6-Bromoindole → 6-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indole

HRID 2192424Notes

Reaction equation

HRID 2192424 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)([O-:3])=[O:2].[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[CH:19][NH:20]2)=[CH:16][CH:15]=1>CO>[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([C:18]([CH:5]([C:6]3[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=3)[CH2:4][N+:1]([O-:3])=[O:2])=[CH:19][NH:20]2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 6764936-BromoindoleHCID 53541824-Chloro B-nitrostyrene

Product 1

HCID 674367186-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indoleYield 45.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

1-((1E)-2-Nitrovinyl)-4-chlorobenzene (0.206 g, 1.12 mmol) was added to a solution of 6-bromoindole (0.200 g, 1.02 mmol) in methanol (5 mL), followed by the addition of sufamic acid (39.6 mg, 0.40 mmol). The mixture was stirred at 80° C. for 16 hours. The mixture was concentrated then diluted with EtOAc (15 mL) and washed with H2O (15 mL). The organic layer was dried (Na2SO4), filtered and concentrated. The crude product was purified by silica gel chromatography, eluting with EtOAc/hexane (0-50%) to give 6-bromo-3-(1-(4-chlorophenyl)-2-nitroethyl)-1H-indole (0.175 g, 45.2%). 1H NMR (CDCl3, 400 MHz) δ 8.12 (s, 1H), 7.51 (s, 1H), 7.28 (d, J=8.5 Hz, 2H), 7.25-7.20 (m, 3H), 7.17 (d, J=8.5 Hz, 1H), 7.15 (s, 1H), 5.12 (t, 1H), 5.01 (q, 1H), 4.88 (q, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthen diluted with EtOAc (15 mL)
  3. washwashed with H2O (15 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with EtOAc/hexane (0-50%)

Sources & evidence

ORD record
ord-333153fb076b40d6a0a5c58f8b5d7fb9
Source dataset
uspto-grants-2012_12
Patent number
US08329709B2

Reaction notes

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