Methyl iodide → HCID 18370572, compound

HRID 1508456Notes

Reaction equation

HRID 1508456 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:13])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.[CH2:14]1CCN2C(=NCCC2)CC1.IC>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:13])[C:10]([O:12][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5987583-(4-Bromophenyl)-2-oxopropanoic acid

Product 1

HCID 18370572HCID 18370572, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-bromophenyl)-2-oxopropionic acid (70.0 mg, 0.288 mmol) in DMF (2 mL) at 0° C. was added DBU (72.2 mg, 0.288 mmol) and iodomethane (204 mg, 1.440 mmol). The reaction mixture was stirred for 2.5 hours at the same temperature. The reaction was acidified with 1 M HCl and extraction with ether (3×25 mL), drying (MgSO4), concentrated under reduced pressure and dried on vacuum to get the light brown oily compound B18 in 68% yield and used as such in next step.

Workup

  1. extractionThe reaction was acidified with 1 M HCl and extraction with ether (3×25 mL)
  2. dry with materialdrying (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customdried on vacuum
  5. customto get the light brown oily compound

Sources & evidence

ORD record
ord-6c5e002b21bf42f2aa01a08b05c71c8b
Source dataset
uspto-grants-2015_12
Patent number
US09221860B2

Reaction notes

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