Water → 5-bromo-2-methyl-4-(trifluoromethyl)-1H-indole

HRID 913495Notes

Reaction equation

HRID 913495 reaction equation
[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([CH3:11])[CH2:5]2.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.O>O1CCOCC1>[Br:1][C:2]1[C:3]([C:12]([F:14])([F:13])[F:15])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH3:11])=[CH:5]2

Participants

5

Reactant 3

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57800231HCID 57800231, compound

Product 1

HCID 578001615-bromo-2-methyl-4-(trifluoromethyl)-1H-indoleYield 62.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-bromo-2-methyl-4-(trifluoromethyl)-2,3-dihydro-1H-indole (0.09 g, 0.320 mmol; step C above) in 1,4-dioxane (5 mL) at rt was added DDQ (0.110 g, 0.48 mmol) in one portion. After 1 h, the mixture was poured into water and extracted with Et2O (×3). Combined organics were washed (1 N NaOH, H2O, brine), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.056 g of the title compound as a pale yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.07 (bs, 1H), 7.36 (m, 1H), 7.25 (d, J=5.0 Hz, 1H), 6.47 (s, 1H), 2.48 (s, 3H).

Workup

  1. extractionextracted with Et2O (×3)
  2. washCombined organics were washed (1 N NaOH, H2O, brine)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-bdd6f21844fb49b3a9a3b06ff91f84ca
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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