Sodium → 7-Bromo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

HRID 1485384Notes

Reaction equation

HRID 1485384 reaction equation
[Na].[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][C:4]=1[NH:10][CH2:11][CH2:12][C:13]([O:15]C)=O>CO>[Br:9][C:6]1[CH:7]=[CH:8][C:3]2[NH:2][C:13](=[O:15])[CH2:12][CH2:11][NH:10][C:4]=2[CH:5]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 65343583HCID 65343583, compound

Product 1

HCID 105380607-Bromo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-oneYield 24%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium (2.4 g, 104 mmol) was added in portions to 50 mL of methanol until it dissolved. The solution was then added dropwise to a cooled solution of methyl 3-((2-amino-5-bromophenyl)amino)propanoate (9.4 g, 34.6 mmol) in 50 mL of methanol at 0° C. After additional, the mixture was stirred at room temperature overnight. It was concentrated, added with water (50 mL), extracted with ethyl acetate (50 mL) and purified by CombiFlash (PE:EA=5:1) to give 7-bromo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (2 g, yield 24%). LRMS (M+H)+: 240 m/z. 1H NMR (300 MHz, CDCl3) δ 2.68-2.72 (t, J=6.0 Hz, 2H), 3.68-3.72 (t, J=6.0 Hz, 2H), 6.79-6.82 (d, J=8.7 Hz, 2H), 6.98-7.06 (m, 2H), 8.00 (br, 1H).

Workup

  1. dissolutiondissolved
  2. concentrationIt was concentrated
  3. additionadded with water (50 mL)
  4. extractionextracted with ethyl acetate (50 mL)
  5. custompurified by CombiFlash (PE:EA=5:1)

Sources & evidence

ORD record
ord-f4506d049d724f91b764d6c5485230bb
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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