Nitric Acid → HCID 68443004, compound

HRID 227512Notes

Reaction equation

HRID 227512 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].[N+:25]([O-])([OH:27])=[O:26]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3]([N+:25]([O-:27])=[O:26])=[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:17])=[O:18]

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 57445029HCID 57445029, compound

Product 1

HCID 68443004HCID 68443004, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 5-bromo-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxylate (56 mg, 0.13 mmol, 1.0 equiv) was dissolved in 3 mL of sulfuric acid and cooled to 0° C. A 1 mL aqueous solution of nitric acid (10 mg, 0.15 mmol, 1.15 equiv) was added dropwise and the reaction was stirred for 10 minutes at 0° C., after which an additional 1 mL aqueous solution of nitric acid (5 mg, 0.06 mmol, 0.5 equiv) was added dropwise. After stirring for 30 minutes, the reaction mixture was partitioned between ethyl acetate and water, 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 (0 to 15% ethyl acetate/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound ESI+MS: 462.0 [M+H]+.

Workup

  1. stirringAfter stirring for 30 minutes
  2. customthe reaction mixture was partitioned between ethyl acetate and water, which
  3. extractionwas extracted three times with ethyl acetate
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (0 to 15% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-4c118602bc7e4a0d897b11843a406513
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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