Dichloromethane → Methyl 2 inverted exclamation mark-Oxo-1 inverted exclamation mark-[[2-(trimethylsilyl)ethoxy]methyl]-1 inverted exclamation mark,2 inverted exclamation mark,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3 inverted exclamation mark-pyrrolo[2,3-b]pyridine]-3-carboxylate

HRID 588723Notes

Reaction equation

HRID 588723 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:27][C:9]3([C:17]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:10]3=[O:26])[CH2:8][C:5]2=[N:6][CH:7]=1.[CH2:28](Cl)Cl.[C:31]([O-:34])(=[O:33])C.[Na+].[C]=O>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[O:26]=[C:10]1[N:11]([CH2:18][O:19][CH2:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[C:9]21[CH2:8][C:5]1=[N:6][CH:7]=[C:2]([C:31]([O:34][CH3:28])=[O:33])[CH:3]=[C:4]1[CH2:27]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 68749705HCID 68749705, compound2×HCID 178418416HCID 178418416, compound

Product 1

HCID 131734435Methyl 2 inverted exclamation mark-Oxo-1 inverted exclamation mark-[[2-(trimethylsilyl)ethoxy]methyl]-1 inverted exclamation mark,2 inverted exclamation mark,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3 inverted exclamation mark-pyrrolo[2,3-b]pyridine]-3-carboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 887MethanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-bromo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (described in Intermediate 2) (22.0 g, 49.3 mmol), PdCl2(dppf).CH2Cl2 (2.012 g, 2.46 mmol), and sodium acetate (8.1 g, 99 mmol) in MeOH (150 mL) was pressurized to 300 psi of carbon monoxide and then heated at 85° C. for 72 h. The reaction mixture was allowed to cool then concentrated in vacuo. The residue was purified by silica gel chromatography, eluting with a gradient of heptane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=426.1 (M+1).

Workup

  1. temperatureto cool
  2. concentrationthen concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with a gradient of heptane

Sources & evidence

ORD record
ord-fbfd66fc901344bab79d4f21f480d7a7
Source dataset
uspto-grants-2016_01
Patent number
US09227972B2

Reaction notes

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