Hydrochloric Acid → HCID 68444970, compound

HRID 227487Notes

Reaction equation

HRID 227487 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-])=O)[NH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[S:19]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)(=[O:21])=[O:20].Cl>C(O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:5]2[S:19]([N:22]1[CH2:23][CH2:24][O:25][CH2:26][CH2:27]1)(=[O:20])=[O:21]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68442892HCID 68442892, compound

Product 1

HCID 68444970HCID 68444970, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

Ethyl 5-bromo-6-nitro-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxylate (256 mg, 0.55 mmol, 1.0 equiv) was suspended in 10 mL of absolute ethanol. 1.5 mL of concentrated aqueous HCl was added, followed Zn dust (362 mg, 5.5 mmol, 10 equiv), and the reaction was stirred at ambient temperature for 1 hour. The mixture was partitioned between ethyl acetate and water, which was extracted three times with ethyl acetate. The combined organic layers were washed once with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 30% ethyl acetate/dichloromethane) provided the titled compound. Proton NMR for the product was consistent with the titled compound. 1H NMR (500 MHz, DMSO-d6): δ 12.38 (s, 1H), 8.15 (br s, 1H), 8.05 (br s, 1H), 7.91 (s, 1H), 6.94 (s, 1H), 3.62 (m, 4H), 2.87 (m, 4H) ppm. ESI+MS: 431.2 [M+H]+.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water, which
  2. extractionwas extracted three times with ethyl acetate
  3. washThe combined organic layers were washed once with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (0 to 30% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-bf5cb444089544a1bc273b33f7c46e2b
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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