N-bromobutanimide → HCID 68444927, compound

HRID 227510Notes

Reaction equation

HRID 227510 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[S:16]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)(=[O:18])=[O:17].[Br:25]N1C(=O)CCC1=O>CN(C)C=O>[NH2:1][C:2]1[C:3]([Br:25])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[S:16]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57445042HCID 57445042, compound

Product 1

HCID 68444927HCID 68444927, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxylate (189 mg, 0.53 mmol, 1.0 equiv) was dissolved in 4 mL of dimethylformamide and cooled to 0° C. N-bromosuccinimide (95 mg, 0.54 mmol, 1.0 equiv) was added and the reaction was stirred for 15 minutes. The reaction mixture was partitioned between dichloromethane and aqueous saturated NaHCO3, which was extracted three times with dichloromethane. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 50% ethyl acetate/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 432.1 [M+H]+.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane and aqueous saturated NaHCO3, which
  2. extractionwas extracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (0 to 50% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-ccaee8d388474a3fba057135f8f81bba
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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