HCID 69658884, compound → HCID 69658351, compound

HRID 2212968Notes

Reaction equation

HRID 2212968 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH2:9][CH2:8][C@@H:7]1[C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[N:21])[CH:18]=2)[NH:13][CH:12]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 69658884HCID 69658884, compound

Product 1

HCID 69658351HCID 69658351, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(5-Cyano-1H-indol-3-yl)-cyclopent-1-enecarboxylic acid ethyl ester (1.20 g, 4.3 mMol) was stirred and heated slightly until dissolved in methanol (250 mL). 10% palladium on carbon (300 mg) was added and the reaction was shaken in a Parr apparatus under hydrogen (50 psi) for 1 h. The reaction was filtered through Celite and sand, and the solvent was evaporated in vacuo. The product was obtained as a white solid (1.08 g, 89%). 1H NMR (400 MHz, CDCl3) δ 8.31 (1H, bs), 8.00 (1H, s), 7.37 (2H, AB, δv=18 Hz, J=8.4 Hz), 7.09 (1H, d, J=1.5 Hz), 3.63 (2H, m), 3.48 (1H, m), 3.28 (1H, q, J=6.5 Hz), 2.00–2.22 (5H, m), 1.76 (1H, m), 0.63 (3H, t, J=6.8 Hz); MS m/e 305.2 (M+Na).

Workup

  1. temperatureheated slightly
  2. filtrationThe reaction was filtered through Celite and sand
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-627ca2dfc1d640cfb72bd1c31f001f90
Source dataset
uspto-grants-2006_09
Patent number
US07105516B2

Reaction notes

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