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CAS No. : | 3951-89-1 | MDL No. : | MFCD02168781 |
Formula : | C10H10BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 240.10 g/mol | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-dimethylaminopyridine In tetrahydrofuran for 1.5h; Heating; | ||
With luitdine In tetrahydrofuran at 70℃; for 4h; | 2.3 Step 3: Synthesis of compound BB-1B-4 The reactants BB-1B-3 (6 g) and Boc anhydride (15.16 g) were dissolved in tetrahydrofuran (100 mL), and N,N-lutidine (4.58 g) was added to form a mixture. The mixture was stirred at 70°C for 4 hours, quenched with water (100 mL) and was extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with saturated brine (100 mL), dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50:1 to 20:1) to obtain BB-1B-4. MS-ESI (m/z): 283.9[M-55]+ | |
With luitdine In tetrahydrofuran at 70℃; for 4h; | 2.3 Step 3: Synthesis of compound BB-1B-4 The reactants BB-1B-3 (6 g) and Boc anhydride (15.16 g) were dissolved in tetrahydrofuran (100 mL), and N,N-lutidine (4.58 g) was added to form a mixture. The mixture was stirred at 70°C for 4 hours, quenched with water (100 mL) and was extracted with ethyl acetate (100 mL×3). The combined organic layer was washed with saturated brine (100 mL), dried with anhydrous sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 50:1 to 20:1) to obtain BB-1B-4. MS-ESI (m/z): 283.9[M-55]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21% | With sulfuric acid; acetic acid at 90℃; for 2.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 8: 91 percent / HCl / ethyl acetate / 20 °C 9: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 87 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 8: 91 percent / HCl / ethyl acetate / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating | ||
Multi-step reaction with 4 steps 1.1: luitdine / tetrahydrofuran / 4 h / 70 °C 2.1: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3.1: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C 4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C | ||
Multi-step reaction with 3 steps 1: luitdine / tetrahydrofuran / 4 h / 70 °C 2: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating | ||
Multi-step reaction with 2 steps 1: luitdine / tetrahydrofuran / 4 h / 70 °C 2: sodium methoxide / 2 h / 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating | ||
Multi-step reaction with 6 steps 1.1: luitdine / tetrahydrofuran / 4 h / 70 °C 2.1: sodium methoxide / 2 h / 100 °C / Inert atmosphere 3.1: sodium tetrahydridoborate; methanol / tetrahydrofuran / 0.5 h / -40 - -15 °C 4.1: triethylamine; methanesulfonyl chloride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II) dichloromethane adduct / lithium hydroxide monohydrate; dimethyl sulfoxide / 16 h / 80 °C / Inert atmosphere 6.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C 9: 98 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 7: 93 percent / aq. HCl / ethyl acetate / 80 °C 8: 97 percent / pyridine / tetrahydrofuran / 0.5 h / 20 °C 9: 98 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 9: 84 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 76 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 12 h / 20 °C 8: 62 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 9: 84 percent / aq. NaOH / tetrahydrofuran; methanol / 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 96 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH2Cl2 / 20 °C 9: 75 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 82 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH2Cl2 / 20 °C 9: 75 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 71 percent / copper(II) pivalate / CH2Cl2 / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 96 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 100 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 78 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1: DMAP / tetrahydrofuran / 1.5 h / Heating 2: 3.89 g / sodium methoxide / 2.5 h / Heating 3: NaBH4 / tetrahydrofuran; methanol / 1 h / -15 °C 4: Et3N / tetrahydrofuran / 14 h / 20 °C 5: 2.53 g / 1,8-diazabicyclo[5,4,0]undec-7-ene / tetrahydrofuran / 0.17 h / Heating 6: 100 percent / aq. HCl / ethyl acetate / 0.5 h / 80 °C 7: 56 percent / aq. K2CO3; Pd(PPh3)4 / toluene; ethanol / Heating 8: 88 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 78 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C |
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