Trifluoroacetic acid → Ethyl 5-bromoindoline-7-carboxylate

HRID 656002Notes

Reaction equation

HRID 656002 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[N:9]1(C(OC(C)(C)C)=O)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:11][CH2:10]1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl>[Br:8][C:14]1[CH:13]=[C:12]2[C:17](=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=1)[NH:9][CH2:10][CH2:11]2

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 593325671-(1,1-Dimethylethyl) 7-ethyl 2,3-dihydro-1H-indole-1,7-dicarboxylate

Product 1

HCID 59332604Ethyl 5-bromoindoline-7-carboxylateYield 164.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

NBS (51.3 g, 0.29 mol) was added in several portions to a solution of 1-(1,1-dimethylethyl) 7-ethyl 2,3-dihydro-1H-indole-1,7-dicarboxylate (140.3 g, 0.48 mol) in CH2Cl2 (1200 mL) and the reaction mixture was stirred at room temperature overnight. The reaction solution was washed with 2 M NaOH (500 mL) and water (500 mL), and was then dried (Na2SO4). The solution was concentrated in vacuo to 500 mL and TFA (130 mL, 1.69 mol) was added. The mixture was stirred at room temperature overnight. A solution of 2 M NaOH was added to bring the reaction mixture to pH>8. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3×300 mL). The combined organic layers were dried (Na2SO4) and the solvent was evaporated, giving 129.1 g (99%) of the title compound.

Workup

  1. washThe reaction solution was washed with 2 M NaOH (500 mL) and water (500 mL)
  2. dry with materialwas then dried (Na2SO4)
  3. additionwas added
  4. stirringThe mixture was stirred at room temperature overnight
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with CH2Cl2 (3×300 mL)
  7. dry with materialThe combined organic layers were dried (Na2SO4)
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7915d15a226148a9b3637dcc01179326
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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