3-(5-Methoxy-1H-indol-3-yl)-acrylic acid methyl ester → Methyl 3-(5-methoxy-1H-indol-3-yl)propanoate

HRID 1394017Notes

Reaction equation

HRID 1394017 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]=[CH:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1>O1CCCC1.[Pd]>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][CH:7]=1

Participants

4

Reactant 1

HCID 588430803-(5-Methoxy-1H-indol-3-yl)-acrylic acid methyl ester

Product 1

HCID 54357260Methyl 3-(5-methoxy-1H-indol-3-yl)propanoateYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-Methoxy-1H-indol-3-yl)-acrylic acid methyl ester 3 (3 g; 0.013 mol) in tetrahydrofuran (THF, 70 mL) was added palladium on activated carbon (10%; 0.72 g ). The solution was deoxygenated under vacuum and hydrogen was introduced to the reaction flask from a balloon filled with hydrogen. The process was repeated three times and the reaction mixture was stirred for 16 h at room temperature. The mixture was filtered through celite and the filtrate was evaporated under reduced pressure to yield ester 4 as a while solid (2.78 g; 92% yield; M+1=234.0).

Workup

  1. customThe solution was deoxygenated under vacuum and hydrogen
  2. additionwas introduced to the reaction flask from a balloon
  3. additionfilled with hydrogen
  4. filtrationThe mixture was filtered through celite
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e3e7b613a74a4275a3de54160a9e257c
Source dataset
uspto-grants-2008_03
Patent number
US07348338B2

Reaction notes

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