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

HRID 387292Notes

Reaction equation

HRID 387292 reaction equation
[S:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:21][O:22][C:23]([C:25]1[CH:26]=[C:27]([Br:34])[CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]2)=[O:24].[SiH](CC)(CC)CC>C(Cl)Cl>[Br:34][C:27]1[CH:28]=[C:29]2[C:33](=[C:25]([C:23]([O:22][CH3:21])=[O:24])[CH:26]=1)[NH:32][CH:31]=[C:30]2[CH2:7][CH:4]1[CH2:3][CH2:2][S:1][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 20143720Thiane-4-carbaldehydeHCID 24728848methyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 59332720Methyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-ylmethyl)-1H-indole-7-carboxylateYield 44.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tetrahydro-thiopyran-4-carbaldehyde (1.3 g, 9.84 mmol) in DCM (20 mL) was added TMSOTf (3.5 mL, 19.7 mmol) at 0° C. To this mixture 5-Bromo-1H-indole-7-carboxylic acid methyl ester (2.5 g, 9.84 mmol) was added. After 2 hours, Et3SiH (6.2 mL, 39.4 mmol) was added at 0° C., and stirring continued for 18 hours. The reaction mixture was quenched with sodium bicarbone solution and extracted with DCM. The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 1.6 g (44%) of the title compound.

Workup

  1. waitcontinued for 18 hours
  2. customThe reaction mixture was quenched with sodium bicarbone solution
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-edd31a51fde443dbb27bd1bebdc3c5cf
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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