Hydrochloric Acid → HCID 178526153, compound

HRID 483405Notes

Reaction equation

HRID 483405 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13]CC)=[S:12])=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C[Si](C)(C)[O-].[K+].C(OCC)(=O)C.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[S:12])=[C:5]2[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23668039Potassium trimethylsilanolateHCID 86745392Ethyl 5-chloro-3-phenylthioindole-2-carboxylate

Product 1

HCID 178526153HCID 178526153, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 57 mg of ethyl 5-chloro-3-phenylthioindole-2-carboxylate from Preparation 5 in 1.7 mL of dry tetrahydrofuran, under argon, was added 48 mg of solid potassium trimethylsilanolate. The resultant mixture was stirred at room temperature for 20 h. Ethyl acetate and 1 N HCl were then added. The organic layer was washed with brine (2×) and dried over MgSO4. Filtration and concentration gave a yellow gum which was triturated with ether-hexane to give the title compound. 1H NMR (250 MHz, CDCl3) δ 7.09-7.18 (m, 3H), 7.20-7.25 (m, 2H), 7.30 (dd, 1H, J =8.6 and 2.0 Hz), 7.43 (d, 1H, J =2.0 Hz), 7.52 (d, 1H, J =8.6 Hz).

Workup

  1. washThe organic layer was washed with brine (2×)
  2. dry with materialdried over MgSO4
  3. filtrationFiltration and concentration
  4. customgave a yellow gum which
  5. customwas triturated with ether-hexane

Sources & evidence

ORD record
ord-07963b9156ce421c98be71b849df5d24
Source dataset
uspto-grants-1993_07
Patent number
US05225421

Reaction notes

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