Ammonium Chloride → HCID 86723963, compound

HRID 2209306Notes

Reaction equation

HRID 2209306 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].[NH4+].[Cl-]>C1COCC1.[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 2

HCID 25517Ammonium ChlorideHCID 86723964HCID 86723964, compound

Product 1

HCID 86723963HCID 86723963, compoundYield 64.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Crude 3,3-dibromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (˜5.4 mmol) was taken up in a mixture of THF (30 mL) and saturated aqueous NH4Cl (8 mL). Zinc powder (3.6 g, 0.055 mmol) was added, and a modest exotherm was maintained via ice bath. The reaction was stirred at r.t. for 1.5 h, and the reaction was then filtered through Celite, washing with EtOAc. The organic phase was washed with water, and the combined aqueous phase was extracted with EtOAc. The combined organics were dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography (10-100% EtOAc in hexanes) to afford 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (1.04 g). LCMS-ESI+ (m/z): [M+H]+ calcd for C13H20ClN2O2Si: 299.10; found: 298.98.

Workup

  1. temperaturea modest exotherm was maintained via ice bath
  2. filtrationthe reaction was then filtered through Celite
  3. washwashing with EtOAc
  4. washThe organic phase was washed with water
  5. extractionthe combined aqueous phase was extracted with EtOAc
  6. dry with materialThe combined organics were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a crude residue that
  10. customwas purified by silica gel chromatography (10-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c8caa5ae3abf4aa5a12b6be6f17ee31e
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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