Imidazole → 8-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

HRID 642764Notes

Reaction equation

HRID 642764 reaction equation
[CH:1]1[C:6]2[C:7]3[NH:8][C:9]4[C:14]([C:15]=3[CH2:16][S:17][C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:13][C:12]([OH:18])=[CH:11][CH:10]=4.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CN(C=O)C>[C:25]([Si:28]([CH3:30])([CH3:29])[O:18][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]1[C:6]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=3[S:17][CH2:16][C:15]2=1)([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 444118686,11-Dihydrothiochromeno[4,3-b]indol-8-ol

Product 1

HCID 596760598-(Tert-butyl-dimethyl-silanyloxy)-6,11-dihydro-5-thia-11-aza-benzo[a]fluorene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6,11-dihydro-5-thia-11-aza-benzo[a]fluoren-8-ol (820 mg, 3.24 mmoL) in DMF (10 mL) was treated with imidazole (331 mg, 4.862 mmoL) followed by TBSCl (733 mg, 4.862 mmoL) at room temperature. The reaction was stirred for 2 hours. The reaction mixture was then partitioned between CH2Cl2 and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to yield a brown oil. The crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent) to yield the title compound as a brown solid.

Workup

  1. customThe reaction mixture was then partitioned between CH2Cl2 and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a brown oil
  7. customThe crude material (the oil) was then purified by column chromatography (silica gel, hexanes:EtOAc 4:1 as eluent)

Sources & evidence

ORD record
ord-93bac9568d6d42e2a440fc327acbcfee
Source dataset
uspto-grants-2010_04
Patent number
US07696239B2

Reaction notes

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