N-bromobutanimide → HCID 57800081, compound

HRID 1188410Notes

Reaction equation

HRID 1188410 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[C:11]([C:12]#[N:13])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.C1C(=O)N([Br:23])C(=O)C1>CN(C=O)C>[Br:23][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:11]([C:12]#[N:13])[C:3]=2[C:2]([F:14])([F:1])[F:15])[NH:7][CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 674054494-(trifluoromethyl)-1H-indole-5-carbonitrile

Product 1

HCID 57800081HCID 57800081, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cold solution of 4-(trifluoromethyl)-1H-indole-5-carbonitrile (0.047 g, 0.22 mmol) in DMF (2 mL), under N2, was added a solution of NBS (0.043 g, 0.24 mmol) in DMF (0.5 mL). The mixture was stirred in the ice bath for 30 min and then at rt for 1 h. The mixture was partitioned between Et2O and an aqueous solution of Na2S2O3. The organic phase was washed with water and sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by radial chromatography (5-50% EtOAc-hexanes gradient) to afford the title compound: 1H NMR (400 MHz, CDCl3+few drops of CD3OD) δ 11.52 (bs, 1H), 7.61 (d, J=8.5 Hz, 1H), 7.48-7.45 (m, 2H).

Workup

  1. customThe mixture was partitioned between Et2O
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by radial chromatography (5-50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-21ff18ecf9c04c309afedf09e0f5bba7
Source dataset
uspto-grants-2014_03
Patent number
US08673948B2

Reaction notes

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