Isopropyl iodide → HCID 19879222, compound

HRID 1885588Notes

Reaction equation

HRID 1885588 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[H-].[Na+].[CH3:26][CH:27](I)[CH3:28]>CN(C)C=O>[CH3:26][CH:27]([O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[C:12]3[CH2:23][CH2:22][CH2:21][N:13]3[C:14]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)[CH3:28]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 24758Sodium hydride2×HCID 136403394HCID 136403394, compound

Product 1

HCID 19879222HCID 19879222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 0.90 g (2.0 mmoles) of 2-(4-hydroxyphenyl)-3-(4-pyridyl)-6,7-dihydro-[5H]-pyrrolo[1,2-a]imidazole dihydrobromide of Example 10 in 20 ml of dry dimethylformamide cooled in an ice bath was treated with 267 mg (6.67 mmoles) of 60% sodium hydride dispersion and allowed to warm to room temperature. A solution of 374 mg. (2.22 mmoles) of 2-propyl iodide in 2 ml of dimethylformamide was added dropwise and the reaction mixture heated at 100° C. for 4 hours. Another 35 mg (0.88 mmole) of 60% sodium hydride suspension was added at room temperature, followed by 113 mg (0.67 mmole) of 2-propyl iodide and the mixture heated at 100° C. for an additional 3 hours. After stirring overnight, the mixture was poured into 10 volumes of ice water and extracted three times with ethyl acetate. The organic phase was washed with water, dried over anhydrous potassium carbonate and concentrated in vacuo. The residue was flash chromatographed on silica and the fraction eluting with 2% methanol in chloroform, concentrated in vacuo, and recrystallized from ethyl acetate to afford the titled compound, mp 148°-150° C. Anal. Calcd. for C20H21N3O: C, 75.21; H, 6.63; N, 13.16. Found: C, 75.38; H, 6.58; N, 13.26.

Workup

  1. temperaturethe reaction mixture heated at 100° C. for 4 hours
  2. temperaturethe mixture heated at 100° C. for an additional 3 hours
  3. extractionextracted three times with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. concentrationconcentrated in vacuo
  7. customchromatographed on silica
  8. washthe fraction eluting with 2% methanol in chloroform
  9. concentrationconcentrated in vacuo
  10. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-170ef2e4c93d49bc9dc8eb045d945e90
Source dataset
uspto-grants-1992_09
Patent number
US05145858

Reaction notes

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