Imidazole → 6-{[tris(1-methylethyl)silyl]oxy}spiro[1-benzofuran-3,3'-indol]-2'(1'H)-one

HRID 422857Notes

Reaction equation

HRID 422857 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:18][O:19][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:10][C:9]3=[O:17].N1C=CN=C1.[CH:25]([Si:28](Cl)([CH:32]([CH3:34])[CH3:33])[CH:29]([CH3:31])[CH3:30])([CH3:27])[CH3:26]>CN(C)C=O>[CH3:26][CH:25]([Si:28]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[O:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3([CH2:18][O:19][C:4]=2[CH:3]=1)[C:16]1[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH:10][C:9]3=[O:17])[CH3:27]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 59352621HCID 59352621, compound

Product 1

HCID 452801626-{[tris(1-methylethyl)silyl]oxy}spiro[1-benzofuran-3,3'-indol]-2'(1'H)-oneYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-hydroxyspiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (3.0 g, 11.8 mmol) in anhydrous N,N-dimethylformamide (30 mL) under nitrogen were added imidazole (1.97 g, 28.9 mmol) and triisopropylsilyl chloride (6.03 mL, 28.5 mmol). The reaction mixture was stirred at ambient temperature for 16 h. The reaction mixture was concentrated in vacuo to dryness. The residue was extracted with ethyl acetate (2×50 mL), the combined organic solution was dried over sodium sulfate, and filtered. The filtrate was concentrated and purified by flash chromatography with 30% ethyl acetate in hexanes to afford 6-{[tris(1-methylethyl)silyl]oxy}spiro[1-benzofuran-3,3′-indol]-2′(1′H)-one (2.68 g, 69% yield) as colorless solid: 1H NMR (300 MHz, CDCl3) δ 8.48-8.08 (br, 1H), 7.29-6.90 (m, 4H), 6.10 (d, J=8.1 Hz, 1H), 6.50 (d, J=2.1 Hz, 1H), 6.35 (dd, J=8.1, 2.1 Hz, 1H), 4.96 (d, J=9.0 Hz, 1H), 4.69 (d, J=9.0 Hz, 1H), 1.34-0.98 (m, 21H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to dryness
  2. extractionThe residue was extracted with ethyl acetate (2×50 mL)
  3. dry with materialthe combined organic solution was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by flash chromatography with 30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5657a2ad221643aba6aa4ff54fc930f3
Source dataset
uspto-grants-2012_01
Patent number
US08101647B2

Reaction notes

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