4-(Chloromethyl)-1-trityl-1H-imidazole → HCID 88119016, compound

HRID 1355665Notes

Reaction equation

HRID 1355665 reaction equation
[C:1]12([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:21]5[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=5)[CH:19]=4)[CH2:14][C:13]3=[O:29])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl[CH2:31][C:32]1[N:33]=[CH:34][N:35]([C:37]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:36]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1COCC1>[C:1]12([CH2:11][N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[C:18]([C:21]5[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=5)[CH:19]=4)[C:14]([CH2:31][C:32]4[N:33]=[CH:34][N:35]([C:37]([C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)([C:44]5[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=5)[C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)[CH:36]=4)([CH2:31][C:32]4[N:33]=[CH:34][N:35]([C:37]([C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)([C:44]5[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=5)[C:38]5[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=5)[CH:36]=4)[C:13]3=[O:29])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

5

Reactant 3

HCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 3251421Potassium bis(trimethylsilyl)amideHCID 18507795HCID 18507795, compound

Product 1

HCID 88119016HCID 88119016, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(1-Adamantan-1-ylmethyl-2-oxo-2,3-dihydro-1H-indol-6-yl)-benzonitrile (191 mg, 0.50 mmol) and 4-chloromethyl-1-trityl-1H-imidazole compound (449 mg, 1.25 mmol) were dissolved in 5 ml of anhydrous THF under an atmosphere of dry N2. To this solution was added 95% KHMDS (220 mg, 1.05 mmol) and the reaction mixture was subsequently stirred overnight. The reaction mixture was partitioned between DCM and saturated aqueous NaHCO3. The DCM layer was dried over Na2SO4, filtered and concentrated under vacuum to give a purple foam which was chromatographed on flash silica gel eluting with a gradient of CHCl3 to CHCl3/MeOH/NH4OH (98/2/0.01) to give 136 mg of the titled compound as a pink oil.

Workup

  1. customThe reaction mixture was partitioned between DCM and saturated aqueous NaHCO3
  2. dry with materialThe DCM layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a purple foam which
  6. customwas chromatographed on flash silica gel eluting with a gradient of CHCl3 to CHCl3/MeOH/NH4OH (98/2/0.01)

Sources & evidence

ORD record
ord-00388cb497c64678a3c20ec815e84130
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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