N-bromobutanimide → 3-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

HRID 1046993Notes

Reaction equation

HRID 1046993 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:10]=1[C:9]1[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=1[NH:7][C:6]1[N:15]=[CH:16][CH:17]=[CH:18][C:5]2=1.[Br:19]N1C(=O)CCC1=O>C1COCC1>[Br:19][C:3]1[N:4]2[C:5]3[CH:18]=[CH:17][CH:16]=[N:15][C:6]=3[NH:7][C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[C:10]2=[N:1][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 675031859H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

Product 1

HCID 675039063-bromo-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepineYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine (1.19 g, 5.1 mmol) in THF (60 mL) was slowly added N-bromosuccinimide (0.90 g, 4.3 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hours, quenched with sat.NaHCO3, extracted with ethyl acetate. The organic layers were washed with brine and dried over anhydrous Na2SO4. After filtration the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography (hexane/ethyl acetate) to give a pale yellow solid (96%). 1H NMR (DMSO-d6) 400 MHz δ: 8.58 (s, 1H), 8.26 (dd, J=4.9, 1.4 Hz, 1H), 7.94 (dd, J=8.0, 1.7 Hz, 1H), 7.74 (dd, J=7.7, 1.4 Hz, 1H), 7.43 (s, 1H), 7.34 (td, J=7.7, 1.9 Hz, 1H), 7.25-7.21 (m, 2H), 7.08 (td, J=7.5, 1.2 Hz, 1H); LC/MS [M+H]: 314.

Workup

  1. customat 0° C
  2. customquenched
  3. extractionNaHCO3, extracted with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationAfter filtration the solvent
  7. customwas removed under reduced pressure
  8. customThe crude product was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-77066993abcb4f3eab07d9a9719da7fc
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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