HCID 86703272, compound → HCID 86703273, compound

HRID 2409948Notes

Reaction equation

HRID 2409948 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([CH2:21][C:22]3[N:27]=[C:26]([C:28]([O:30]CC4C=CC=CC=4)=[O:29])[CH:25]=[CH:24][CH:23]=3)=[C:11]2[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([CH2:21][C:22]3[N:27]=[C:26]([C:28]([OH:30])=[O:29])[CH:25]=[CH:24][CH:23]=3)=[C:11]2[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86703272HCID 86703272, compound

Product 1

HCID 86703273HCID 86703273, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 6-(1-benzenesulfonyl-6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (1.10 g) in ethyl acetate (9.3 mL) was added 10% palladium on carbon (56.5% water included, 253 mg), and this mixture was stirred at room temperature for 100 minutes under a hydrogen atmosphere. The reaction mixture was filtrated through a Celite (registered trademark) pad. The filtrate was concentrated under reduced pressure to obtain the title compound (869 mg). 1H-NMR (DMSO-d6) δ ppm: 3.84 (3H, s), 3.97 (2H, s), 6.87 (1H, dd, J=2.3, 8.6 Hz), 6.95-7.02 (1H, m), 7.30 (1H, d, J=8.6 Hz), 7.40-7.51 (7H, m), 7.56-7.68 (4H, m), 7.70-7.85 (2H, m), 12.80-13.60 (1H, br).

Workup

  1. filtrationThe reaction mixture was filtrated through a Celite (registered trademark) pad
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cfc9021c89dd4e9f9ec8d9bde13d0b84
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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