N-bromobutanimide → 3-bromo-2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine

HRID 1046975Notes

Reaction equation

HRID 1046975 reaction equation
[CH2:1]([C:9]1[N:10]=[C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][C:14]3[N:22]=[CH:23][CH:24]=[CH:25][C:13]=3[N:12]2[CH:26]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:27]N1C(=O)CCC1=O>C1COCC1>[Br:27][C:26]1[N:12]2[C:13]3[CH:25]=[CH:24][CH:23]=[N:22][C:14]=3[NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:11]2=[N:10][C:9]=1[CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 1363903832-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine

Product 1

HCID 1363902423-bromo-2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepineYield 42.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution 2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.374 g, 1 eq.) in THF (50 mL) was added N-bromosuccinimide (0.206 g, 1.05 eq.). The reaction was stirred at room temperature for 30 minutes, poured onto water (100 mL) and extracted with dichloromethane (2×100 mL). The organic extracts were combined, washed with brine (1×50 mL) and dried over sodium sulfate. After filtration and concentration under reduced pressure, the crude product, 3-bromo-2-phenethyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepine (0.197 g, 42%) was obtained as an orange solid. LCMS: 419 [M+H].

Workup

  1. additionpoured onto water (100 mL)
  2. extractionextracted with dichloromethane (2×100 mL)
  3. washwashed with brine (1×50 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and concentration under reduced pressure

Sources & evidence

ORD record
ord-904adbf678214a2b8c84b0a076b987e9
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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