N-bromobutanimide → tert-Butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1714004Notes

Reaction equation

HRID 1714004 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH:9]1([C:15]2[C:23]3[C:18](=[CH:19][C:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>>[Br:1][C:16]1[NH:17][C:18]2[C:23]([C:15]=1[CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)=[CH:22][CH:21]=[C:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH:19]=2

Participants

3

Reactant 2

HCID 67184N-bromobutanimide2×HCID 68433774tert-butyl 3-cyclohexyl-1H-indole-6-carboxylate2×

Product 1

HCID 59750072tert-Butyl 2-bromo-3-cyclohexyl-1H-indole-6-carboxylateYield 57%

Procedure

N-bromosuccinimide (1.1 eq) was added portionwise over 1 h to tert-butyl 3-cyclohexyl-1H-indole-6-carboxylate in CCl4 (from Step 4, 0.07 M) with vigorous stirring. The reaction was stirred at RT for a further hour following complete addition of NBS. The CCl4 was then removed in vacuo and the residue taken up in EtOAc. The organics were washed with a saturated aqueous solution of sodium thiosulfate (twice), brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification was by flash chromatography (5-20% EtOAc/PE gradient) to yield the title compound (57%); MS (ES+) m/z 380 (M+H)+, 378 (M+H)+.

Workup

  1. customThe CCl4 was then removed in vacuo
  2. washThe organics were washed with a saturated aqueous solution of sodium thiosulfate (twice), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification

Sources & evidence

ORD record
ord-a2f621354e4a41b8af83362bbd77cf67
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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