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

HRID 1046961Notes

Reaction equation

HRID 1046961 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]4[N:20]=[CH:21][CH:22]=[CH:23][C:11]=4[N:10]3[CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:25]N1C(=O)CCC1=O>C1COCC1>[Br:25][C:24]1[N:10]2[C:11]3[CH:23]=[CH:22][CH:21]=[N:20][C:12]=3[NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:9]2=[N:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1363902582-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine

Product 1

HCID 675030133-bromo-2-phenyl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.7 g, 1 eq.) in THF (20 mL) was added N-bromosuccinimide (0.4 g, 1 eq.). The reaction was stirred at room temperature for 1 hour, poured onto water (100 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were combined, washed with saturated sodium bicarbonate (1×100 mL), water (1×50 mL), brine (1×50 mL) and dried over sodium sulfate. After filtration and concentration under reduced pressure 3-bromo-2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.85 g, 97%) was obtained which was used with no further purification. 1H NMR (DMSO-d6) 400 MHz δ 8.64 (s, 1H), 8.28 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 8.05 (dd, JA=8 Hz, JB=1.6 Hz, 1H), 8.02-7.98 (m, 1H), 7.85 (dd, JA=8 Hz, JB=1.6 Hz, 1H), 7.53-7.48 (m, J=8 Hz, 2H), 7.42-7.34 (m, 2H), 7.30-7.22 (m, 2H), 7.14-7.09 (m, 1H); LCMS: 388 [M+H].

Workup

  1. additionpoured onto water (100 mL)
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washwashed with saturated sodium bicarbonate (1×100 mL), water (1×50 mL), brine (1×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure 3-bromo-2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.85 g, 97%)
  6. customwas obtained which
  7. customwas used with no further purification

Sources & evidence

ORD record
ord-09bf1a92fe1f4e699419f96728af21b7
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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