Allyl m-bromophenyl ether → HCID 18512295, compound

HRID 1370873Notes

Reaction equation

HRID 1370873 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1)[CH:2]=[CH2:3].C([Li])(C)(C)C.[CH2:17]([N:24]([CH2:37][C:38]1[CH:49]=[CH:48][C:41]([C:42](N(OC)C)=[O:43])=[CH:40][CH:39]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[C:26]=1[CH3:36])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[C:42]([C:41]1[CH:40]=[CH:39][C:38]([CH2:37][N:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:25]2[C:26]([CH3:36])=[C:27]([NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH:28]=[CH:29][CH:30]=2)=[CH:49][CH:48]=1)=[O:43])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 257945Allyl m-bromophenyl etherHCID 18511970HCID 18511970, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 18512295HCID 18512295, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

The product from Example 88C (0.983 g, 3.80 mmoles) in anhydrous THF (10 mL) at −78° C. was treated dropwise with 1.7 M t-butyllithium (4.46 mL, 7.59 mmoles). Reaction stirred 30 minutes at −78° C. and was then treated with the product from Example 88B (1.00 g, 1.90 mmoles. Reaction stirred 15 minutes at −78° C. and then allowed to warm to 0° C. Reaction quenched with saturated NH4Cl and warmed to room temperature. The mixture was diluted with ethyl acetate, washed with H2O, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by chromatography on a pre-packed Biotage silica gel column (30% ethyl acetate:hexanes) to provide the title compound (0.369 g, 36%). MS (ESI−) m/z 539 (M−H)−.

Workup

  1. customReaction
  2. customReaction
  3. stirringstirred 15 minutes at −78° C.
  4. temperatureto warm to 0° C
  5. customReaction
  6. customquenched with saturated NH4Cl
  7. temperaturewarmed to room temperature
  8. additionThe mixture was diluted with ethyl acetate
  9. washwashed with H2O, brine
  10. dry with materialdried (Na2SO4)
  11. filtrationfiltered
  12. concentrationthe filtrate concentrated under reduced pressure
  13. customThe residue was purified by chromatography on a pre-packed Biotage silica gel column (30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-a6db85bf35c34c1aa1abf9671abf24c2
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

Loading…