HCID 22401491, compound → HCID 22401477, compound

HRID 260470Notes

Reaction equation

HRID 260470 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[C:12]1[NH:13][C:14]2[C:19]([C:20]=1[S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2.[H][H]>[Pd].CO.O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][CH2:11][C:12]1[NH:13][C:14]2[C:19]([C:20]=1[S:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:18][CH:17]=[CH:16][CH:15]=2

Participants

5

Reactant 2

HCID 22401491HCID 22401491, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22401477HCID 22401477, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of trans-2-(2-benzoxazol-2-ylethenyl)-3-phenylthioindole (0.420 g, 1.14 mmol) in 1:1 methanol/tetrahydrofuran (250 mL) was stirred under 1 atmosphere of hydrogen in the presence of 10% palladium on charcoal (100 mg). Additional catalyst was added as needed to drive the reaction to completion. The catalyst was removed by filtration, and the filtrate concentrated in vacuo. The resulting solid was triturated with 10% ethyl acetate in hexane and collected by filtration to afford the title compound, mp 192°-193° C. Anal. calc. for C23H18N2OS: C, 72.80; H, 5.04; N, 7.38. Found: C, 72.78; H, 4.95; N, 7.45.

Workup

  1. additionAdditional catalyst was added
  2. customthe reaction to completion
  3. customThe catalyst was removed by filtration
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe resulting solid was triturated with 10% ethyl acetate in hexane
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0b4ea60da21441d9aa970f5e011cf48d
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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