HCID 86614875, compound → HCID 178458983, compound

HRID 2117992Notes

Reaction equation

HRID 2117992 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 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=7.9Hz), 7.99 (1H, t, J=7.9 Hz), 7.73 (2H, dd, J=1.9, 8.6Hz), 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 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-90c11e106d694c53994a633d9b7f51fd
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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