Methanol → HCID 90050656, compound

HRID 931377Notes

Reaction equation

HRID 931377 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:18][C:8]3([C:16]4[C:11](=[N:12][CH:13]=[CH:14][CH:15]=4)[NH:10][C:9]3=[O:17])[C:7](=[O:19])[C:6]=2[CH:20]=1.[C:21]([O-:24])(=[O:23])C.[Na+].[C]=O.[CH3:28]O>O.ClCCl.[Pd+2].ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[O:17]=[C:9]1[NH:10][C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]21[C:7](=[O:19])[C:6]1[CH:20]=[C:2]([C:21]([O:24][CH3:28])=[O:23])[CH:3]=[CH:4][C:5]=1[O:18]2

Participants

7

Reactant 4

HCID 887MethanolHCID 517045Sodium AcetateHCID 58458896HCID 58458896, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 90050656HCID 90050656, compound

Reagents, catalysts & solvents 2

HCID 178478475HCID 178478475, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 5-bromo-3H-spiro[1-benzofuran-2,3′-pyrrolo[2,3-b]pyridine]-2′,3(1′H)-dione (300 mg, 0.91 mmol), sodium acetate (149 mg, 1.81 mmol) and dichloro 1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloromethane adduct (18 mg, 0.023 mmol) in MeOH (5 mL) is pressurized to 120 psi with carbon monoxide and then heated at 80° C. for 12 h with stirring. The reaction mixture is diluted with water (20 mL), and the precipitate collected by filtration, washed with water, and dried under nitrogen atmosphere to give the title compound.

Workup

  1. filtrationthe precipitate collected by filtration
  2. washwashed with water
  3. customdried under nitrogen atmosphere

Sources & evidence

ORD record
ord-22162a5b4bd84f748b7c56d8c3bee803
Source dataset
uspto-grants-2016_03
Patent number
US09296750B2

Reaction notes

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