Sodium hydride → HCID 57801499, compound

HRID 2101508Notes

Reaction equation

HRID 2101508 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[CH:10]=[CH:11][N:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[N:7]([C:8]1[N:9]([CH2:13][C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[CH:10]=[CH:11][N:12]=1)[CH2:30][C:29]1[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 680214-Fluorobenzyl bromideHCID 57801506HCID 57801506, compound

Product 1

HCID 57801499HCID 57801499, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-yl]-carbamic acid tert-butyl ester was dissolved in anhydrous DMF and NaH was added. The mixture was stirred at room temperature for 10 min and 4-fluorobenzyl bromide was added. The reaction mixture was stirred at room temperature for another 1 h. The reaction was quenched with water and extracted with EtOAc (×3). The combined organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using CH2Cl2:MeOH 95:5 as an eluent to afford [1-(3,5-dichloro-benzyl)-1H-imidazol-2-yl]-(4-fluoro-benzyl)-carbamic acid tert-butyl ester (50 mg, 76%); LCMS m/z 450 [C22H22Cl2FN3O2+H]+.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for another 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc (×3)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-e9e3b7b7bc8d4ebf841e0cbfe4a766ab
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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