Dichloromethane → 2-(3,3-Difluoro-2-oxoindolin-1-yl)acetic acid

HRID 1519847Notes

Reaction equation

HRID 1519847 reaction equation
[F:1][C:2]1([F:20])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[C:3]1=[O:19].C(Cl)Cl>C(O)=O>[F:20][C:2]1([F:1])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][C:12]([OH:14])=[O:13])[C:3]1=[O:19]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 68754561tert-Butyl 2-(3,3-difluoro-2-oxoindolin-1-yl)acetate

Product 1

HCID 687551942-(3,3-Difluoro-2-oxoindolin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A 30 mL reaction vial was charged with tert-butyl 2-(3,3-difluoro-2-oxoindolin-1-yl)acetate (275 mg, 1 mmol) as a yellow oil. DCM (3 mL) was added, followed by an equal volume of formic acid. The reaction was stirred for 16 h. The reaction mixture was concentrated under reduced pressure to give 2-(3,3-difluoro-2-oxoindolin-1-yl)acetic acid as a yellow solid. The desired M+H (228) was observed in the LCMS using the method [1] with a retention time of 1.652 min.

Workup

  1. customA 30 mL reaction
  2. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dd22639bc42e46c08963effbada514bd
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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