Sodium hydride → 7-Bromo-3-(4-chlorophenoxy)-2-methyl-4-nitro-1H-indole-1-acetic acid 1,1 dimethylethyl ester

HRID 2233742Notes

Reaction equation

HRID 2233742 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N+:22]([O-:24])=[O:23])=[C:8]2[C:12]=1[NH:11][C:10]([CH3:13])=[C:9]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1.[C:25]([O:29][C:30](=[O:33])[CH2:31]Br)([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[CH3:26][C:25]([O:29][C:30](=[O:33])[CH2:31][N:11]1[C:12]2[C:8](=[C:7]([N+:22]([O-:24])=[O:23])[CH:6]=[CH:5][C:4]=2[Br:3])[C:9]([O:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[C:10]1[CH3:13])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 686177447-Bromo-3-(4-chlorophenoxy)-2-methyl-4-nitro-1H-indole

Product 1

HCID 686169457-Bromo-3-(4-chlorophenoxy)-2-methyl-4-nitro-1H-indole-1-acetic acid 1,1 dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% disp. in oil) (0.043 g) was added to a stirred solution of the product from step (ii) (0.34 g) in THF (4 ml) at RT. After 1 h, tert-butylbromoacetate (170 ul) was added, the mixture stirred at RT for 16 h then quenched with water and extracted with diethylether. The organics were dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 10% diethylether/iso-hexane. Yield 0.192 g

Workup

  1. customthen quenched with water
  2. extractionextracted with diethylether
  3. customThe organics were dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica eluting with 10% diethylether/iso-hexane

Sources & evidence

ORD record
ord-c29fd276727a4aaf9275bf1ca0a241b4
Source dataset
uspto-grants-2010_05
Patent number
US07709521B2

Reaction notes

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