N-bromobutanimide → HCID 68486193, compound

HRID 1874953Notes

Reaction equation

HRID 1874953 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH3:9][C:10]([Si:13]([CH3:33])([CH3:32])[O:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:21]2)([CH3:12])[CH3:11]>CN(C=O)C>[Br:8][C:21]1[C:20]2[C:24](=[CH:25][CH:26]=[C:18]([O:17][CH2:16][CH2:15][O:14][Si:13]([C:10]([CH3:11])([CH3:9])[CH3:12])([CH3:33])[CH3:32])[CH:19]=2)[NH:23][C:22]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 68483846HCID 68483846, compound

Product 1

HCID 68486193HCID 68486193, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NBS (0.137 g, 0.771 mmol) was added to ethyl 5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-2-carboxylate (0.255 g, 0.701 mmol) dissolved in DMF (2 mL) and the resulting mixture was stirred overnight at RT. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, dried over MgSO4, filtered and the solvent evaporated. Purification was accomplished by silica gel column chromatography (0 to 50% EtOAc/hexanes) to afford the title compound (0.121 g, 39%) as an oily solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.90 (br. s., 1H), 7.27 (d, 1H), 7.02-7.07 (m, 1H), 7.01 (s, 1H), 4.43 (q, 2H), 4.11 (t, 2H), 4.00 (t, 2H), 1.43 (t, 3H), 0.91 (s, 9H), 0.11 (d, 6H). LC-MS (ES+) m/z 442.2 [M+H].

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. customPurification

Sources & evidence

ORD record
ord-287514f071d944f78920bbc706b5daab
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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