5-Bromoindoline → tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylate

HRID 49504Notes

Reaction equation

HRID 49504 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[C:11]([O:15][C:16](OC([O-])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[C:11]([O:15][C:16]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 34115665-BromoindolineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 21865438tert-butyl 5-bromo-2,3-dihydro-1H-indole-1-carboxylateYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 g (20 mmol) 5-bromo-indoline in 50 ml CH2Cl2 were treated with 4.4 g (20 MMOL) di.-tert.-butyldicarbonate at RT over night. The reaction mixture was concentrated in vacuo and triturated with hexane to yield 5.3 g (89%) 5-Bromo-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 297 (M, 1Br).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with hexane

Sources & evidence

ORD record
ord-f7a7d38a65524aa78f0024818bae38cd
Source dataset
uspto-grants-2004_03
Patent number
US06706751B2

Reaction notes

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