Dichloromethane → Methyl 5-bromoindoline-7-carboxylate

HRID 387244Notes

Reaction equation

HRID 387244 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]2.ClCCl.[OH-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 497588561-Tert-butyl 7-methyl 5-bromoindoline-1,7-dicarboxylate

Product 1

HCID 49758858Methyl 5-bromoindoline-7-carboxylateYield 101.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

1-(1,1-dimethylethyl) 7-methyl 5-bromo-2,3-dihydro-1H-indole-1,7-dicarboxylate (9 g, 25 mmol) was dissolved in trifluoroacetic acid (6 mL) and stirred at room temperature for 16 hours. Dichloromethane and sodium hydroxide solution (2 M) were added and the organic layer washed twice with sodium hydroxide solution until the aqueous layer pH>7. The organic layer was then concentrated in vacuo to give 6.5 g (100%) of the title compound as a brown solid.

Workup

  1. washthe organic layer washed twice with sodium hydroxide solution until the aqueous layer pH>7
  2. concentrationThe organic layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-5c40a508bb024e18afe4c58b76281c2c
Source dataset
uspto-grants-2013_02
Patent number
US08372875B2

Reaction notes

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