Water → HCID 178419487, compound

HRID 2383400Notes

Reaction equation

HRID 2383400 reaction equation
[C:1]1([CH:7]2[CH2:16][C:15]3[CH:14]=[N:13][C:12]4[NH:17][N:18]=[CH:19][C:11]=4[C:10]=3[C:9]3[CH:20]=[CH:21][CH:22]=[CH:23][C:8]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:24]N1C(=O)CCC1=O.O>ClCCl>[Br:24][C:19]1[C:11]2[C:10]3[C:9]4[CH:20]=[CH:21][CH:22]=[CH:23][C:8]=4[CH:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH2:16][C:15]=3[CH:14]=[N:13][C:12]=2[NH:17][N:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 46239759HCID 46239759, compound

Product 1

HCID 178419487HCID 178419487, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 7-phenyl-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline (0.018 g, 0.060 mmol) in dichloromethane (2 mL) was added N-bromosuccinimide (0.011 g, 0.063 mmol). The reaction was stirred at room temperature for 16 hours followed by addition of water (2 mL) and dichloromethane (3 mL). The organic layer was separated, dried using Na2SO4, filtered and concentrated under reduced pressure. The crude product was purified using flash column chromatography (SiO2, 10% EtOAc in hexane) to give the pure desired product, 1-bromo-7-phenyl-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline as a yellow solid (0.010 g, 44%). M.p.=176-178° C.; 1H NMR (DMSO-d6, 400 MHz) δ 9.36 (m, 1H), 8.63 (s, 1H), 8.49 (s, 1H), 7.56 (m, 2H), 7.30-7.15 (m, 6H), 4.73 (t, J=7.2 Hz, 1H), 3.42 (m, 2H); LCMS [M+H]: 377; Elemental analysis (%): C, 63.59; H, 4.10; N, 10.98. Calcd for C20H14BrN3: C, 63.85; H, 3.75; N, 11.17.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-bfe89576251c4c07840ba06b329d46d0
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

Loading…