Triethylsilane → Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate

HRID 656008Notes

Reaction equation

HRID 656008 reaction equation
[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[S:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:29]=1)[NH:26][CH:25]=[CH:24]2.C([SiH](CC)CC)C>C(Cl)Cl>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:16]1[CH2:17][CH2:18][S:13][CH2:14][CH2:15]1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 66173Tetrahydrothiopyran-4-oneHCID 59332585Ethyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 59332655Ethyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TMSOTf (3.38 mL, 18.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran-4-one (2.17 g, 18.7 mmol) in DCM (100 mL) at 0° C. (bath temp) under nitrogen. A solution of ethyl 5-bromo-1H-indole-7-carboxylate (5 g, 18.7 mmol) in DCM (30 mL) was then added and the reaction was stirred for 30 min. Triethylsilane (4.47 mL, 28.1 mmol) was added and the reaction was allowed to warm to room temperature overnight. The reaction mixture was washed with saturated aqueous Na2CO3 (1×100 mL, and the organic layer was dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH, giving 4.92 g (72%) of the title compound.

Workup

  1. washThe reaction mixture was washed with saturated aqueous Na2CO3 (1×100 mL
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. washThe residue was washed with MeOH

Sources & evidence

ORD record
ord-bf3fb792858d4bb883aa17b6efc97696
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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