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Ethyl 1H-indole-3-acetate → tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate

HRID 1471628
Notes
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Reaction equation

HRID 1471628 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.[Br:16]N1C(=O)CCC1=O.[C:24]([O:31]C(OC(C)(C)C)=O)(=O)[O:25][C:26]([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Br:16][C:2]1[N:1]([C:24]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:31])[C:9]2[C:4]([C:3]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:6]=[CH:7][CH:8]=2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13067Ethyl 1H-indole-3-acetateHCID 67184N-bromobutanimideHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonate

Product 1

HCID 90281421tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylateYield 67.1%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ethyl 2-(1H-indol-3-yl)acetate (5 g, 24.6 mmol) in 25 ml of DCM was added N-bromosuccinimide (4.38 g, 24.6 mmol) in small portions at 0° C. The mixture was warmed to room temperature and stirred for 6 hours. Di-tert-butyl pyrocarbonate (10.74 g, 49.2 mmol), DIPEA (8.6 ml, 49.5 mmol) and DMAP (cat) was added to the mixture. The reaction was stirred overnight. The mixture was diluted with DCM (100 ml) and washed with HCl (0.5 N, 2×50 ml). The organic layer was dried with Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography on silica (5-20 EtOAc/hexanes) to get 6.3 g (16.5 mmol) of product. MS (m/z) 382 [M+H]+.

Workup

  1. stirringThe reaction was stirred overnight
  2. washwashed with HCl (0.5 N, 2×50 ml)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was introduced to a silica gel loading column
  7. custompurified by column chromatography on silica (5-20 EtOAc/hexanes)

Sources & evidence

ORD record
ord-1e14f1328bbf4979b2146d42f154a45f
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012441B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes