Dimethylformamide → HCID 70654885, compound

HRID 2277635Notes

Reaction equation

HRID 2277635 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[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>CCOC(C)=O.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]>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2]([C:25](=[O:26])[NH:12][C:9]32[CH2:11][CH2:10]3)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 71743722HCID 71743722, compound

Product 1

HCID 70654885HCID 70654885, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 1-(2-bromo-5-chlorophenyl)cyclopropanamine (2 g, 8.1 mmol), Pd(dppf)Cl2 (0.2 g), DIPEA (3.1 g, 24.3 mmol) in DMF (20 mL) was stirred in an autoclave under 2 MPa of CO (g) at 130° C. for 16 hours. The reaction mixture was diluted with EtOAc (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 (700 mg, yield 44.6%) as a yellow solid. MS: 193.8 (M+H+, 1C1).

Workup

  1. washwashed with brine
  2. customThe organic layer was dried over anhy
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated under reduced pressure
  5. customto give a crude product which
  6. customwas purified by chromatography

Sources & evidence

ORD record
ord-21dc1ea6b4f14065876f832fb6cdb0c3
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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