Tetrabutylammonium Fluoride → HCID 178458984, compound

HRID 549501Notes

Reaction equation

HRID 549501 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][C:27]([CH3:60])([CH3:59])[CH2:28][C:29]1[CH:30]=[CH:31][C:32]2[C:45]3[N:44]=[C:43]([C:46]4[C:51]([Br:52])=[CH:50][CH:49]=[CH:48][C:47]=4[Br:53])[NH:42][C:41]=3[C:40]3[C:35](=[CH:36][C:37]([O:54][CH2:55][CH:56]4[CH2:58][CH2:57]4)=[CH:38][CH:39]=3)[C:33]=2[CH:34]=1)(C(C)(C)C)(C)C>O>[CH:56]1([CH2:55][O:54][C:37]2[CH:36]=[C:35]3[C:40](=[CH:39][CH:38]=2)[C:41]2[NH:42][C:43]([C:46]4[C:47]([Br:53])=[CH:48][CH:49]=[CH:50][C:51]=4[Br:52])=[N:44][C:45]=2[C:32]2[CH:31]=[CH:30][C:29]([CH2:28][C:27]([CH3:60])([OH:26])[CH3:59])=[CH:34][C:33]3=2)[CH2:57][CH2:58]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178440597HCID 178440597, compound

Product 1

HCID 178458984HCID 178458984, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

TBAF (1 M in THF, 10 mL) was added to a flask containing 6-(2-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpropyl)-9-(cyclopropylmethoxy)-2-(2,6-dibromophenyl)-1H-phenanthro[9,10-d]imidazole (0.223 g, 0.31 mmol) from Step 7 above, at room temperature. The resulting solution was heated at reflux for 36 h, after which water was added to the reaction mixture. The aqueous layer was extracted with ethyl acetate, the organic layer dried over MgSO4, filtered and concentrated. The crude product was used directly in the next reaction (Step 9 below).

Workup

  1. customat room temperature
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux for 36 h
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. dry with materialthe organic layer dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was used directly in the next reaction (Step 9 below)

Sources & evidence

ORD record
ord-6a8489b1f1a6451f81a34c6694e3fea9
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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