HCID 67174256, compound → HCID 86629724, compound

HRID 656829Notes

Reaction equation

HRID 656829 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:25](=[CH:26][C:27]=1[N+:28]([O-:30])=[O:29])[CH2:24][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]1=[O:23])[CH2:5]2.[Cl-].[C:32]([O:36][C:37](=[O:40])[CH2:38][Zn+])([CH3:35])([CH3:34])[CH3:33]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)C=CC=CC=1.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[Fe+2]>[N+:28]([C:27]1[CH:26]=[C:25]2[C:4]([CH2:5][C@:6]3([CH2:24]2)[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:7]3=[O:23])=[CH:3][C:2]=1[CH2:38][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:40])([O-:30])=[O:29]

Participants

5

Reactant 2

HCID 67174256HCID 67174256, compoundHCID 178451183HCID 178451183, compound

Product 1

HCID 86629724HCID 86629724, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzeneCatalyst

Conditions

Temperature
40 °C

Procedure

To a flask containing (2R)-5-iodo-6-nitro-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step B (4.02 g, 7.48 mmol), tris(dibenzylideneacetone)dipalladium (349 mg, 0.38 mmol), and 1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene (532 mg, 0.75 mmol) was added 2-tert-butoxy-2-oxoethylzinc chloride (Rieke, 0.5 M in Et2O; 15.7 mL, 7.85 mmol) and the resulting solution was heated to 40° C. for 1 h. The reaction was quenched with dilute aqueous NaHCO3 (100 mL) and the mixture was extracted with EtOAc (200 mL). The organic layer was washed with brine, dried over Na2 SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound, which was of sufficient purity for use in the next step. MS: m/z=526 (M+1).

Workup

  1. customThe reaction was quenched with dilute aqueous NaHCO3 (100 mL)
  2. extractionthe mixture was extracted with EtOAc (200 mL)
  3. washThe organic layer was washed with brine
  4. customdried over Na2 SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-73d7739dfdbc42539466e0c9e5fd0f7c
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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