Lithium Hydroxide → 4-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1923706Notes

Reaction equation

HRID 1923706 reaction equation
[Li+].[OH-].[Cl:3][C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][N:7]=[C:6]2[N:14](S(C3C=CC=CC=3)(=O)=O)[CH:15]=[CH:16][C:5]=12.S([O-])(O)(=O)=O.[K+]>C1COCC1>[Cl:3][C:4]1[C:9]([C:10]([F:12])([F:13])[F:11])=[CH:8][N:7]=[C:6]2[NH:14][CH:15]=[CH:16][C:5]=12

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 516920Potassium bisulfateHCID 509893661-(Benzenesulfonyl)-4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 509893714-Chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridineYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2M LiOH (19.1 mL, 38.2 mmol) was added to a solution of 4-chloro-1-(phenylsulfonyl)-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (4.59 g, 12.7 mmol) in THF (20 mL), and the reaction was stirred at room temperature for 20 hours. The mixture was neutralized to a pH of about 8 with saturated potassium hydrogen sulfate and extracted with ethyl acetate (50 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to provide 4-chloro-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (2.5 g, 91% yield) as a solid. 1H NMR (400 MHz, (CD3)2SO) δ 12.54 (br s, 1H), 8.59 (s, 1H), 7.82 (d, 1H), 6.71 (d, 1H); LCMS (APCI+) m/z 220.9 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1aca2eb9c765496494ed2489f7b8390e
Source dataset
uspto-grants-2012_05
Patent number
US08178131B2

Reaction notes

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