5-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester → 5-(3-Methanesulfonylamino-propyl)-thiophene-2-carboxylic Acid Methyl Ester

HRID 842743Notes

Reaction equation

HRID 842743 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]#[C:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][CH:9]=1)=[O:4]>CCOC(C)=O.CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 1

HCID 537526885-(3-Methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 536710815-(3-Methanesulfonylamino-propyl)-thiophene-2-carboxylic Acid Methyl EsterYield 97.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-(3-methanesulfonylamino-prop-1-ynyl)-thiophene-2-carboxylic acid methyl ester (3.0 g, 10.9 mmol) in EtOAc (100 mL) and MeOH (50 mL) was hydrogenated with 10% palladium on carbon (680 mg) at 50 psi for 7 h. The solution was filtered through a pad of Celite® with the aid of MeOH and was concentrated in vacuo to provide the title compound as an off-white solid (2.95 g). 1H NMR (300 MHz, CDCl3) δ 7.62 (d, 1H), 7.23 (d, 1H), 4.29 (m, 1H), 3.85 (s, 3H), 3.18 (q, 2H), 2.93 (m, 5H), 1.96 (m, 2H).

Workup

  1. filtrationThe solution was filtered through a pad of Celite® with the aid of MeOH
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-399219b7d90b4d3d86a69f863c8b86ba
Source dataset
uspto-grants-2002_04
Patent number
US06376502B1

Reaction notes

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