HCID 58269171, compound → HCID 58269245, compound

HRID 239641Notes

Reaction equation

HRID 239641 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C:7]([CH2:12][N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[C:6]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:5]2=[O:25].[H][H]>CO.[Pd]>[O:16]1[CH2:17][CH2:18][N:13]([CH2:12][C:7]2[O:8][C:9]3[C:4]([C:5](=[O:25])[C:6]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:3][CH:2]=[CH:11][CH:10]=3)[CH2:14][CH2:15]1

Participants

5

Reactant 2

HCID 58269171HCID 58269171, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58269245HCID 58269245, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 2 (0.1 g, 0.249 mmoles) in methanol (10 ml), palladium on carbon 20 mg) was added and the solution was hydrogenated at RT under 5 kg/cm2 pressure of hydrogen for 4 h. The solution was filtered through celite and concentrated. The crude product was purified by column chromatography with ethyl acetate: petroleum ether to afford the title compound as brown solid (0.080 g, 87% yield).: 1H-NMR (δ ppm, DMSO-D6, 400 MHz): δ 8.08(d, J=7.8 Hz, 1H), 7.90(t, J=7.4 Hz, 1H), 7.74 (d, J=8.4 Hz, 1H), 7.55(t, J=7.4 Hz, 1H), 7.49(m, 3H), 7.31(d, J=6.5 Hz, 2H), 3.72(br s,4H), 3.42(br s, 6H).

Workup

  1. filtrationThe solution was filtered through celite
  2. concentrationconcentrated
  3. customThe crude product was purified by column chromatography with ethyl acetate

Sources & evidence

ORD record
ord-3d58d4caa22d426cb69ebe9258a31d07
Source dataset
uspto-grants-2014_02
Patent number
US08642607B2

Reaction notes

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