Hydrochloric Acid → 1-(1,1,1-Trifluoro-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 624659Notes

Reaction equation

HRID 624659 reaction equation
[OH-:1].[K+].[F:3][C:4]([F:20])([F:19])[C:5]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]#N)=[CH:9]1)([CH3:7])[CH3:6].Cl.C1COCC1.C[OH:28].O>>[F:3][C:4]([F:20])([F:19])[C:5]([N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]([OH:28])=[O:1])=[CH:9]1)([CH3:7])[CH3:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 21892291Methanol tetrahydrofuran waterHCID 900331721-(1,1,1-Trifluoro-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

Product 1

HCID 900315221-(1,1,1-Trifluoro-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

Conditions

Temperature
100 °C

Procedure

KOH (174 mg, 3.11 mmol) was added to a solution of 1-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile (78.7 mg, 0.311 mmol) in 1:1:1 THF/MeOH/water (621 μl) at RT. After being stirred at 100° C. for 4 h, the reaction mixture was acidified (pH=2-3) by conc. HCl and the resulting suspension was extracted with EtOAc. The combined organic layers were concentrated to afford the title compound as a brown foam, which was used without further purification.

Workup

  1. extractionthe resulting suspension was extracted with EtOAc
  2. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-91e0cb486b604a54824766f39024a778
Source dataset
uspto-grants-2016_04
Patent number
US09303045B2

Reaction notes

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