Nitrogen → HCID 89501016, compound

HRID 1525358Notes

Reaction equation

HRID 1525358 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[C:4](I)[CH:3]=1.N#N.[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)=[C:4](/[CH:19]=[CH:18]/[C:17]([O:21][CH3:22])=[O:20])[CH:3]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 7294Methyl AcrylateHCID 89501076HCID 89501076, compound

Product 1

HCID 89501016HCID 89501016, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A solution of Intermediate 5B (100 g, 324.4 mmol) in ACN (1000 mL) was degassed with N2. TEA (64 mL) and methyl acrylate (60 mL) were added and the reaction was further degassed. Pd(OAc)2 (8 g, 11.8 mmol) was added and the reaction was heated to 85° C. for 18 h. The reaction was concentrated and the residue was diluted with H2O. The aqueous layer was extracted with EtOAc and the combined organics were washed with brine. Purification by silica gel chromatography gave 25 g of Intermediate 5C. MS (ESI) m/z: 283.0 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated
  2. additionthe residue was diluted with H2O
  3. extractionThe aqueous layer was extracted with EtOAc
  4. washthe combined organics were washed with brine
  5. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-bce1056cc44349c68d0088a7ff55ddea
Source dataset
uspto-grants-2015_07
Patent number
US09079929B2

Reaction notes

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