Proton sponge → HCID 67155995, compound

HRID 2196715Notes

Reaction equation

HRID 2196715 reaction equation
CN(C)C1C2C(=CC=CC=2N(C)C)C=CC=1.F[B-](F)(F)F.[CH3:22][O+:23]([CH3:25])C.[N+:26]([C:29]1[CH:30]=[C:31]2[CH:37]=[C:36](CO)[N:35]([S:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)(=[O:42])=[O:41])[C:32]2=[N:33][CH:34]=1)([O-:28])=[O:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:22][O:23][CH2:25][C:36]1[N:35]([S:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)(=[O:41])=[O:42])[C:32]2=[N:33][CH:34]=[C:29]([N+:26]([O-:28])=[O:27])[CH:30]=[C:31]2[CH:37]=1

Participants

6

Reactant 4

HCID 88675Proton spongeHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 67155969HCID 67155969, compound

Product 1

HCID 67155995HCID 67155995, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N,N′,N′-Tetramethyl-1,8-naphthalenediamine (0.212 g, 0.99 mmol) and trimethyloxonium tetrafluoroborate (0.146 g, 0.99 mmol) were added to a solution of (5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)methanol (0.11 g, 0.33 mmol) in DCM (3.3 mL). The reaction mixture was stirred at room temperature for 1 hour. It was then treated with saturated aqueous NaHCO3, and the layers were separated. The aqueous layer was extracted with DCM. The combined organic layers were dried with sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography to afford 2-(methoxymethyl)-5-nitro-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.11 g, 96%).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with DCM
  3. dry with materialThe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-f0f2ad8ffba84b188ea713751a483c4b
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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