Methanol → Methyl (2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylate

HRID 340158Notes

Reaction equation

HRID 340158 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[CH2:16][C@:6]1([C:14]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[NH:8][C:7]1=[O:15])[CH2:5]2.[C:20]([O-:23])(=[O:22])C.[Na+].[CH3:25]O>C1(C)C=CC=CC=1.O.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].C(Cl)Cl>[O:15]=[C:7]1[NH:8][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:14]2[C@:6]21[CH2:5][C:4]1[C:17](=[CH:18][CH:19]=[C:2]([C:20]([O:23][CH3:25])=[O:22])[CH:3]=1)[CH2:16]2

Participants

7

Reactant 3

HCID 887MethanolHCID 517045Sodium AcetateHCID 58118662(2R)-5-iodo-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Product 1

HCID 86695345Methyl (2R)-2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-carboxylate

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (2R)-5-iodo-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (100.0 g, 276 mmol), sodium acetate (45.3 g, 552 mmol) and Pd(dppf)Cl2—CH2Cl2 (11.3 g, 13.8 mmol) in a mixture of MeOH (1 L) and toluene (30 mL) was pressurized to 120 psi of CO at 23° C. and then heated at 80° C. for 12 h with stirring. The reaction mixture was diluted with water (1 L), and the precipitate collected by filtration, washed with water, and dried under nitrogen atmosphere to give the title compound, which was used without further purification. MS: m/z=295.3 (M+1).

Workup

  1. customwas pressurized to 120 psi of CO at 23° C.
  2. filtrationthe precipitate collected by filtration
  3. washwashed with water
  4. customdried under nitrogen atmosphere

Sources & evidence

ORD record
ord-79372ebc255546d59b2affe65a04fc39
Source dataset
uspto-grants-2014_11
Patent number
US08895572B2

Reaction notes

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