Dimethylformamide → HCID 67055850, compound

HRID 404254Notes

Reaction equation

HRID 404254 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][CH2:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[OH:16])=[CH:8][N:7]=[CH:6]1.[H-].[Na+].BrC[C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1.[CH3:30]N(C=O)C>O>[Cl:29][C:26]1[CH:25]=[CH:24][CH:23]=[CH:28][C:27]=1[CH2:30][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]1[N:5]([CH2:4][CH2:3][C:2]([CH3:18])([CH3:17])[CH3:1])[CH:6]=[N:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 44468002HCID 44468002, compound

Product 1

HCID 67055850HCID 67055850, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of 2-(1-(3,3-dimethylbutyl)-1H-imidazol-5-yl)phenol (122.0 mg, 0.5 mmol) in DMF (3 mL) at 0° C. was added NaH (36.0 mg, 0.75 mmol) portion wise. The resulting mixture was allowed to stir for 10 min and 1-(bromomethyl)-4-chlorobenzene (123.0 mg, 0.6 mmol) was added. After stirring overnight the reaction mixture was diluted with water and the aqueous phase extracted with ethyl acetate (2×10 mL). The combined organic layers were washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to afford the crude residue, which was purified by column chromatography on silica gel to afford the desired product in 30% yield. 1H NMR: 0.78 (s, 9H), 1.38-1.47 (m, 2H), 3.75-3.85 (m, 2H), 5.00 (s, 2H), 6.98-7.09 (m, 3H), 7.15 (d, 2H, J=7.6 Hz), 7.24-7.40 (m, 4H), 7.55 (s, 1H).

Workup

  1. stirringAfter stirring overnight the reaction mixture
  2. extractionthe aqueous phase extracted with ethyl acetate (2×10 mL)
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude residue, which
  7. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3ba34eb1b79845beba120f01562f757f
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Reaction notes

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