Tetrahydrofuran → HCID 66865449, compound

HRID 252531Notes

Reaction equation

HRID 252531 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](OC)[CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1)#[N:2].[OH-].[Na+].C1C[O:31][CH2:30]C1>O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([O:31][CH3:30])=[CH:9][CH:10]=2)[N:5]([CH2:14][CH3:15])[C:4]=1[C:16]1[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)#[N:2]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59426315HCID 59426315, compound

Product 1

HCID 66865449HCID 66865449, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

Methyl 4-(3-cyano-1-ethyl-5-methoxy-1H-indol-2-yl)-benzoate (350 mg, 1.05 mmol), prepared as described in Example 1Ga step B, is combined with NaOH (40 mg, 1 mmol), H2O (0.8 mL), and THF (3.4 mL) and is heated at 80° C. for 1 hour. The reaction mixture is diluted in H2O and is then ether-washed. The aqueous layer is acidified with aqueous HCl, and is extracted into EtOAc. The organic layer is dried and concentrated to yield 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-benzoic acid (311 mg, 92%) as a pure white solid.

Workup

  1. washether-washed
  2. extractionis extracted into EtOAc
  3. customThe organic layer is dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6303c2e190264e4eaf1c072ed18a9d5d
Source dataset
uspto-grants-2011_01
Patent number
US07868037B2

Reaction notes

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