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

HRID 656009Notes

Reaction equation

HRID 656009 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([O-])([O-])=O.[Na+].[Na+]>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

7

Reactant 5

HCID 10340Sodium CarbonateHCID 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 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TMSOTf (1.4 mL, 7.7 mmol) was added dropwise to a solution of tetrahydro-4H-thiopyran-4-one (0.88 g, 7.6 mmol) in DCM (80 mL) in the presence of molecular sieves at 0° C. (bath temp). A solution of ethyl 5-bromo-1H-indole-7-carboxylate (2 g, 7.4 mmol). in DCM (20 mL) was added and the reaction was stirred for 15 min. Triethylsilane (2 mL, 12.5 mmol) was added and the reaction was allowed to warm to room temperature overnight. Saturated aqueous Na2CO3 was added, the layers separated and the aqueous layer extracted with DCM. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The residue was washed with MeOH and dried in a vacuum oven, giving 2.07 g (76%) of the title compound.

Workup

  1. customthe layers separated
  2. extractionthe aqueous layer extracted with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with MeOH
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-efc2ca8c3bab4590989239df2026c73f
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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