Water → HCID 178458985, compound

HRID 2118002Notes

Reaction equation

HRID 2118002 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:38](=[CH:39][CH:40]=2)[C:16]2[N:17](COCC[Si](C)(C)C)[C:18]([C:20]4[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]#[N:23])=[N:19][C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:41][C:42]([OH:45])([CH3:44])[CH3:43])=[CH:10][C:9]3=2)[CH2:3][CH2:2]1.O>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]3[C:38](=[CH:39][CH:40]=2)[C:16]2[NH:17][C:18]([C:20]4[C:27]([C:28]#[N:29])=[CH:26][CH:25]=[CH:24][C:21]=4[C:22]#[N:23])=[N:19][C:15]=2[C:14]2[CH:13]=[CH:12][C:11]([CH2:41][C:42]([OH:45])([CH3:43])[CH3:44])=[CH:10][C:9]3=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 962WaterHCID 86614884HCID 86614884, compound

Product 1

HCID 178458985HCID 178458985, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Crude 2-(9-(cyclopropylmethoxy)-6-(2-hydroxy-2-methylpropyl)-1-{[2-(trimethyl silyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile (1.37 mmol) from Step 6 above was dissolved in TBAF (1 M in THF, 10 mL) and the mixture heated at reflux for 1.5 h. Water was added, and the aqueous layer extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (70% ethyl acetate in hexanes) to afford 2-[9-(cyclopropylmethoxy)-6-(2-hydroxy-2-methylpropyl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile (240 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1.5 h
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash chromatography on silica (70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-a164d03de3b946ed813ceb233f6d38fa
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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