4-(Bromoacetyl)benzonitrile → HCID 18707465, compound

HRID 1421912Notes

Reaction equation

HRID 1421912 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[OH:11][CH2:12][CH2:13][C:14]1([CH2:32][C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[NH:18][C:17](=[S:19])[N:16]([CH2:20][CH:21]2[CH2:26][CH:25]3[CH2:27][CH:23]([C:24]3([CH3:29])[CH3:28])[CH:22]2[CH3:30])[C:15]1=[O:31].[C:39]([C:41]1[CH:50]=[CH:49][C:44]([C:45](=[O:48])[CH2:46]Br)=[CH:43][CH:42]=1)#[N:40]>C1COCC1>[OH:11][CH2:12][CH2:13][C:14]1([CH2:32][C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)[C:15](=[O:31])[N:16]([CH2:20][CH:21]2[CH2:26][CH:25]3[CH2:27][CH:23]([C:24]3([CH3:29])[CH3:28])[CH:22]2[CH3:30])[C:17]([S:19][CH2:46][C:45]([C:44]2[CH:49]=[CH:50][C:41]([C:39]#[N:40])=[CH:42][CH:43]=2)=[O:48])=[N:18]1

Participants

5

Reactant 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 3251421Potassium bis(trimethylsilyl)amideHCID 21266561HCID 21266561, compound

Product 1

HCID 18707465HCID 18707465, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Potassium bis-(trimethylsilyl)amide (286 mg, 1.43 mMol) was dissolved in anhydrous THF (20 mL) under an atmosphere of dry N2. The mixture was cooled to -40° C. and then 5-(2-hydroxy-ethyl)-5-pyridin-4-ylmethyl-2-thioxo-3-((+)-(2,6,6-trimethyl-bicyclo[3.1.1]hept-3-ylmethyl))-imidazolidin-4-one (548 mg, 1.37 mMol) was added. The mixture was warmed to ambient temperature and 4-cyanophenacyl bromide (350 mg, 1.43 mMol) was added. The reaction mixture was stirred for one hour after which time it was partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution. The CH2Cl2 layer was dried over Na2SO4, filtered and concentrated under vacuum to give a red foam. The foam was chromatographed on flash silica gel eluting with EtOAc-hexanes (50:50) to give 700 mg of the titled compound as a yellow foam as a 1:1 mixture of diastereomers.

Workup

  1. temperatureThe mixture was warmed to ambient temperature
  2. customwas partitioned between CH2Cl2 and saturated aqueous NaHCO3 solution
  3. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto give a red foam
  7. customThe foam was chromatographed on flash silica gel eluting with EtOAc-hexanes (50:50)

Sources & evidence

ORD record
ord-66208107e32a4e408695b64f8ea9f86d
Source dataset
uspto-grants-2000_06
Patent number
US06080769

Reaction notes

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