Allyl bromide → HCID 89498376, compound

HRID 1430326Notes

Reaction equation

HRID 1430326 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([OH:17])[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[CH2:10]2)[C:6]=1[CH3:7].[H-].[Na+].Br[CH2:21][CH:22]=[CH2:23]>CN(C)C=O>[CH2:23]([O:17][C:9]1([CH2:8][N:5]2[C:6]([CH3:7])=[C:2]([Br:1])[CH:3]=[N:4]2)[CH2:14][CH2:13][CH2:12][C:11]([CH3:15])([CH3:16])[CH2:10]1)[CH:22]=[CH2:21]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 89498386HCID 89498386, compound

Product 1

HCID 89498376HCID 89498376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cold (0° C.) solution of EXAMPLE 185B (3.63 g) in N,N-dimethylformamide (25 mL) was added NaH (0.964 g, 60% dispersion in mineral oil), and the reaction was stirred for 30 minutes. 3-Bromoprop-1-ene (1.529 mL) was added. The cooling bath was removed, and the reaction was warmed to room temperature. The reaction mixture was heated to 50° C., whereupon a significant evolution of gas occurred. After 2 hours, the reaction mixture was diluted with diethyl ether (75 mL), washed with water (2×50 mL) and brine (50 mL), dried over magnesium sulfate, filtered, and concentrated. Purification of the residue by silica gel chromatography, eluting with a gradient of 1.5% to 15% ethyl acetate in hexanes, gave the title compound.

Workup

  1. customThe cooling bath was removed
  2. temperatureThe reaction mixture was heated to 50° C., whereupon a significant evolution of gas
  3. waitAfter 2 hours
  4. additionthe reaction mixture was diluted with diethyl ether (75 mL)
  5. washwashed with water (2×50 mL) and brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by silica gel chromatography
  10. washeluting with a gradient of 1.5% to 15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-aec1f9349e274a0aa4e3926486929a1e
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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