HCID 86723964, compound → HCID 86723963, compound

HRID 1475347Notes

Reaction equation

HRID 1475347 reaction equation
Br[C:2]1(Br)[C:6]2[CH:7]=[N:8][C:9]([Cl:11])=[CH:10][C:5]=2[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:3]1=[O:20]>C1COCC1.[Cl-].[NH4+].[Zn]>[Cl:11][C:9]1[N:8]=[CH:7][C:6]2[CH2:2][C:3](=[O:20])[N:4]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:18])([CH3:17])[CH3:19])[C:5]=2[CH:10]=1

Participants

5

Reactant 1

HCID 86723964HCID 86723964, compound

Product 1

HCID 86723963HCID 86723963, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Zinc powder (14.8 g, 226 mmol) was added to a biphasic mixture of 3,3-dibromo-6-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one (10.3 g, 22.6 mmol) in THF (129 mL) and saturated ammonium chloride solution (33 mL). Due to delayed exotherm, the reaction was cooled in ice. The reaction was stirred for 3 h at ambient temperature, filtered and the filtrate concentrated. The residue was dissolved in EtOAc (20 mL) and water (20 mL) and passed through a short plug of celite, washing with EtOAc. The organic layer was separated and the aqueous phase extracted with EtOAc (2×20 mL). The combined organic solutions were washed with brine, dried over magnesium sulfate, filtered and concentrated. Chromatography on silica gel (gradient elution, 0-100%, EtOAc/petrol), gave the title compound (5.08 g, 75%) as a pale yellow oil. 1H NMR (Me-d3-OD): 8.14 (1H, s), 7.18 (1H, s), 5.17 (2H, s), 3.63 (2H, t), 0.94 (2H, t), 0.18-0.18 (9H, m).

Workup

  1. temperaturethe reaction was cooled in ice
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated
  4. dissolutionThe residue was dissolved in EtOAc (20 mL)
  5. washwashing with EtOAc
  6. customThe organic layer was separated
  7. extractionthe aqueous phase extracted with EtOAc (2×20 mL)
  8. washThe combined organic solutions were washed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-60cf8bf8862747d78c45132e96e2c91c
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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