1,4-Dioxane → HCID 86723964, compound

HRID 2209305Notes

Reaction equation

HRID 2209305 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[CH:9][N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:4]=2[CH:3]=1.[Br-:19].[Br-:20].[Br-].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.[O:40]1CCOCC1>>[Br:19][C:8]1([Br:20])[C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:10]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:9]1=[O:40]

Participants

4

Reactant 3

HCID 312751,4-Dioxane2×HCID 21124087PyridiniumtribromideHCID 86723962HCID 86723962, compound

Product 1

HCID 86723964HCID 86723964, compound

Procedure

6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-c]pyridine (1.53 g, 5.4 mmol) was added as a solution in 1,4-dioxane (10 mL) to a mixture of pyridinium tribromide (8.7 g, 27 mmol) in 1,4-dioxane (10 mL) over 30 min. Following complete addition, the reaction mixture was stirred 2 h and was then quenched with water (25 mL). The resulting mixture was stirred 20 min and was then diluted with EtOAc. The aqueous phase was extracted with EtOAc (2×) and the combined organics were washed with water (2×) and brine (2×), dried over Na2SO4, filtered, and concentrated to afford crude 3,3-dibromo-6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[3,2-c]pyridin-2(3H)-one that was used without further purification. LCMS-ESI+ (m/z): [M+H]+ calcd for C13H18Br2ClN2O2Si: 454.92; found: 454.48.

Workup

  1. additionaddition
  2. customwas then quenched with water (25 mL)
  3. stirringThe resulting mixture was stirred 20 min
  4. additionwas then diluted with EtOAc
  5. extractionThe aqueous phase was extracted with EtOAc (2×)
  6. washthe combined organics were washed with water (2×) and brine (2×)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-40a55fe45b2947e4aaf027a168ba5821
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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