HCID 68423194, compound → HCID 59317143, compound

HRID 1805209Notes

Reaction equation

HRID 1805209 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:15][C:16]([CH:19]=[CH:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)=[C:12]([CH3:24])[C:11]([C:25]2[N:26]([CH3:33])[C:27]([CH3:32])([CH3:31])[C:28](=[O:30])[N:29]=2)=[N:10]1>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:14]2[S:15][C:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:17][CH:18]=2)=[C:12]([CH3:24])[C:11]([C:25]2[N:26]([CH3:33])[C:27]([CH3:32])([CH3:31])[C:28](=[O:30])[N:29]=2)=[N:10]1

Participants

4

Reactant 1

HCID 68423194HCID 68423194, compound

Product 1

HCID 59317143HCID 59317143, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 43 (118 mg, 0.24 mmol) and Pd—C (12 mg) in MeOH (8 mL) was stirred under 1 atm of H2 at room temperature for 2 h. The reaction mixture was filtered and the resulting filtrate was concentrated under reduced pressure to give the crude residue, which was subjected to purification by flash chromatography on silica gel with hexanes/ethyl acetate (1:1) to afford the product 44 (75 mg, 62%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.48 (d, 1H), 7.29 (m, 2H), 6.77 (d, 1H), 6.61 (d, 1H), 3.57 (s, 3H), 2.65 (m, 5H), 1.60 (m, 8H), 1.22 (m, 4H), 0.81 (t, 3H); ESMS m/z: 503.0 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe resulting filtrate was concentrated under reduced pressure
  3. customto give the crude residue, which
  4. customwas subjected to purification by flash chromatography on silica gel with hexanes/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-987066f2f1504fbbbe0788334125555e
Source dataset
uspto-grants-2013_01
Patent number
US08354442B2

Reaction notes

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