Triethylsilane → 5-bromo-3-(2,2-dimethyltetrahydro-thiopyran-4-yl)-1H-indole-7-carboxylic acid methyl ester

HRID 387279Notes

Reaction equation

HRID 387279 reaction equation
[CH3:1][C:2]1([CH3:9])[CH2:7][C:6](=O)[CH2:5][CH2:4][S:3]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28]([Br:35])[CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2)=[O:25].[SiH](CC)(CC)CC>C(Cl)Cl>[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28]([Br:35])[CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[C:31]2[CH:6]1[CH2:5][CH2:4][S:3][C:2]([CH3:9])([CH3:1])[CH2:7]1)=[O:25]

Participants

6

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 2875642,2-Dimethyltetrahydro-4h-thiopyran-4-oneHCID 24728848methyl 5-bromo-1H-indole-7-carboxylate

Product 1

HCID 593327645-bromo-3-(2,2-dimethyltetrahydro-thiopyran-4-yl)-1H-indole-7-carboxylic acid methyl esterYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,2-Dimethyl-tetrahydro-thiopyran-4-one (7.9 g, 55.1 mmol) in DCM (100 mL) was added TMSOTf (10 mL, 55.1 mmol) and 5-Bromo-1H-indole-7-carboxylic acid methyl ester (7.0 g, 27.6 mmol) at 0° C. After 2 hours, Et3SiH (15 mL, 110 mmol) was added at 0° C., then the mixture was stirred for 18 hours. The reaction mixture was quenched with sat. Sodium bicarbonate solution, extracted with DCM (3×100 mL). The combined organic layer was dried over MgSO4 and concentrated under vacuum. The residue was purified by column chromatography on silica gel (PE:EA=50:1 to 30:1) to give the title compound as a light yellow solid (5.5 g, 52%).

Workup

  1. customThe reaction mixture was quenched with sat. Sodium bicarbonate solution
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic layer was dried over MgSO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by column chromatography on silica gel (PE:EA=50:1 to 30:1)

Sources & evidence

ORD record
ord-edc1f7996ae340d5adc10dc3c47a1829
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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