Triethylsilane → 5-(4,5-dihydrothiazol-5-yl)-3-(1-methylpiperidin-4-yl)-1H-indole

HRID 1457022Notes

Reaction equation

HRID 1457022 reaction equation
[S:1]1[CH:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[C:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH:20]=2)[CH2:4][N:3]=[CH:2]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[S:1]1[CH:5]([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[NH:11][CH:10]=[C:9]3[CH:15]2[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]2)[CH2:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 187971695-(4,5-dihydrothiazol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 187971845-(4,5-dihydrothiazol-5-yl)-3-(1-methylpiperidin-4-yl)-1H-indoleYield 74.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of 0.54 gm (1.8 mMol) 5-(4,5-dihydrothiazol-5-yl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 20 mL trifluoroacetic acid were added slowly 320 μL (2 mMol) triethylsilane. The reaction mixture was stirred at room temperature for 18 hours and then concentrated under reduced pressure. The residual oil was partitioned between ethyl acetate and aqueous potassium carbonate. The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The residue was crystallized from acetonitrile to provide 0.40 gm (74%) of the title compound compound as a crystalline solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residual oil was partitioned between ethyl acetate and aqueous potassium carbonate
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-74db0c35d8f44b3aa2c8838c24b55973
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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