Triethylsilane → HCID 59332568, compound

HRID 656013Notes

Reaction equation

HRID 656013 reaction equation
[S:1]1[CH2:5][CH2:4][C:3](=O)[CH2:2]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[C:27]([C:29]([O:31][CH2:32]C)=[O:30])[CH:28]=1)[NH:25][CH:24]=[CH:23]2.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:19][C:20]1[CH:21]=[C:22]2[C:26](=[C:27]([C:29]([O:31][CH3:32])=[O:30])[CH:28]=1)[NH:25][CH:24]=[C:23]2[CH:3]1[CH2:4][CH2:5][S:1][CH2:2]1

Participants

7

Reactant 5

HCID 12052TriethylsilaneHCID 61252Dihydro-3(2H)-thiophenoneHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 59332585Ethyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 59332568HCID 59332568, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To the stirred mixture of dihydro-3(2H)-thiophenone (0.167 mL, 1.97 mmol) in DCM (25 mL) under N2 was added TMS-OTf (0.71 mL, 3.9 mmol) slowly over about 5 minutes at 0° C. (ice-bath). A solution of ethyl 5-bromo-1H-indole-7-carboxylate (0.50 g, 1.97 mmol) in DCM (5 mL) was added dropwise over 60 min, then triethylsilane (1.26 mL, 9.8 mmol) was added in one portion, and the reaction was allowed to warm slowly to room temperature. Then saturated NaHCO3 and DCM were added, the layers were separated and the aqueous layer was extracted with DCM twice. The combined organic layers were dried (MgSO4) and concentrated. The residue was purified using Companion, giving 312 mg (46%) of the title compound.

Workup

  1. customthe layers were separated
  2. extractionthe aqueous layer was extracted with DCM twice
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified

Sources & evidence

ORD record
ord-b4248def0f054402a8cf8bb6443dbba8
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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