HCID 59430527, compound → HCID 59425469, compound

HRID 252560Notes

Reaction equation

HRID 252560 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) is stirred in 20% TFA in CH2Cl2 at room temperature for 3 hours. This is concentrated and the residue is partitioned between H2O and EtOAc. The organic layer is dried and concentrated. The residue is 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 is concentrated
  2. customthe residue is partitioned between H2O and EtOAc
  3. customThe organic layer is dried
  4. concentrationconcentrated
  5. customThe residue is triturated with CH2Cl2

Sources & evidence

ORD record
ord-84e4beb9067148b38becce1e9dfdc2aa
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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