HCID 59430527, compound → HCID 59425469, compound

HRID 907168Notes

Reaction equation

HRID 907168 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH2:28][CH3:29])[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][CH:20]=[C:19]([O:26][CH3:27])[CH:18]=3)=[CH:11][CH:10]=1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[C:24]([C:23]1[C:22]2[C:17](=[CH:18][C:19]([O:26][CH3:27])=[CH:20][CH:21]=2)[N:16]([CH2:28][CH3:29])[C:15]=1[C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([OH:30])=[O:5])=[CH:10][CH:11]=1)#[N:25]

Participants

4

Reactant 1

HCID 59430527HCID 59430527, compound

Product 1

HCID 59425469HCID 59425469, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[4-(3-Cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenoxy]-acetic acid tert-butyl ester (745 mg, 1.83 mmol) was stirred in 20% TFA in CH2Cl2 at room temperature for 3 hours. This was concentrated and the residue was partitioned between H2O and EtOAc. The organic layer was dried and concentrated. The residue was triturated with CH2Cl2 to yield [4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenoxy]-acetic acid (634 mg, 99%) as a white solid.

Workup

  1. concentrationThis was concentrated
  2. customthe residue was partitioned between H2O and EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was triturated with CH2Cl2

Sources & evidence

ORD record
ord-2cd071bdad5f4141bf333c3b038f4431
Source dataset
uspto-grants-2011_09
Patent number
US08013006B2

Reaction notes

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