Water → tert-Butyl 6-bromoindoline-1-carboxylate

HRID 1790392Notes

Reaction equation

HRID 1790392 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[Br:13][C:14]1[CH:22]=[C:21]2[C:17]([CH2:18][CH2:19][NH:20]2)=[CH:16][CH:15]=1.C(N(CC)CC)C.O>O1CCCC1.C(OCC)(=O)C>[C:8]([O:7][C:1]([N:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]([Br:13])[CH:22]=2)[CH2:18][CH2:19]1)=[O:12])([CH3:9])([CH3:10])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 130983796-Bromo-2,3-dihydro-1H-indole

Product 1

HCID 22038386tert-Butyl 6-bromoindoline-1-carboxylateYield 71.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Di-t-butyl carbonate (6.7 g) was added to a solution of 6-bromoindoline (5.1 g) and triethylamine (3.1 g) in tetrahydrofuran (50 ml) followed by stirring the resultant mixture at room temperature overnight. After adding water and ethyl acetate thereto, the layers were separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The residue was then purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (5.5 g) as a colorless oil (yield: 71%).

Workup

  1. customthe layers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe residue was then purified by silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-addcacbb6213493293811ebb667a59e9
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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