Allyl bromide → HCID 59588984, compound

HRID 1969322Notes

Reaction equation

HRID 1969322 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8]/[CH:9]=[C:10](/[F:13])\[CH2:11]Br)([CH3:4])([CH3:3])[CH3:2].[CH:15]1([NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C>CN(C=O)C.O>[CH:15]1([NH:21][C:22]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:11]/[C:10](/[F:13])=[CH:9]\[CH2:8][NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:25][CH:24]=2)=[O:30])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 726575HCID 726575, compoundHCID 23394355HCID 23394355, compound

Product 1

HCID 59588984HCID 59588984, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A stirred solution of (E)-tert-butyl-N-(3-fluoro-4-bromobut-2-enyl)carbamate (3.48 g, 13 mmol), N-cyclohexyl-4-hydroxybenzamide (3.55 g, 16.2 mmol) and potassium carbonate (2.76 g, 20 mmol) in DMF (10 mL) under nitrogen was heated at 60° C. for 3 hours at which time TLC analysis showed no remaining allyl bromide. The reaction mixture was allowed to cool and then water (50 mL) added, causing a white precipitate to form. Stirred for 30 minutes, then filtered, washing with water to remove any remaining DMF from the filtercake. The precipitate was then taken up into dichloromethane (150 mL), filtered to remove any insolubles and then washed with NaOH solution (2 M; 20 mL) and brine (20 mL). Dried over MgSO4, filtered and the solvent removed under reduced pressure to afford the title compound as a white solid (4.23 g, 80%); 1H-NMR (400 MHz, CDCl3): δppm: 1.21-1.25 (3H, m), 1.40-1.46 (2H, m), 1.44 (9H, s), 1.61-1.69 (1H, m), 1.73-1.77 (2H, m), 2.01-2.05 (2H, m), 3.80 (2H, t, J 6.7 Hz), 3.96 (1H, m), 4.64 (1H, br s), 4.73 (2H, d, J 19.0 Hz), 5.46 (1H, dt J 18.9, 8.1 Hz), 5.81 (1H, br s), 6.96 (2H, d, J 8.3 Hz), 7.73 (2H, d, J 8.3 Hz).

Workup

  1. temperatureto cool
  2. customto form
  3. filtrationfiltered
  4. washwashing with water
  5. customto remove any remaining DMF from the filtercake
  6. filtrationfiltered
  7. customto remove any insolubles
  8. washwashed with NaOH solution (2 M; 20 mL) and brine (20 mL)
  9. dry with materialDried over MgSO4
  10. filtrationfiltered
  11. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-98624a21b8974c1a8684895cac467cc1
Source dataset
uspto-grants-2013_04
Patent number
US08426587B2

Reaction notes

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