HCID 66620365, compound → HCID 66619936, compound

HRID 538596Notes

Reaction equation

HRID 538596 reaction equation
[C:1]1([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[CH2:11][C:10]([CH2:15][O:16][C:17]2[C:18]([F:27])=[C:19]([C:23]([F:26])=[CH:24][CH:25]=2)[C:20]([NH2:22])=[O:21])=[CH:9]3)[CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:6]2[CH:7]=[C:8]3[C:12](=[CH:13][CH:14]=2)[CH2:11][C:10]([CH2:15][O:16][C:17]2[C:18]([F:27])=[C:19]([C:23]([F:26])=[CH:24][CH:25]=2)[C:20]([NH2:22])=[O:21])=[CH:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 66620365HCID 66620365, compound

Product 1

HCID 66619936HCID 66619936, compoundYield 13.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 3-(5-Cyclopent-1-enyl-1H-inden-2-ylmethoxy)-2,6-difluoro-benzamide (0.05 g, 0.10 mmol) in 5 ml of anhydrous methanol was added Pd—C (10%, 100 mg). The reaction mixture was stirred at 25° C. for 48 h under hydrogen atmosphere. The reaction mixture was filtered over the bed of celite and evaporated to dryness under reduced pressure to give the title compound as white solid (0.005 g, 10%). 1H NMR (DMSO-d6, 400 MHz); δ 1.22 (m, 2H), 1.67 (m, 4H), 1.80 (m, 2H), 2.07 (m, 2H), 3.20 (m, 1H), 5.67 (s, 2H), 7.09 (m, 1H), 7.37 (m, 2H), 7.87 (m, 2H), 8.0 (m, 1H) and 8.18 (br s, 1H). MS ES+ (389.12), HPLC (method II) Rt=18.19 min.

Workup

  1. filtrationThe reaction mixture was filtered over the bed of celite
  2. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7a0893a0c67142d0b933bca8a9761ecf
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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