HCID 68292797, compound → HCID 68292739, compound

HRID 1504974Notes

Reaction equation

HRID 1504974 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:16][N:17]=2)=[N:8][CH:9]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][C:13]2[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]=[CH:16][N:17]=2)=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 68292797HCID 68292797, compound

Product 1

HCID 68292739HCID 68292739, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the compound 134 (50 mg, 0.15 mmol) in EtOAc (10 mL) was added Pd/C (10 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 135 (45 mg, 99%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ8.02-8.05 (m, 1H), 7.28-7.31 (m, 1H), 6.92-7.02 (m, 2H), 6.82-6.86 (m, 1H), 3.05 (t, 2H, J=7.6 Hz), 2.81 (t, 2H, J=7.6 Hz), 2.10-2.20 (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-fc0b43d14fd543f3989de1b0ec45b784
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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