HCID 10891349, compound → HCID 11833001, compound

HRID 1182500Notes

Reaction equation

HRID 1182500 reaction equation
[OH:1][NH:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]/[C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1>CO.[Pd]>[OH:1][NH:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=1

Participants

4

Reactant 1

HCID 10891349HCID 10891349, compound

Product 1

HCID 11833001HCID 11833001, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 179 (30 mg, 0.106 mmol) in methanol (2 mL) was added a catalytic amount of 10% palladium on charcoal. The mixture was degassed and applied under hydrogen atmosphere and stirred for 15 minutes. Hydrogen was evacuated by vacuum and the mixture was filtered through Celite and rinsed with methanol. The filtrate was concentrated in vacuo, affording the title compound 180 (29.1 mg) in 97% yield. 1H NMR: (300 MHz, CD3OD) δ: 7.80-7.74 (m, 3H), 7.60 (s, 1H), 7.44-7.37 (m, 2H), 7.33 (dd, J=8.2, 1.6 Hz, 1H), 2.77 (t, J=7.4 Hz, 2H), 2.07 (t, J=7.1 Hz, 2H), 1.71-1.64 (m, 2H), 1.62-1.57 (m, 2H), 1.37-1.28 (m, 6H). HRMS (calc.): 285.1729, (found): 285.1727.

Workup

  1. customThe mixture was degassed
  2. customHydrogen was evacuated by vacuum
  3. filtrationthe mixture was filtered through Celite
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-b72154b95f0c44d5921dd52fa6e65c66
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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