Dimethylformamide → HCID 84049453, compound

HRID 2277639Notes

Reaction equation

HRID 2277639 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([NH2:12])[CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.CN([CH:25]=[O:26])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:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[C:9]1([CH2:11][CH2:10]1)[NH:12][C:25]2=[O:26]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 57445080HCID 57445080, compound

Product 1

HCID 84049453HCID 84049453, compoundYield 26%

Reagents, catalysts & solvents 1

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

Conditions

Temperature
130 °C

Procedure

A mixture of 1-(2-bromo-4-fluorophenyl)cyclopropanamine (3.0 g, 17.4 mmol), Pd(dppf)Cl2 (0.4 g), DIPEA (5.05 g, 39.1 mmol) in DMF (40 mL) was stirred in an autoclave under 2 MPa of CO (g) at 130° C. for 16 hours. After it was cooled down to room temperature, the reaction mixture was diluted with EtOAt (300 mL) and washed with brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated under reduced pressure to give a crude product which was purified by chromatography to afford title compound (600 mg, yield 26%) as a brown solid.

Workup

  1. temperatureAfter it was cooled down to room temperature
  2. additionthe reaction mixture was diluted with EtOAt (300 mL)
  3. washwashed with brine
  4. customThe organic layer was dried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated under reduced pressure
  7. customto give a crude product which
  8. customwas purified by chromatography

Sources & evidence

ORD record
ord-5bda6e84a0d34ca4ad8af5ade6c3a6d2
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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