3-[1-(4-Methoxy benzenesulfonyl)-5-methoxy-1H-indol-3-yl]-acrylic acid → Indeglitazar

HRID 384867Notes

Reaction equation

HRID 384867 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH:23]=[CH:24][C:25]([OH:27])=[O:26])=[CH:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1>C1COCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[CH:13]2)(=[O:10])=[O:11])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 684848023-[1-(4-Methoxy benzenesulfonyl)-5-methoxy-1H-indol-3-yl]-acrylic acid

Product 1

HCID 11395145Indeglitazar

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-(4-Methoxy benzenesulfonyl)-5-methoxy-1H-indol-3-yl]-acrylic acid 118 (1.0 g, 2.6 mmol) dissolved in THF (14 mL), Pd/C (67 mg) was added in one portion. The solution was attached to the Parr hydrogenator. The reaction was allowed to proceed overnight at 20-22 psi. The solution was filtered over celite, and the palladium-celite pad was washed with ethyl acetate (40 mL), and methanol (20 mL). The combined washes/solution was evaporated under reduced pressure to afford straw colored oil that solidified after cooling under high vacuum. The crude was triturated with diethyl ether to leave behind off white solid as product 1. (0.620 g, 62%) 1H NMR (DMSO) δ 7.86 (d, J=9.2 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 6.92 (dd, J=2.4 Hz, 9.2 Hz, 1H), 6.88 (s, 1H), 6.83 (d, J=9.2 Hz, 2H), 3.76 (s, 3H), 2.96 (t, J=7.6 Hz, 14.8 Hz, 2H), 2.74 (t, J=7.6 Hz, 14.8 Hz, 2H) (M−1=388.6).

Workup

  1. filtrationThe solution was filtered over celite
  2. washthe palladium-celite pad was washed with ethyl acetate (40 mL), and methanol (20 mL)
  3. customThe combined washes/solution was evaporated under reduced pressure
  4. customto afford straw colored oil that solidified
  5. temperatureafter cooling under high vacuum
  6. customThe crude was triturated with diethyl ether
  7. customto leave behind off white solid as product 1

Sources & evidence

ORD record
ord-ea447c3dc7e649858f7e1c8997babc03
Source dataset
uspto-grants-2013_02
Patent number
US08367828B2

Reaction notes

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