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[ CAS No. 3951-89-1 ]

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Chemical Structure| 3951-89-1
Chemical Structure| 3951-89-1
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Product Details of [ 3951-89-1 ]

CAS No. :3951-89-1 MDL No. :MFCD02168781
Formula : C10H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :XIFKOJPBXZKSAZ-UHFFFAOYSA-N
M.W :240.10 Pubchem ID :22329108
Synonyms :

Safety of [ 3951-89-1 ]

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:

Application In Synthesis of [ 3951-89-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3951-89-1 ]

[ 3951-89-1 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 3951-89-1 ]
  • [ 24424-99-5 ]
  • [ 313724-26-4 ]
YieldReaction ConditionsOperation 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]+
  • 2
  • 7-bromo-5-oxo-2,3,4,5-tetrahydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carboxylic acid ethyl ester [ No CAS ]
  • [ 3951-89-1 ]
YieldReaction ConditionsOperation in experiment
21% With sulfuric acid; acetic acid at 90℃; for 2.5h;
  • 3
  • [ 3951-89-1 ]
  • [ 313724-44-6 ]
YieldReaction ConditionsOperation 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
  • 4
  • [ 3951-89-1 ]
  • [ 313736-13-9 ]
YieldReaction ConditionsOperation 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
  • 5
  • [ 3951-89-1 ]
  • [ 313736-39-9 ]
YieldReaction ConditionsOperation 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
  • 6
  • [ 3951-89-1 ]
  • 7-bromo-1-(3-methyl-butyl)-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 7
  • [ 3951-89-1 ]
  • [ 313736-45-7 ]
YieldReaction ConditionsOperation 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
  • 8
  • [ 3951-89-1 ]
  • [ 313724-37-7 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 3951-89-1 ]
  • 7-Bromo-5-hydroxy-2,3,4,5-tetrahydro-benzo[b]azepine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 3951-89-1 ]
  • [ 313724-31-1 ]
YieldReaction ConditionsOperation 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
  • 11
  • [ 3951-89-1 ]
  • 7-bromo-5-methanesulfonyloxy-2,3,4,5-tetrahydro-benzo[<i>b</i>]azepine-1,4-dicarboxylic acid 1-<i>tert</i>-butyl ester 4-methyl ester [ No CAS ]
YieldReaction ConditionsOperation 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
  • 12
  • [ 3951-89-1 ]
  • [ 313724-71-9 ]
YieldReaction ConditionsOperation 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
  • 13
  • [ 3951-89-1 ]
  • [ 313750-60-6 ]
YieldReaction ConditionsOperation 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
  • 14
  • [ 3951-89-1 ]
  • [ 313727-06-9 ]
YieldReaction ConditionsOperation 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
  • 15
  • [ 3951-89-1 ]
  • 1-acetyl-7-(4-morpholin-4-yl-phenyl)-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 3951-89-1 ]
  • [ 313727-12-7 ]
YieldReaction ConditionsOperation 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
  • 17
  • [ 3951-89-1 ]
  • [ 597583-16-9 ]
YieldReaction ConditionsOperation 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
  • 18
  • [ 3951-89-1 ]
  • [ 313736-28-6 ]
YieldReaction ConditionsOperation 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
  • 19
  • [ 3951-89-1 ]
  • [ 313736-34-4 ]
YieldReaction ConditionsOperation 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
  • 20
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-cyclopropylmethyl-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 21
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-phenyl-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 22
  • [ 3951-89-1 ]
  • [ 313729-65-6 ]
YieldReaction ConditionsOperation 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
  • 23
  • [ 3951-89-1 ]
  • [ 313724-66-2 ]
YieldReaction ConditionsOperation 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
  • 24
  • [ 3951-89-1 ]
  • [ 313730-21-1 ]
YieldReaction ConditionsOperation 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
  • 25
  • [ 3951-89-1 ]
  • [ 313730-15-3 ]
YieldReaction ConditionsOperation 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
  • 26
  • [ 3951-89-1 ]
  • [ 313729-70-3 ]
YieldReaction ConditionsOperation 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
  • 27
  • [ 3951-89-1 ]
  • [ 719297-14-0 ]
YieldReaction ConditionsOperation 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
  • 28
  • [ 3951-89-1 ]
  • [ 313729-45-2 ]
YieldReaction ConditionsOperation 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
  • 29
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-thiazol-2-ylmethyl-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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
  • 30
  • [ 3951-89-1 ]
  • [ 313751-90-5 ]
YieldReaction ConditionsOperation 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
  • 31
  • [ 3951-89-1 ]
  • [ 313729-50-9 ]
YieldReaction ConditionsOperation 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: 89 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C
  • 32
  • [ 3951-89-1 ]
