Ethylamine → HCID 53360789, compound

HRID 2265288Notes

Reaction equation

HRID 2265288 reaction equation
C(N)C.[C:4]([NH:7][C:8](=[CH:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Br:20])[CH:14]=1)[C:9]([OH:11])=[O:10])(=[O:6])[CH3:5]>CO.C1CC=CCCC=C1.C1CC=CCCC=C1.C(F)(F)(F)S([O-])(=O)=O.[Rh]>[C:4]([NH:7][C@@H:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Br:20])[CH:14]=1)[C:9]([OH:11])=[O:10])(=[O:6])[CH3:5]

Participants

5

Reactant 2

HCID 6341EthylamineHCID 687738442-(Acetylamino)-3-(3-bromo-4-fluorophenyl)-2-propenoic acid

Product 1

HCID 53360789HCID 53360789, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 5702638Bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonateCatalystHCID 887MethanolSolvent

Procedure

A mixture of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (0.11 g, 0.18 mmol) and (R)—N-diphenylphosphino-N-methyl-1-[(S)-2-diphenylphosphino)ferrocenyl]ethylamine [(R)-methyl BoPhoz; 70 mg, 0.15 mmol] in MeOH (150 mL) under N2 was stirred for 30 min. 2-Acetylamino-3-(3-bromo-4-fluoro-phenyl)-acrylic acid (4.5 g, 15 mmol) was added, and the mixture was stirred under H2 (40 psi) on a Parr apparatus for 18 h. The mixture was concentrated to give the title compound as an orange oil (4.5 g, 100%). MS (ESI−): mass calcd. for C11H11BrFNO3, 303.0; m/z found, 301.8 [M−H]−. 1H NMR (400 MHz, DMSO-d6): 7.50 (dd, J=6.7, 2.1, 1H), 7.24 (ddd, J=8.4, 4.7, 2.2, 1H), 7.13 (t, J=8.6, 1H), 4.65 (dd, J=9.0, 5.2, 1H), 3.19 (dd, J=14.0, 5.2, 1H), 2.93 (dd, J=14.0, 9.0, 1H), 1.93 (s, 3H).

Workup

  1. stirringthe mixture was stirred under H2 (40 psi) on a Parr apparatus for 18 h
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-7bca09e237b242d38fc51f1e37f1726e
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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