Methyl Acrylate → HCID 66917619, compound

HRID 1817992Notes

Reaction equation

HRID 1817992 reaction equation
Br[C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:17][O:16][C:12](=[O:15])/[CH:13]=[CH:14]/[C:2]1[CH:3]=[C:4]([F:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 38528797-bromo-5-fluoro-1H-indole

Product 1

HCID 66917619HCID 66917619, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 7-Bromo-5-fluoro-1H-indole [which was prepared according to the known method (Dobbs, A., J. Org. Chem., 66, 638-641 (2001)], (400 mg, 1.87 mmol) and methyl acrylate (241 mg, 2.8 mmol) in triethylamine (1.5 ml), palladium(II) acetate (43 mg, 0.19 mmol) and tri-o-tolylphosphine (170 mg, 0.56 mmol) was added under argon at rt The reaction mixture was stirred at 100° C. for 4 hrs in a sealed pressure tube and then cooled to rt The reaction mixture was diluted with CH2Cl2 (50 ml), washed with water (3×30 ml), brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by column chromatography on silica gel with EtOAc/hexane as an eluent to give 300 mg of compound I-30 as a yellow solid. 1H-NMR (500 MHz, CDCl3).

Workup

  1. customwas prepared
  2. temperaturecooled to rt The reaction mixture
  3. washwashed with water (3×30 ml), brine
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of solvent
  6. customthe residue was purified by column chromatography on silica gel with EtOAc/hexane as an eluent

Sources & evidence

ORD record
ord-24c11b3877004aeba33585871b097249
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

Loading…