With lithium diisopropyl amide In tetrahydrofuran at -50 - -20℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -50 - 0℃; Preparation of 3-bromo-6-chloro-2-fluorobenzaldehyde To a stirred solution of l-bromo-4-chloro-2-fluorobenzene (200 g, 0.955 mol, 1.0 equiv.) in anhydrous THF (2.0 L) was added a solution of LDA in THF (2.0 M, 620 mL, 1.24 mol, 1.3 equiv.) at -50 °C. The reaction mixture was allowed to warm to -20 °C and was stirred for 1 h. The mixture was cooled to -50 °C and slowly to the mixture was added DMF (184.8 mL, 2.48 mol, 2.6 equiv.) maintaining a temperature of -50 °C. The mixture was allowed to warm to 0 °C and was stirred for 30-45 min at the same temperature (0 °C). The mixture was quenched via the slow addition of ice cold water (2.0 L). The reaction mixture was diluted with ethyl acetate (2.0 L) and stirred for 15 min at room temperature. The organic layer was separated and reserved; the aqueous layer was extracted with ethyl acetate (2 x 1.0 L). The combined organic layers were washed with water (2 x 1.0 L); 1.0 N HCI (1.0 L) and then 15% NaCI solution (2.0 L). The organic solution was dried over Na2SC>4; filtered; and then concentrated in vacuo. The resultant crude solid was used directly in the next step without further purification. Yield for the crude product: 210.0 g (93%).

  • 6
  • [ 886615-30-1 ]
  • C16H11Br2ClFN5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 23 °C 2: N,N-dimethyl-formamide / 3 h / 155 °C 3: sodium tetrahydroborate / methanol / 4 h
  • 7
  • [ 886615-30-1 ]
  • C16H9Br2ClFN5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 16 h / 23 °C 2: N,N-dimethyl-formamide / 3 h / 155 °C
  • 8
  • [ 886615-30-1 ]
  • [ 2142-63-4 ]
  • C15H8Br2ClFO [ No CAS ]
YieldReaction ConditionsOperation in experiment
38% With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 23℃; for 16h;
  • 9
  • [ 886615-30-1 ]
  • 7-bromo-4-chloro-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C
Multi-step reaction with 2 steps 1: hydroxylamine hydrochloride; acetic anhydride; acetic acid / 45 - 75 °C / Large scale 2: hydrazine hydrate / water; isopropyl alcohol / 80 °C / Large scale
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine hydrate / ethanol / 1 h / 80 °C
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 19.5 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 80 °C
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine hydrate / ethanol / 1 h / 80 °C
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine hydrate / ethanol / 1 h / 80 °C

  • 10
  • [ 886615-30-1 ]
  • 7-bromo-4-chloro-1-(2,2-difluoroethyl)-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice
Multi-step reaction with 3 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 19.5 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C
Multi-step reaction with 3 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C

  • 11
  • [ 886615-30-1 ]
  • N-(7-bromo-4-chloro-1-(2,2-difluoroethyl)-1H-indazol-3-yl)methane sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 4 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 4.2: 2 h / 20 °C
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 19.5 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C
Multi-step reaction with 4 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 4.3: 2 h / 20 °C

  • 12
  • [ 886615-30-1 ]
  • N- (7-bromo-4-chloro-1-(2,2-difluoroethyl)-1H-indazol-3-yl)-N-(4-methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 5 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 4.2: 2 h / 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 19.5 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C
Multi-step reaction with 5 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 4.3: 2 h / 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C

  • 13
  • [ 886615-30-1 ]
  • N-(4-chloro-1-(2,2-difluoroethyl)-7-((diphenylmethylene)amino)-1H-indazol-3-yl)-N-(4-methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 95 °C / Inert atmosphere
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; palladium diacetate; caesium carbonate / 1,4-dioxane / 2 h / 95 °C
  • 14
  • [ 886615-30-1 ]
  • N'-(7-amino-4-chloro-1-(2,2-difluoroethyl)-1H-indazol-3-yl)-N'-(4-methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 95 °C / Inert atmosphere 7.1: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: copper(l) iodide; sodium L-ascorbate; sodium azide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / water; 1-methyl-pyrrolidin-2-one / 15 h / 100 °C
Multi-step reaction with 7 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C / Cooling with ice 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; palladium diacetate; caesium carbonate / 1,4-dioxane / 2 h / 95 °C 7.1: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C
Multi-step reaction with 6 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6: copper(l) iodide; sodium L-ascorbate; sodium azide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / water; 1-methyl-pyrrolidin-2-one / 15 h / 20 - 100 °C
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 20 - 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 4.2: 2 h / 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: copper(l) iodide; sodium L-ascorbate; sodium azide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane / water; 1-methyl-pyrrolidin-2-one / 15 h / 20 - 100 °C
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: copper(l) iodide; sodium L-ascorbate; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium azide / water; 1-methyl-pyrrolidin-2-one / 15 h / 100 °C
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 19.5 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: copper(l) iodide; sodium L-ascorbate; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium azide / water; 1-methyl-pyrrolidin-2-one / 15 h / 100 °C
Multi-step reaction with 6 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2.1: hydrazine hydrate / ethanol / 1 h / 80 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0.08 h 4.2: 2 h / 0 - 20 °C 4.3: 2 h / 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C 6.1: copper(l) iodide; sodium L-ascorbate; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; sodium azide / water; 1-methyl-pyrrolidin-2-one / 15 h / 100 °C

