HCID 68292996, compound → HCID 68293341, compound

HRID 1504972Notes

Reaction equation

HRID 1504972 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]1[N:15]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH:16]=[CH:17][N:18]=1>CCOC(C)=O.[Pd]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][CH2:12][CH2:13][C:14]2[N:15]([C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH:16]=[CH:17][N:18]=2)=[C:2]([F:1])[CH:7]=1

Participants

4

Reactant 1

HCID 68292996HCID 68292996, compound

Product 1

HCID 68293341HCID 68293341, compoundYield 72.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 123 (150 mg, 0.43 mmol) in EtOAc (10 mL) was added Pd/C (25 mg, 10%) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 balloon at room temperature for 2 h. The suspension was filtered and the solid was washed by EtOAc. The filtrates were concentrated to dryness to give compound 124 (100 mg, 64%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ7.28-7.32 (m, 1H), 6.93-6.98 (m, 1H), 6.82-6.86 (m, 1H), 6.30-6.40 (m, 2H), 3.02 (t, 2H, J=7.6 Hz), 2.63 (t, 2H, J=7.6 Hz), 1.97-2.09 (m, 2H), 1.62 (s, 9H).

Workup

  1. customThe suspension was degassed under vacuum
  2. custompurged with H2 several times
  3. filtrationThe suspension was filtered
  4. washthe solid was washed by EtOAc
  5. concentrationThe filtrates were concentrated to dryness

Sources & evidence

ORD record
ord-258f5db25c4948d981c8eb20fe8fd461
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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