3,5-Dimethylbenzyl bromide → HCID 54407387, compound

HRID 842935

Reaction equation

HRID 842935 reaction equation
[CH2:1]([NH:4][C:5](=[O:17])[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][CH:7]=1)[CH:2]=[CH2:3].CC1C=C(C=C(C)C=1)CBr>C1(C)C=CC=CC=1>[CH:1]([NH:4][C:5](=[O:17])[C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]([F:15])([F:16])[F:14])=[CH:10][CH:11]=1)=[CH:2][CH3:3]

Participants

4

Reactant 2

HCID 1413343,5-Dimethylbenzyl bromideHCID 22616308HCID 22616308, compound

Product 1

HCID 54407387HCID 54407387, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 11 (100 mg, 0.57 mmol) was combined with 3,5-dimethylbenzyl bromide (0.57 mmol) and heated in toluene to 100° C. for 2 hours. The resulting mixture was cooled and washed with aqueous sodium bicarbonate and extracted with methylene chloride. The organic extract was dried (sodium sulfate), filtered, and purified by silica gel chromatography (methylene chloride, methanol) to yield 12 (example 21) (65%). 1H NMR (400 MHz, CDCl3) δ8.57 (d, J=8.0 Hz, 1 H, Ar), 7.13 (dd, J=2.8, 9.2 Hz, 1 H, Ar), 6.99 (d, J=7.2 Hz, 1 H, Ar), 6.89 (s, 3 H, Ar), 6.85 (d, J=2.8 Hz, 1 H, Ar), 6.42 (d, J=7.2 Hz, 1 H, Ar), 5.36 (s, 2 H, CH2), 3.90 (s, 3 H, CH3O), 2.24 (s, 6 H, CH3); M/Z (ESI+) 293 ([M+H]+).

Workup

  1. temperatureThe resulting mixture was cooled
  2. washwashed with aqueous sodium bicarbonate
  3. extractionextracted with methylene chloride
  4. extractionThe organic extract
  5. dry with materialwas dried (sodium sulfate)
  6. filtrationfiltered
  7. custompurified by silica gel chromatography (methylene chloride, methanol)

Sources & evidence

ORD record
ord-555db30bd7194e9394527049c5d52385
Source dataset
uspto-grants-2002_04
Patent number
US06376530B1

Linked notes

Loading…