Ethyl Acetate → HCID 86685950, compound

HRID 2277637Notes

Reaction equation

HRID 2277637 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1([NH2:12])[CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.C[CH2:23][O:24]C(C)=O>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:8][C:5]1[CH:4]=[C:3]2[C:2]([C:23](=[O:24])[NH:12][C:9]32[CH2:11][CH2:10]3)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 71743724HCID 71743724, compound

Product 1

HCID 86685950HCID 86685950, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1-(2-bromo-5-fluoro-phenyl)-cyclopropylamine (4.2 g, 18.3 mmol), Pd(dppf)Cl2 (0.42 g), DIPEA (7 g, 54.8 mmol) in 40 mL of DMF was heated at 130° C. under 2 MPa of CO for 12 hours. After it was cooled to room temperature, EtOAc was added it was washed with brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography to give title compound (0.3 g, yield 65.2%) as a solid; meanwhile, 3.3 g of starting material was recovered.

Workup

  1. washwas washed with brine
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-a38e94bc55514618a85f46875f8f163b
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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