HCID 59424565, compound → HCID 59424466, compound

HRID 1261315Notes

Reaction equation

HRID 1261315 reaction equation
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[C:6]2[NH:13][CH:12]=[CH:11][C:7]=2[N:8]=[CH:9][N:10]=1.[H][H]>CO.Cl[Pd]Cl>[N:8]1[C:7]2[CH:11]=[CH:12][NH:13][C:6]=2[C:5]([O:4][C:3]2[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=2[F:1])=[N:10][CH:9]=1

Participants

5

Reactant 2

HCID 59424565HCID 59424565, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59424466HCID 59424466, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of 243 (263 mg, 0.966 mmol, scheme 54) in MeOH (10 mL) and PdCl2 (1.8 mg, 0.01 mmol) was stirred in the atmosphere of hydrogen for 60 hrs. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Water was added to the residue and the aqueous solution was extracted with DCM. The extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure, to afford title compound 247 (170 mg, 72% yield, crude) as a gray solid. MS (m/z): 243.08 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe aqueous solution was extracted with DCM
  5. dry with materialThe extract was dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-671cbe49ba5b48a2a115ddae95a3bb5a
Source dataset
uspto-grants-2013_06
Patent number
US08470850B2

Reaction notes

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