Bromine → HCID 68444806, compound

HRID 227511Notes

Reaction equation

HRID 227511 reaction equation
[Br: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].C([O-])(=O)C.[Na+].[Br:30]Br>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Br:30])[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:17])=[O:18]

Participants

5

Reactant 3

HCID 24408Bromine3×HCID 517045Sodium AcetateHCID 57445029HCID 57445029, compound

Product 1

HCID 68444806HCID 68444806, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

Ethyl 5-bromo-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxylate (108 mg, 0.26 mmol, 1.0 equiv) and sodium acetate (64 mg, 0.78 mmol, 3.0 equiv) were dissolved in 2 mL of acetic acid. A 1 mL solution of Br2 (41 mg, 0.26 mmol, 1.0 equiv) in acetic acid was added dropwise to the mixture and was stirred for 3 hours at ambient temperature, after which the vessel was heated at 50° C. for 18 hours. An additional 1 mL solution of Br2 (41 mg, 0.26 mmol, 1.0 equiv) in acetic acid was added dropwise to the mixture and stirred at 50° C. for 90 minutes. An additional 1 mL solution of Br2 (82 mg, 0.52 mmol, 2.0 equiv) was added and the vessel was heated for 30 more minutes. The reaction mixture was partitioned between ethyl acetate and aqueous saturated NaHCO3, which was extracted three times with ethyl acetate. The combined organic layers were dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate/hexanes) provided the titled compound. Proton NMR for the product was consistent with the titled compound. ESI+MS: 496.9 [M+H]+.

Workup

  1. temperatureafter which the vessel was heated at 50° C. for 18 hours
  2. stirringstirred at 50° C. for 90 minutes
  3. temperaturethe vessel was heated for 30 more minutes
  4. customThe reaction mixture was partitioned between ethyl acetate and aqueous saturated NaHCO3, which
  5. extractionwas extracted three times with ethyl acetate
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-7d2275c53f6a4d07bb9486eb13776e7b
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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