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Trifluoroacetic acid → 1-(1-cyclopropyl-1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

HRID 2206598
Notes
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Reaction equation

HRID 2206598 reaction equation
[CH:1]1([CH:4]([O:24][CH3:25])[CH:5]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9]([C:16]([O:18]C(C)(C)C)=[O:17])=[C:8]2[CH3:23])[CH3:6])[CH2:3][CH2:2]1.C(C(O)=O)(F)(F)F>C(Cl)Cl>[CH:1]1([CH:4]([O:24][CH3:25])[CH:5]([N:7]2[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:10]3[C:9]([C:16]([OH:18])=[O:17])=[C:8]2[CH3:23])[CH3:6])[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89740019HCID 89740019, compound

Product 1

HCID 1177786371-(1-cyclopropyl-1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of tert-butyl 1-(1-cyclopropyl-1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylate (100 mg, 0.29 mmol) in CH2Cl2 (2 mL) were added CF3CO2H (2 mL). The solution was stirred at 25° C. for 2 h. After the reaction completed, the solution was concentrated under reduced pressure to obtain 1-(1-cyclopropyl-1-methoxypropan-2-yl)-2-methyl-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid as red oil. (87 mg, yield 99%).

Workup

  1. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-90c2005c6c144e75a9d04ea1eb50bc39
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371331B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes