Triethylsilane → HCID 15907921, compound

HRID 363332Notes

Reaction equation

HRID 363332 reaction equation
Cl.[CH2:2]1[CH:10]2[N:5]([CH2:6][CH:7]=[C:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[NH:13][CH:12]=3)[CH2:9]2)[CH2:4][CH2:3]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH2:2]1[CH:10]2[N:5]([CH2:6][CH2:7][CH:8]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[C:17]([F:20])[CH:18]=4)[NH:13][CH:12]=3)[CH2:9]2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 67570021HCID 67570021, compound

Product 1

HCID 15907921HCID 15907921, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The 3-(1,2,3,4,5,8-hexahydroindolizin-7-yl)-5-fluoro-1H-indole hydrochloride salt (450 mg, 1.54 mmol) was dissolved in trifluoroacetic acid (7.5 ml) forming an orange solution. The triethylsilane (197 mg, 1.7 mmol) was added and the reaction became colorless. TLC after 5 minutes showed no starting material present. The reaction was concentrated and the resulting oil poured into water and extracted with methylene chloride. The extract was washed with base, dried over sodium sulfate, and concentrated to give the product as a colorless oil.

Workup

  1. customforming an orange solution
  2. concentrationThe reaction was concentrated
  3. additionthe resulting oil poured into water
  4. extractionextracted with methylene chloride
  5. washThe extract was washed with base
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5e4d4608e0024d90a9b0cb0bd43bb5c9
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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