  • 1-benzyl-7-[4-(2-butoxy-ethoxy)-phenyl]-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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: 89 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C
  • 33
  • [ 3951-89-1 ]
  • [ 313729-87-2 ]
YieldReaction ConditionsOperation 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
  • 34
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-cyclobutylmethyl-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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: 87 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C
  • 35
  • [ 3951-89-1 ]
  • [ 313729-92-9 ]
YieldReaction ConditionsOperation 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: 87 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C
  • 36
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-(1-methyl-1<i>H</i>-pyrazol-4-ylmethyl)-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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: 63 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 69 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C
  • 37
  • [ 3951-89-1 ]
  • [ 313751-84-7 ]
YieldReaction ConditionsOperation 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: 59 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 80 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C
  • 38
  • [ 3951-89-1 ]
  • [ 313751-95-0 ]
YieldReaction ConditionsOperation 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: 63 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 69 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C
  • 39
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-(2-methyl-2<i>H</i>-pyrazol-3-ylmethyl)-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation 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: 67 percent / triacetoxyborohydride / 1,2-dichloro-ethane / 20 °C 9: 77 percent / aq. NaOH / tetrahydrofuran; methanol / 20 °C 10: SOCl2; DMF / tetrahydrofuran / 20 °C
  • 40
  • [ 52727-57-8 ]
  • [ 3951-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 88 percent / pyridine / 1 h / 55 °C 2.1: NaH / dimethylformamide / 1 h / 20 °C 2.2: NaI / dimethylformamide / 14 h / 80 °C 3.1: 25.1 g / NaH / dimethylformamide / 15 h / 80 °C 4.1: 21 percent / H2SO4; AcOH / 2.5 h / 90 °C
Multi-step reaction with 2 steps 1.1: 5 h / 25 - 55 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / 0 - 25 °C / Inert atmosphere 2.2: 60 h / 0 - 80 °C / Inert atmosphere 2.3: 15 h / 0 - 80 °C
  • 41
  • [ 3951-89-1 ]
  • [ 123-38-6 ]
  • 7-bromo-1-propyl-2,3,4,5-tetrahydro-1H-1-benzazepine-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 6h;
  • 42
  • None [ No CAS ]
  • [ 3951-89-1 ]
YieldReaction ConditionsOperation in experiment
With sulfuric acid; acetic acid at 80℃; for 2.5h;
  • 43
  • [ 3951-89-1 ]
  • [ 108-23-6 ]
  • [ 872624-48-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane at 0℃; for 1.5h; 1.3 Step 3; Preparation of (+/-)-Isopropyl 7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[&]azepine-1-carboxylate; Add a solution of methyl 5-bromo-2-[methoxycarbonylpropyl)amino] benzoate (11.7 g,28.1 mmol) in toluene (100 mL) to a suspension of potassium tert-butoxide (6.31 g, 56.2mmol) in toluene (100 mL) at 70 °C under an atmosphere of nitrogen over a period of 30min. After 15 min, cool the mixture to room temperature and pour the suspension into icewater (500 mL). Adjust the pH of the solution to pH = 3 with 2 N hydrochloric acid (25mL) and separate the layers. Extract the aqueous layer with ethyl acetate (3 x 200 mL)and combine the organic extracts. Dry the organic layer over anhydrous sodium sulfate,filter, and remove the solvent under reduced pressure to provide (+/-)-l-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [Z7]azepine-l,4-dicarboxylate as anorange oil (10.5 g, 98% crude). Dissolve (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [&]azepine~l,4-dicarboxylate (10.5 g, 27.3 mmol) in glacialacetic acid (100 mL) and add water (10 mL) followed by concentrated hydrochloric acid(35 mL) and heat the resulting solution at reflux for 1 h. Cool the mixture to roomtemperature and pour into ice water (500 mL). Adjust the to pH = 8 with potassiumhydroxide (85 g) in water (200 mL), and extract the mixture with ethyl acetate (3 x 150mL) and combine the organic extracts. Dry the organic layer over anhydrous sodiumsulfate, filter, and remove the solvent under reduced pressure. Dissolve the crudematerial (12.0 g) in dichloromethane (30 mL) and cool to 0 °C. To the solution addpyridine (2.0 mL, 25.5 mmol) followed by dropwise addition of 1.0 M solution ofisopropyl chloroformate in toluene (19.1 mL, 19.1 mmol) and stir for 1.5 h. Pour thereaction into water (100 mL) and separate the layers. Extract the aqueous layer withdichloromethane (2 x 40 mL) and combine the organic extracts and wash with 2 Nhydrochloric acid, saturated sodium hydrogen carbonate, and brine (80 mL each). Drythe organic layer over anhydrous sodium sulfate, filter, and remove the solvent underreduced pressure. Chromatograph the residue over silica gel eluting with hexanes/ethylacetate (60:40), to afford the title compound as a yellow solid (3.5 g, 40% over threesteps).
