N-bromobutanimide → HCID 59451652, compound

HRID 1874881Notes

Reaction equation

HRID 1874881 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]([Si:13]([CH3:29])([CH3:28])[O:14][C:15]1[CH:23]=[C:22]2[C:18]([CH:19]=[C:20]([C:24]([O:26][CH3:27])=[O:25])[NH:21]2)=[CH:17][CH:16]=1)([CH3:12])[CH3:11]>CN(C=O)C>[Br:8][C:19]1[C:18]2[C:22](=[CH:23][C:15]([O:14][Si:13]([C:10]([CH3:9])([CH3:11])[CH3:12])([CH3:28])[CH3:29])=[CH:16][CH:17]=2)[NH:21][C:20]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59451367HCID 59451367, compound

Product 1

HCID 59451652HCID 59451652, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (0.670 g, 3.77 mmol) was added to a solution of methyl 6-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}-1H-indole-2-carboxylate (1.15 g, 3.77 mmol) in DMF (6 mL) and stirred overnight. The reaction was partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4, filtered and concentrated. The residue was adsorbed onto silica gel and purification was accomplished by silica gel column chromatography (EtOAc/hexanes) to afford the title compound (0.246 g, 17%). 1H NMR (400 MHz, CDCl3): δ ppm 9.31 (br. s., 1H), 7.48 (d, 1H), 6.76-6.84 (m, 2H), 3.98 (s, 3H), 0.99 (s, 9H), 0.21 (s, 6H).

Workup

  1. customThe reaction was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was adsorbed onto silica gel and purification

Sources & evidence

ORD record
ord-95e73ba61c5e445c9292059a26063ea8
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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