HCID 58052458, compound → HCID 58052525, compound

HRID 2190180Notes

Reaction equation

HRID 2190180 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:28][C:11]3=[N:12][C:13]([N:18]([CH2:23][CH2:24][CH2:25]C=C)[S:19]([CH3:22])(=[O:21])=[O:20])=[C:14]([CH:16]=[CH2:17])[CH:15]=[C:10]3[C:9]=2[C:29]([NH:31][CH3:32])=[O:30])=[CH:4][CH:3]=1>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C(Cl)Cl>[CH3:32][NH:31][C:29]([C:9]1[C:10]2[CH:15]=[C:14]3[CH:16]=[CH:17][CH2:25][CH2:24][CH2:23][N:18]([S:19]([CH3:22])(=[O:21])=[O:20])[C:13]3=[N:12][C:11]=2[O:28][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:30]

Participants

4

Reactant 1

HCID 58052458HCID 58052458, compound

Product 1

HCID 58052525HCID 58052525, compound

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-(4-fluorophenyl)-N-methyl-6-(N-(pent-4-enyl)methylsulfonamido)-5-vinylfuro[2,3-b]pyridine-3-carboxamide (5.0 mg, 1 eq.), Hoveyda-Grubbs catalyst 2nd generation (0.7 mg, 0.1 eq.) and methylene chloride (0.55 ml) was degassed and stirred in a microwave reactor at 100° C. for 15 min. The reaction mixture was diluted with EtOAc, filtered through a 0.2 μM PTFE syringe filter and concentrated to yield the crude title compound which was used without purification in the next step.

Workup

  1. customwas degassed
  2. additionThe reaction mixture was diluted with EtOAc
  3. filtrationfiltered through a 0.2 μM PTFE syringe
  4. filtrationfilter
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fb39f7e19d25486096120dae882af0a8
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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