  • 15
  • [ 886615-30-1 ]
  • tert-butyl (S)-(1-(3-(4-chloro-1-(2,2-difluoroethyl)-3-(N-(4-methoxybenzyl)methylsulfonamido)-1H-indazol-7-yl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)-2-(3,5-difluorophenyl)ethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 95 °C / Inert atmosphere 7.1: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C 8.1: diphenyl hydrogen phosphite / pyridine / 2 h / 70 °C
  • 16
  • [ 886615-30-1 ]
  • N-(7-(2-(1-amino-2-(3,5-difluorophenyl)ethyl)-4-oxopyrido[2,3-d]pyrimidin-3(4H)-yl)-4-chloro-1-(2,2-difluoroethyl)-1H-indazol-3-yl)-N-(4-methoxybenzyl)methanesulfonamide hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 95 °C / Inert atmosphere 7.1: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C 8.1: diphenyl hydrogen phosphite / pyridine / 2 h / 70 °C 9.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C
  • 17
  • [ 886615-30-1 ]
  • N-((S)-1-(3-(4-chloro-1-(2,2-difluoroethyl)-3-(N-(4-methoxybenzyl)methylsulfonamido)-1H-indazol-7-yl)-4-oxo-3,4-dihydropyrido[2,3-d]pyrimidin-2-yl)-2-(3,5-difluorophenyl)ethyl)-2-((3bS,4aR)-3-(difluoromethyl)-5,5-difluoro-3b,4,4a,5-tetrahydro-1H-cyclopropa[3,4]cyclopenta[1,2-c]pyrazol-1-yl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 10 steps 1.1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2.1: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3.1: potassium <i>tert</i>-butylate / tetrahydrofuran / 0.17 h / 0 °C 3.2: 2 h / 0 - 20 °C 4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C 5.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C 6.1: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 95 °C / Inert atmosphere 7.1: water; hydrogenchloride / tetrahydrofuran / 2 h / 20 °C 8.1: diphenyl hydrogen phosphite / pyridine / 2 h / 70 °C 9.1: hydrogenchloride / 1,4-dioxane / 0.5 h / 20 °C 10.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 2 h
  • 18
  • [ 886615-30-1 ]
  • 2-(7-bromo-4-chloro-1H-indazol-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation
Multi-step reaction with 3 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation
  • 19
  • [ 886615-30-1 ]
  • 2-(7-bromo-4-chloro-1-cyclopropyl-1H-indazol-3-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere
Multi-step reaction with 4 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere
  • 20
  • [ 886615-30-1 ]
  • 7-bromo-4-chloro-1-cyclopropyl-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C
Multi-step reaction with 5 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C
  • 21
  • [ 886615-30-1 ]
  • N-(7-bromo-4-chloro-1-cyclopropyl-1H-indazol-3-yl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice
Multi-step reaction with 6 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice
  • 22
  • [ 886615-30-1 ]
  • N-(7-bromo-4-chloro-1-cyclopropyl-1H-indazol-3-yl)-N-(4- methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 7 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C
  • 23
  • [ 886615-30-1 ]
  • N-(4-chloro-1-cyclopropyl-7-((diphenylmethylene)amino)-1H-indazol-3-yl)-N-(4-methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C 8: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 120 °C / Microwave irradiation
Multi-step reaction with 8 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C 8: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 2 h / 120 °C / Microwave irradiation
  • 24
  • [ 886615-30-1 ]
  • N-(7-amino-4-chloro-1-cyclopropyl-1H-indazol-3-yl)-N-(4- methoxybenzyl)methanesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 9 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: hydrazine hydrate / ethanol / 15 h / 20 - 110 °C 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: sodium carbonate; copper diacetate; [2,2]bipyridinyl / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C 8: caesium carbonate; palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl / 1,4-dioxane / 2 h / 120 °C / Microwave irradiation 9: hydrogenchloride / water; tetrahydrofuran / 2 h / 20 °C
Multi-step reaction with 9 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: hydrazine / ethanol / 0.58 h / 120 °C / Microwave irradiation 3: 1,4-dioxane / 2 h / 150 °C / Microwave irradiation 4: [2,2]bipyridinyl; copper diacetate; sodium carbonate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere 5: hydrazine hydrate / tetrahydrofuran; ethanol / 3 h / 20 °C 6: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / Cooling with ice 7: caesium carbonate / N,N-dimethyl-formamide / 20 °C 8: (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; caesium carbonate / 1,4-dioxane / 2 h / 120 °C / Microwave irradiation 9: hydrogenchloride; water / tetrahydrofuran / 2 h / 20 °C
  • 25
  • [ 886615-30-1 ]
  • 7-bromo-4-chloro-1-isopropyl-1H-indazol-3-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 20 - 50 °C 2: sodium methylate / ethanol / 0.58 h / 120 °C / Microwave irradiation
Multi-step reaction with 2 steps 1: hydroxylamine-O-sulfonic acid / water / 18 h / 50 °C 2: sodium methylate / ethanol / 0.58 h / 120 °C / Microwave irradiation
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