Ethanol → HCID 67237208, compound

HRID 1470960Notes

Reaction equation

HRID 1470960 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=3)[CH2:11][CH2:10][CH:9]2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-])=O)[CH:23]=2)=[CH:4][CH:3]=1.CCO>C1COCC1.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]([C:13]3[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=3)[NH2:19])[CH2:11][CH2:10][CH:9]2[C:22]2[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=2)[NH2:28])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 87320079HCID 87320079, compound

Product 1

HCID 67237208HCID 67237208, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of Pd/C (0.0527 g, 0.050 mmol) in THF (2 mL) was added to a solution of Example 55D (0.45 g, 1.105 mmol) in THF (7 mL)/EtOH (7 mL) under N2. The flask was flushed with H2 and stirred under 1 atm H2 for 20 hours. The reaction was filtered through a celite plug, rinsed with ˜100 mL (1:1 EtOH:THF) and solvent was removed under vacuum. The material was used without purification. MS (DCI) m/z 348 (M+H)+.

Workup

  1. customThe flask was flushed with H2
  2. filtrationThe reaction was filtered through a celite plug
  3. washrinsed with ˜100 mL (1:1 EtOH:THF) and solvent
  4. customwas removed under vacuum
  5. customThe material was used without purification

Sources & evidence

ORD record
ord-16305f74268d464b8bda0f4a3a96bb39
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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