HCID 58550634, compound → HCID 59165777, compound

HRID 1685384Notes

Reaction equation

HRID 1685384 reaction equation
[CH2:1]([C:4]1([CH2:22][CH:23]=C)[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:5]1=[O:21])[CH:2]=C>Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1.ClCCCl>[CH3:20][Si:17]([CH3:18])([CH3:19])[CH2:16][CH2:15][O:14][CH2:13][N:6]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:12]2[C:4]2([CH2:1][CH:2]=[CH:23][CH2:22]2)[C:5]1=[O:21]

Participants

4

Reactant 1

HCID 58550634HCID 58550634, compound

Product 1

HCID 59165777HCID 59165777, compound

Reagents, catalysts & solvents 2

HCID 178425456HCID 178425456, compoundCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3,3-diallyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one from Step A (1.02 g, 2.96 mmol) and Grubbs second generation catalyst (37 mg, 0.045 mmol) in DCE (60 mL) was heated at reflux for 3.5 h. The mixture was concentrated in vacuo and purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 75:25, to give the title compound. MS: m/z=317 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by silica gel chromatography
  5. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-fd1c5206b86447f8801f0f17577bbca8
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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