Chlorotrimethylsilane → HCID 22071489, compound

HRID 1604235Notes

Reaction equation

HRID 1604235 reaction equation
[Li]C(CC)C.C1CCCCC1.[CH2:12]([NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18]1)=[O:16])[CH3:13].CC1(C)CCCC(C)(C)N1.[CH3:36][Si:37](Cl)([CH3:39])[CH3:38]>C1COCC1>[CH2:12]([NH:14][C:15]([N:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[C:18]1[Si:37]([CH3:39])([CH3:38])[CH3:36])=[O:16])[CH3:13]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8078CyclohexaneHCID 130352,2,6,6-TetramethylpiperidineHCID 19602310HCID 19602310, compoundHCID 178418400CID 53628100

Product 1

HCID 22071489HCID 22071489, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.3M s-BuLi in cyclohexane (8.97 mL, 11.66 mmol) was added dropwise to a -78° C. cooled solution of N-(ethylaminocarbonyl)indole (1.0 g, 5.3 mmol) and 2,2,6,6-tetramethylpiperidine (0.75 g, 5.3 mmol) in THF (50 mL). After 30 min, TMSCl (0.9 g, 8 mmol) was added in a single portion, then the cold bath was removed to allow the reaction to warm over 1 h. This mixture was quenched with 25% citric acid in water (50 mL) and extracted with ethyl acetate (3 X). The organic extracts were combined, dried (MgSO4), concentrated, and recrystallized from ether/hexanes to afford 1.1 g of desired compound as a white solid, an 80% yield. m.p. 96-99° C.

Workup

  1. customthe cold bath was removed
  2. customthe reaction
  3. temperatureto warm over 1 h
  4. customThis mixture was quenched with 25% citric acid in water (50 mL)
  5. extractionextracted with ethyl acetate (3 X)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customrecrystallized from ether/hexanes

Sources & evidence

ORD record
ord-1485711b6f794a6298cbd8b96ce02018
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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