  • 44
  • [ 872624-49-2 ]
  • [ 3951-89-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[b]azepine-1,4-dicarboxylate With hydrogenchloride; water; acetic acid for 1h; Heating / reflux; Stage #2: With potassium hydroxide In water 1.3 Step 3; Preparation of (+/-)-Isopropyl 7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo[&]azepine-1-carboxylate; Add a solution of methyl 5-bromo-2-[methoxycarbonylpropyl)amino] benzoate (11.7 g,28.1 mmol) in toluene (100 mL) to a suspension of potassium tert-butoxide (6.31 g, 56.2mmol) in toluene (100 mL) at 70 °C under an atmosphere of nitrogen over a period of 30min. After 15 min, cool the mixture to room temperature and pour the suspension into icewater (500 mL). Adjust the pH of the solution to pH = 3 with 2 N hydrochloric acid (25mL) and separate the layers. Extract the aqueous layer with ethyl acetate (3 x 200 mL)and combine the organic extracts. Dry the organic layer over anhydrous sodium sulfate,filter, and remove the solvent under reduced pressure to provide (+/-)-l-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [Z7]azepine-l,4-dicarboxylate as anorange oil (10.5 g, 98% crude). Dissolve (+/-)-1-isopropyl-4-methyl-7-bromo-5-oxo-2,3,4,5-tetrahydrobenzo [&]azepine~l,4-dicarboxylate (10.5 g, 27.3 mmol) in glacialacetic acid (100 mL) and add water (10 mL) followed by concentrated hydrochloric acid(35 mL) and heat the resulting solution at reflux for 1 h. Cool the mixture to roomtemperature and pour into ice water (500 mL). Adjust the to pH = 8 with potassiumhydroxide (85 g) in water (200 mL), and extract the mixture with ethyl acetate (3 x 150mL) and combine the organic extracts. Dry the organic layer over anhydrous sodiumsulfate, filter, and remove the solvent under reduced pressure. Dissolve the crudematerial (12.0 g) in dichloromethane (30 mL) and cool to 0 °C. To the solution addpyridine (2.0 mL, 25.5 mmol) followed by dropwise addition of 1.0 M solution ofisopropyl chloroformate in toluene (19.1 mL, 19.1 mmol) and stir for 1.5 h. Pour thereaction into water (100 mL) and separate the layers. Extract the aqueous layer withdichloromethane (2 x 40 mL) and combine the organic extracts and wash with 2 Nhydrochloric acid, saturated sodium hydrogen carbonate, and brine (80 mL each). Drythe organic layer over anhydrous sodium sulfate, filter, and remove the solvent underreduced pressure. Chromatograph the residue over silica gel eluting with hexanes/ethylacetate (60:40), to afford the title compound as a yellow solid (3.5 g, 40% over threesteps).
