Sodium Methoxide → Sodium 5-(4-isopropoxyphenyl)-1-(2-naphthyl)indole-2-carboxylate

HRID 646114Notes

Reaction equation

HRID 646114 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]2[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=2)[C:15]([C:30]([OH:32])=[O:31])=[CH:14]3)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C[O-].[Na+:35]>C1COCC1>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16]([C:20]2[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=2)[C:15]([C:30]([O-:32])=[O:31])=[CH:14]3)=[CH:9][CH:10]=1)([CH3:3])[CH3:2].[Na+:35]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 686968775-(4-Isopropoxyphenyl)-1-(2-naphthyl)indole-2-carboxylic acid

Product 1

HCID 68702464Sodium 5-(4-isopropoxyphenyl)-1-(2-naphthyl)indole-2-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-(4-Isopropoxyphenyl)-1-(2-naphthyl)indole-2-carboxylic acid (40 mg, 0.095 mmol; see Example 18) was dissolved in dry THF (1 mL) and NaOMe (3.37 M, 28 μL) was added via syringe. After stirring for 30 min at room temperature, the solvents were removed under reduced pressure and the residue dried in vacuo to yield the title compound (42 mg, 99%).

Workup

  1. customthe solvents were removed under reduced pressure
  2. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-fec5dbf52c024ac3929f3149fc571cb6
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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