Sodium hydride → HCID 57541110, compound

HRID 545395Notes

Reaction equation

HRID 545395 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:17]([CH3:18])[C:16]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[C:15]([CH2:32][CH2:33][CH2:34][OH:35])[N:14]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41]Br)=[CH:39][CH:38]=1.[H-].[Na+]>CN(C=O)C>[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH2:41][O:35][CH2:34][CH2:33][CH2:32][C:15]2[N:14]=[C:13]([C:9]3[CH:10]=[CH:11][CH:12]=[C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:8]=3)[N:17]([CH3:18])[C:16]=2[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:23][CH2:22]2)=[O:20])=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 57541077HCID 57541077, compound

Product 1

HCID 57541110HCID 57541110, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.200 g (0.42 mmol) of [2-(3-hexyl-phenyl)-5-(3-hydroxy-propyl)-3-methyl-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 33) and 0.107 ml=0.162 g (0.83 mmol) of 4-fluorobenzylbromide in 5.0 ml of DMF was treated with 0.036 g (0.83 mmol) of sodium hydride (55% dispersion in mineral oil) at RT. After stirring for 125 hours, the reaction mixture was poured into crashed ice and extracted twice with CH2Cl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1) to give 0.063 g (26%) of the title compound as light yellow oil. MS: 589.0 (MH+).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with CH2Cl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 98:2 to 4:1)

Sources & evidence

ORD record
ord-963cd285dfcb43a4b0dcf08d16397562
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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