HCID 86614875, compound → HCID 178458983, compound

HRID 549493Notes

Reaction equation

HRID 549493 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:34](=[CH:35][CH:36]=1)[C:12]1[N:13](COCC[Si](C)(C)C)[C:14]([C:16]3[C:23]([C:24]#[N:25])=[CH:22][CH:21]=[CH:20][C:17]=3[C:18]#[N:19])=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([CH2:37][C:38]([OH:41])([CH3:40])[CH3:39])=[CH:6][C:5]2=1>CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:34](=[CH:35][CH:36]=1)[C:12]1[NH:13][C:14]([C:16]3[C:17]([C:18]#[N:19])=[CH:20][CH:21]=[CH:22][C:23]=3[C:24]#[N:25])=[N:15][C:11]=1[C:10]1[CH:9]=[CH:8][C:7]([CH2:37][C:38]([OH:41])([CH3:39])[CH3:40])=[CH:6][C:5]2=1

Participants

3

Reactant 1

HCID 86614875HCID 86614875, compound

Product 1

HCID 178458983HCID 178458983, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

2-(9-chloro-6-(2-hydroxy-2-methylpropyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile (1.94 g) from Step 3 above was dissolved in TBAF (1 M in THF, 20 mL). The mixture was heated at reflux for 5 h and then quenched with water. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography on silica (50% ethyl acetate in hexanes) to provide 2-[9-chloro-6-(2-hydroxy-2-methylpropyl)-1H-phenanthro[9,10-d]imidazol-2-yl]isophthalonitrile (500 mg) as a yellow solid. 1H NMR δ (ppm) (400 MHz, Acetone-d6): 13.13 (1H, bs), 8.87 (1H, s), 8.77 (1H, s), 8.58 (1H, m), 8.43 (1H, m), 8.35 (2H, d, J=7.9 Hz), 7.99 (1H, t, J=7.9 Hz), 7.73 (2H, dd, J=1.9, 8.6 Hz), 3.51 (1H, bs), 3.08 (2H, s), 1.26 (6H, s).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 h
  3. customquenched with water
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by flash chromatography on silica (50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-0458fc06e02a43388cdf1535386c045e
Source dataset
uspto-grants-2011_05
Patent number
US07943649B2

Reaction notes

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