N-bromobutanimide → HCID 70980601, compound

HRID 1475422Notes

Reaction equation

HRID 1475422 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:20]N1C(=O)CCC1=O>CC#N>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Br:20])=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH3:19])([CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70980896HCID 70980896, compound

Product 1

HCID 70980601HCID 70980601, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 6-chloro-3,3-dimethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl-ester (0.500 g, 2.75 mmol) in MeCN (3.78 mL) was added N-bromosuccinimide (0.492 g, 2.76 mmol) at room temperature. The reaction was stirred for 1 h at room temperature and concentrated. Chromatography (silica gel, gradient elution, 0-40%, EtOAc in petrol 40-60) gave the title compound (356 mg), 1H NMR (Me-d3-OD): 7.80 (1H, s), 7.43 (1H, s), 3.73 (2H, s), 1.66-1.51 (9H, m), 1.32 (6H, s).

Workup

  1. concentrationconcentrated
  2. washChromatography (silica gel, gradient elution, 0-40%, EtOAc in petrol 40-60)

Sources & evidence

ORD record
ord-22b0e7a17cc74884aa3481a4e91cdc20
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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