  • 45
  • [ 3951-89-1 ]
  • [ 124-41-4 ]
  • [ 124-63-0 ]
  • methyl 7-bromo-1-methoxycarbonyl-2,3-dihydro-1H-1-benzazepine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 7-bromo-1,2,3,4-tetrahydro-5H-1-benzazepin-5-one; sodium methylate In carbonic acid dimethyl ester for 8h; Heating / reflux; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at -15℃; for 1h; Stage #3: methanesulfonyl chloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine more than 3 stages;
  • 46
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxy-ethoxy)-phenyl]-1-propyl-2,3-dihydro-1<i>H</i>-benzo[<i>b</i>]azepine-4-carbonyl chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C
  • 47
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C 6.1: hydrogenchloride / ethyl acetate / 1 h / 20 °C
  • 48
  • [ 3951-89-1 ]
  • 7-[4-(2-butoxyethoxy)phenyl]-1-propyl-N-[4-[[N-methyl-N-(tetrahydropyran-4-yl)amino]methyl]phenyl]-2,3-dihydro-1H-1-benzazepine-4-carboxamide fumarate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C 6.1: 2-butenedioic acid / ethanol / 0.5 h / 20 °C
  • 49
  • [ 3951-89-1 ]
  • [ 313740-83-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 6 h / 20 °C 2.1: potassium carbonate / ethanol; water; toluene / 1 h / 20 °C 2.2: 3 h / Heating / reflux 3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 2 h / -78 °C 3.2: 2 h / 20 °C 4.1: thionyl chloride / N,N-dimethyl-formamide / tetrahydrofuran / 1 h / 20 °C 5.1: triethylamine / tetrahydrofuran; DMF (N,N-dimethyl-formamide) / 16 h / 0 - 20 °C
  • 50
  • [ 2969-81-5 ]
  • [ 223526-84-9 ]
  • [ 3951-89-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: methyl 5-bromo-2-[(4-methylphenylsulfonyl)amino]benzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; Stage #2: ethyl 4-bromobutanoate With sodium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 60h; Inert atmosphere; Stage #3: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 15h; 2.2 Step 2: Synthesis of compound BB-1B-3 Sodium hydrogen (6.14g, 60% purity) and DMF (50 mL) were added to a solution of BB-1B-2 (59 g) in DMF (200 mL) at 0 °C , and then stirred at 25 °C under the atmosphere of nitrogen for 2 hours, sodium iodide (23.02 g) and ethyl 4-bromobutyrate (32.95 g) were added thereto at 0 °C and stirred at 80 °C under the atmosphere of nitrogen for 16 hours, and then sodium hydrogen (6.14 g, 60% purity) and DMF (50 mL) were added thereto at 0°C and stirred at 80°C under the atmosphere of nitrogen for 15 hours. The mixture was added with water (200 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine (200 mL), dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a yellow oil. Concentrated sulfuric acid (100 mL, 98% purity) and acetic acid (157.5 g) were add to the yellow oil at 0° and stirred at 90°C for 2.5 hours. The mixture was adjusted to pH = 8 with 12 mol/L sodium hydroxide in aqueous solution and then extracted with ethyl acetate (300 mL×3), and washed with saturated brine (300 mL) to combine organic layers. The combined organic layer was dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a residue. The residue was purified with a silica gel column (petroleum ether/ethyl acetate = 50:1 to 5:1) to obtain BB-1B-3.
Stage #1: methyl 5-bromo-2-[(4-methylphenylsulfonyl)amino]benzoate With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 25℃; for 2h; Inert atmosphere; Stage #2: ethyl 4-bromobutanoate With sodium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 60h; Inert atmosphere; Stage #3: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 80℃; for 15h; 2.2 Step 2: Synthesis of compound BB-1B-3 Sodium hydrogen (6.14g, 60% purity) and DMF (50 mL) were added to a solution of BB-1B-2 (59 g) in DMF (200 mL) at 0 °C , and then stirred at 25 °C under the atmosphere of nitrogen for 2 hours, sodium iodide (23.02 g) and ethyl 4-bromobutyrate (32.95 g) were added thereto at 0 °C and stirred at 80 °C under the atmosphere of nitrogen for 16 hours, and then sodium hydrogen (6.14 g, 60% purity) and DMF (50 mL) were added thereto at 0°C and stirred at 80°C under the atmosphere of nitrogen for 15 hours. The mixture was added with water (200 mL) and extracted with ethyl acetate (50 mL×3). The combined organic layer was washed with saturated brine (200 mL), dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a yellow oil. Concentrated sulfuric acid (100 mL, 98% purity) and acetic acid (157.5 g) were add to the yellow oil at 0° and stirred at 90°C for 2.5 hours. The mixture was adjusted to pH = 8 with 12 mol/L sodium hydroxide in aqueous solution and then extracted with ethyl acetate (300 mL×3), and washed with saturated brine (300 mL) to combine organic layers. The combined organic layer was dried with anhydrous sodium sulfate, and filtered and evaporated under reduced pressure to obtain a residue. The residue was purified with a silica gel column (petroleum ether/ethyl acetate = 50:1 to 5:1) to obtain BB-1B-3.
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