Trifluoroacetic acid → 2,2-Difluoro-2-(3-methoxyquinolin-6-yl)acetic acid

HRID 2176639Notes

Reaction equation

HRID 2176639 reaction equation
[F:1][C:2]([F:22])([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH3:21])=[CH:13]2)[C:3]([O:5]C(C)(C)C)=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[F:22][C:2]([F:1])([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][C:14]([O:20][CH3:21])=[CH:13]2)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57691317HCID 57691317, compound

Product 1

HCID 576912392,2-Difluoro-2-(3-methoxyquinolin-6-yl)acetic acidYield 101.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 200 mL round bottom flask was charged with tert-butyl 2,2-difluoro-2-(3-methoxyquinolin-6-yl)acetate (5.06 g, 16 mmol) then CH2Cl2, then trifluoroacetic acid (16 ml, 213 mmol) followed by triethylsilane (6.5 ml, 41 mmol). The solution was maintained at rt for 24 h until LCMS showed disappearance of starting material. The solution was concentrated and was subjected to high vacuum for 40 h to give 4.1 g (99% yield) of 2,2-difluoro-2-(3-methoxyquinolin-6-yl)acetic acid as a brown solid. The material was of sufficient purity for use in subsequent steps.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-85d6245fd2004c2b8228d29c32ceccd7
Source dataset
uspto-grants-2015_06
Patent number
US09066954B2

Reaction notes

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