N-bromobutanimide → HCID 131735833, compound

HRID 2206108Notes

Reaction equation

HRID 2206108 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[CH:11][C:7]=2[C:6]([C:20]#[N:21])=[CH:5][N:4]=1.C1C(=O)N([Br:29])C(=O)C1>C(OCC)(=O)C>[Br:29][C:11]1[C:7]2[C:6]([C:20]#[N:21])=[CH:5][N:4]=[C:3]([O:2][CH3:1])[C:8]=2[N:9]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:17])([CH3:19])[CH3:18])[CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 131735831HCID 131735831, compound

Product 1

HCID 131735833HCID 131735833, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 7-methoxy-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (1.34 g) in ethyl acetate (20.15 mL) was added NBS (1.97 g) at room temperature, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.30 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3d4826117f774ea5aa9535597dddc705
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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