HCID 54526935, compound → HCID 22928381, compound

HRID 751463Notes

Reaction equation

HRID 751463 reaction equation
[CH2:1]([N:4]([CH2:14][C:15]([CH3:20])([CH3:19])[CH2:16][CH:17]=[CH2:18])[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)(=[O:7])=[O:6])C=C>C(Cl)Cl.Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl>[CH3:20][C:15]1([CH3:19])[CH2:16][CH:17]=[CH:18][CH2:1][N:4]([S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)(=[O:6])=[O:7])[CH2:14]1

Participants

4

Reactant 1

HCID 54526935HCID 54526935, compound

Product 1

HCID 22928381HCID 22928381, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Pyridine-2-sulfonic acid allyl-(2,2-dimethyl-pent-4-enyl)-amide (0.6 g, 2 mmol) was diluted in CH2Cl2 (50 ml) After carefully degass by Ar, Grubbs catalyst (0.17 g, 0.2 mmol) was added under Ar protection. The mixture was then refluxed for 2 h before the solvent was removed on rotavapor. The crude product was purified by column chromatography (5%-20% E/H) to give 0.47 g of the title compound in 87% yield. MS (M+H+): 267.0; 1H-NMR (400 MHz, CDCl3): •8.70-8.69(d, 1H), 7.96-7.88(m, 2H), 7.49-7.46(m, 1H), 5.81-5.70(m, 2H), 3.93-3.92(d, 2H), 3.26(s, 2H), 2.13-2.12(d, 2H), 1.00(s, 6H)

Workup

  1. additionwas added under Ar protection
  2. temperatureThe mixture was then refluxed for 2 h before the solvent
  3. customwas removed on rotavapor
  4. customThe crude product was purified by column chromatography (5%-20% E/H)

Sources & evidence

ORD record
ord-2eda30b9c9654577ae45a76ead2d51d5
Source dataset
uspto-grants-2008_07
Patent number
US07405209B2

Reaction notes

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