Sodium hydride → HCID 86592858, compound

HRID 351255Notes

Reaction equation

HRID 351255 reaction equation
[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:6]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:5]=1)[CH3:2].[H-].[Na+].Br[CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH2:27][CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:13][CH:14]=2)[N:6]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:5]=1)[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 135737380HCID 135737380, compound

Product 1

HCID 86592858HCID 86592858, compoundYield 45.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenol (515.5 mg) in DMF (5 ml) was added sodium hydride 60% dispersion in mineral oil (79.7 mg) at 3° C. The mixture was stirred at ambient temperature for 40 minutes. To the reaction mixture was added a solution of tert-butyl (2-bromoethyl)carbamate (558 mg) in DMF (2 ml). The mixture was stirred at 60° C. for 24 hours. The reaction mixture was poured into ice water and was extracted with AcOEt. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was crystallized from AcOEt, collected and washed with IPE to give 1st crop of tert-butyl (2-{4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)carbamate (344 mg) as a white powder. The mother liqour was concentrated in vacuo and purified by silica gel column chromatography eluted with AcOEt/CHCl3=10% to give 2nd crop of tert-butyl (2-{4-[3-ethoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)carbamate (218 mg ) as a powder.

Workup

  1. stirringThe mixture was stirred at 60° C. for 24 hours
  2. extractionwas extracted with AcOEt
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was crystallized from AcOEt
  7. customcollected
  8. washwashed with IPE

Sources & evidence

ORD record
ord-26b0baf0d80145378d5169c259d68c99
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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