Sodium Hydroxide → 4-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1187282Notes

Reaction equation

HRID 1187282 reaction equation
C([N:5]1[C:9]2=[N:10][CH:11]=[CH:12][C:13]([C:14]([F:17])([F:16])[F:15])=[C:8]2[C:7](C#N)=[CH:6]1)(C)(C)C.[OH-].[Na+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O>[F:16][C:14]([F:15])([F:17])[C:13]1[CH:12]=[CH:11][N:10]=[C:9]2[NH:5][CH:6]=[CH:7][C:8]=12

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 455883331-tert-Butyl-4-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 235151154-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridineYield 50%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
120 °C

Procedure

1-tert-Butyl-4-trifluoromethyl-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (25, 1.071 g, 4.007 mmol) is dissolved in 10 mL of aqueous 60% sulfuric acid and stirred at 120° C. for 20 hours. The reaction is adjusted to pH ˜7 with sodium hydroxide and aqueous saturated sodium bicarbonate, then extracted with ethyl acetate. The organic layer is washed with water, then brine and dried with magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with ethyl acetate and hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (26, 373 mg). MS (ESI) [M+H+]+=187.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialbrine and dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe resulting material is purified by silica gel column chromatography
  7. washeluting with ethyl acetate and hexane
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f15cf2b1a33445febdad509ab11cf864
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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