HCID 68851145, compound → HCID 68891880, compound

HRID 1821039Notes

Reaction equation

HRID 1821039 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([O:25]C(C)(C)C)=[O:24])=[CH:17][C:16]=3[CH3:30])[N:11]=2)=[CH:6][C:5]=1[CH:31]=[CH2:32])[CH3:2].[H][H]>CO.C(OCC)(=O)C.[Pd]>[CH2:31]([C:5]1[CH:6]=[C:7]([C:10]2[S:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:17][C:16]=3[CH3:30])[N:11]=2)[CH:8]=[CH:9][C:4]=1[O:3][CH2:1][CH3:2])[CH3:32]

Participants

6

Reactant 2

HCID 68851145HCID 68851145, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68891880HCID 68891880, compoundYield 45.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-Butyl 3-(4-(5-(4-ethoxy-3-vinylphenyl)-1,2,4-thiadiazol-3-yl)-3-methylphenyl)propanoate (0.01 g, 0.025 mmol) in methanol (1.5 mL) and ethyl acetate (1.5 mL) was degassed with nitrogen. 10% Palladium/Carbon (0.01 g) was added to the reaction mixture which was stirred under a balloon of hydrogen for 30 min. The reaction was filtered through a disposable frit and concentrated in vacuo. The resulting oil was dissolved in 20% solution of trifluoroacetic acid in dichloromethane (4 mL) and stirred at rt for 2 h after which the reaction was concentrated in vacuo. Silica gel chromatography eluting with 2% methanol/methylene chloride afforded 4.5 mg of the title compound: 1H NMR (500 MHZ, CDCl3) δ 7.86 (s, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.23 (s, 1H), 7.19 (d, J=7.5 Hz, 1H), 6.93 (d, J=8.2 Hz, 1H), 4.20-4.30 (m, 2H), 3.00-3.08 (m, 2H), 2.70-2.79 (m, 4H), 2.65 (s, 3H), 1.48-1.52 (m, 3H), 1.23-1.32 (m, 3H), ESI-MS (m/z) 453.3; HPLC A: 4.68 min.

Workup

  1. filtrationThe reaction was filtered through a disposable frit
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting oil was dissolved in 20% solution of trifluoroacetic acid in dichloromethane (4 mL)
  4. concentrationwas concentrated in vacuo
  5. washSilica gel chromatography eluting with 2% methanol/methylene chloride

Sources & evidence

ORD record
ord-3f7ffccb23d5461487369eddd1aae6c4
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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