Hydrochloric Acid → HCID 22731788, compound

HRID 2270980Notes

Reaction equation

HRID 2270980 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[N:6]([S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:5]=1)(=[O:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:33][O:34][C:35]1[CH:43]=[CH:42][CH:41]=[CH:40][C:36]=1[C:37](Cl)=[O:38].Cl>C1COCC1.O>[C:17]1([S:14]([N:6]2[C:7]3[C:12](=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=3)[C:4]([C:1](=[O:3])[CH2:2][C:37]([C:36]3[CH:40]=[CH:41][CH:42]=[CH:43][C:35]=3[O:34][CH3:33])=[O:38])=[CH:5]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 889692-Methoxybenzoyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 22731752HCID 22731752, compound

Product 1

HCID 22731788HCID 22731788, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 500 mg (1.5 mmol) of 3-acetyl-1-benzenesulfonyl-5-chloroindole in THF (5 ml) was cooled at −78° C. Subsequently, to the reaction mixture was added 1.8 ml (1.8 mmol) of 1M LHMDS in THF. The solution was gradually warmed to 0° C. and cooled again to −78° C. To the solution was added 310 mg (1.8 mmol) of 2-methoxybenzoylchloride. The reaction mixture was warmed to room temperature. After 30 minutes, the mixture was treated with water and acidified with 6 N hydrochloric acid. The mixture was extracted with ethyl acetate and washed with water, and then dried. The solvent was removed and the obtained residue was chromatographed on silica gel with ethyl acetate-n-hexane as eluent. The fraction of the objective was concentrated to give 160 mg of the titled compound as a foam. Yield: 23%.

Workup

  1. temperaturecooled again to −78° C
  2. temperatureThe reaction mixture was warmed to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. customThe solvent was removed
  7. customthe obtained residue was chromatographed on silica gel with ethyl acetate-n-hexane as eluent
  8. concentrationThe fraction of the objective was concentrated

Sources & evidence

ORD record
ord-fb8531962773402c8883bf7e7ac9b308
Source dataset
uspto-grants-2001_12
Patent number
US06333323B1

Reaction notes

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