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Synthetic route

5-bromo-2-bromoacetamido-2'-fluorobenzophenone
1647-74-1

5-bromo-2-bromoacetamido-2'-fluorobenzophenone

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
With ammonia In methanol for 16h; Heating / reflux;56.8%
With ammonia for 5h; Heating;4.5 g
With ammonia In methanol for 18h;98.6 mg
With ammonia In methanol at 0 - 20℃;68 mg
5-bromo-2'-fluoro-2-aminobenzophenone
1479-58-9

5-bromo-2'-fluoro-2-aminobenzophenone

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Stage #1: 5-bromo-2'-fluoro-2-aminobenzophenone; 2-Bromoacetyl bromide With sodium hydrogencarbonate In dichloromethane
Stage #2: With ammonia In methanol Heating / reflux;
Stage #1: 5-bromo-2'-fluoro-2-aminobenzophenone; 2-Bromoacetyl bromide With sodium hydrogencarbonate In dichloromethane
Stage #2: With ammonia In methanol Heating / reflux;
N(1)-[4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl]glycinamide
2824-08-0

N(1)-[4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl]glycinamide

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
With acetic acid In ethanol for 0.25h; Heating / reflux;
2-amino-5-bromo-N-methoxy-N-methyl-benzamide
304854-54-4

2-amino-5-bromo-N-methoxy-N-methyl-benzamide

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -100 °C / Inert atmosphere
2: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3: ammonia / methanol / 18 h
View Scheme
5-bromo-2'-fluoro-2-aminobenzophenone
1479-58-9

5-bromo-2'-fluoro-2-aminobenzophenone

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
2: ammonia / methanol / 18 h
View Scheme
Multi-step reaction with 2 steps
1: sodium carbonate / dichloromethane; water / 2 h / 0 °C
2: ammonia / methanol / 0 - 20 °C
View Scheme
5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide; dihydrogen peroxide / water / 0.5 h / 50 °C
1.2: pH Ca. 4
2.1: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -100 °C / Inert atmosphere
4.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
5.1: ammonia / methanol / 18 h
View Scheme
2-amino-5-bromobenzoic acid hydrochloride
74189-16-5

2-amino-5-bromobenzoic acid hydrochloride

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
2: n-butyllithium / tetrahydrofuran; hexane / 1 h / -100 °C / Inert atmosphere
3: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
4: ammonia / methanol / 18 h
View Scheme
7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide
10329-38-1

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide

Conditions
ConditionsYield
With peracetic acid In dichloromethane for 4.5h; Ambient temperature;80.9%
propionaldehyde
123-38-6

propionaldehyde

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

7-bromo-5-(2-fluorophenyl)-4-propyl-1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one

7-bromo-5-(2-fluorophenyl)-4-propyl-1,3,4,5-tetrahydro-2H-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
Stage #1: 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 4h;
Stage #2: propionaldehyde In methanol at 20℃;
62%
Ethyl isocyanoacetate
2999-46-4

Ethyl isocyanoacetate

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

ethyl 8-bromo-6-(2'-fluorophenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate
612526-24-6

ethyl 8-bromo-6-(2'-fluorophenyl)-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

Conditions
ConditionsYield
Stage #1: 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran at 0℃; for 0.5h;
Stage #3: Ethyl isocyanoacetate In tetrahydrofuran at 0℃; for 1h;
58%
Stage #1: 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h;
Stage #2: With diethyl chlorophosphate In tetrahydrofuran at 0℃; for 0.5h;
Stage #3: Ethyl isocyanoacetate With sodium hydride; acetic acid more than 3 stages;
7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

5-(2-fluoro-phenyl)-7-trimethylsilylacetyleno-1,3-dihydro-benzo[e][1,4]diazepin-2-one

5-(2-fluoro-phenyl)-7-trimethylsilylacetyleno-1,3-dihydro-benzo[e][1,4]diazepin-2-one

Conditions
ConditionsYield
With triethylamine; bis(triphenylphosphine) palladium (Il) acetate In acetonitrile for 3h; Heating / reflux;47%
With triethylamine In acetonitrile for 3h; Heck Reaction; Heating / reflux;47%
acetic acid hydrazide
1068-57-1

acetic acid hydrazide

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

flubromazolam
612526-40-6

flubromazolam

Conditions
ConditionsYield
Stage #1: 7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one With sodium hydride In tetrahydrofuran at 0℃; for 1h;
Stage #2: With di-morpholin-4-yl-phosphinic acid chloride In tetrahydrofuran at 0 - 20℃; for 2h;
Stage #3: acetic acid hydrazide In tetrahydrofuran; butan-1-ol at 20℃; for 2.25h; Heating / reflux;
40%
7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

Acetic acid 7-bromo-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester

Acetic acid 7-bromo-5-(2-fluoro-phenyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-3-yl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 80.9 percent / 40percent peroxyacetic acid / CH2Cl2 / 4.5 h / Ambient temperature
2: 6.5 g / 3 h / 0 °C
View Scheme
7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one
62659-65-8

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-3-hydroxy-2H-1,4-benzodiazepin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 80.9 percent / 40percent peroxyacetic acid / CH2Cl2 / 4.5 h / Ambient temperature
2: 6.5 g / 3 h / 0 °C
3: 3.3 g / 1 N NaOH / methanol / 0.5 h / 25 °C
View Scheme
7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one
2647-50-9

7-bromo-5-(2-fluorophenyl)-1,3-dihydro-2H-benzo[e][1,4]diazepin-2-one

7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine
885124-07-2

7-bromo-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;

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