Water → 3-bromo-5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

HRID 1960052Notes

Reaction equation

HRID 1960052 reaction equation
[CH:1]1([CH2:6][N:7]([C:10]2[N:15]=[C:14]3[CH:16]=[CH:17][N:18]([CH3:19])[C:13]3=[CH:12][C:11]=2[C:20]#[N:21])[CH2:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:22]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:22][C:16]1[C:14]2=[N:15][C:10]([N:7]([CH2:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH2:8][CH3:9])=[C:11]([C:20]#[N:21])[CH:12]=[C:13]2[N:18]([CH3:19])[CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 578612815-[N-(cyclopentylmethyl)-N-ethylamino]-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Product 1

HCID 578612643-bromo-5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (105 mg, 0.37 mmol) in DMF (2 mL) is added N-bromosuccinimide (NBS, 66 mg, 0.37 mmol) at 0° C. After stirring for 30 min, H2O is added, and the reaction mixture is extracted with EtOAc. The organic layer is dried over sodium sulfate, concentrated and purified by silica-gel column chromatography to give 3-bromo-5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile as a yellow solid.

Workup

  1. extractionthe reaction mixture is extracted with EtOAc
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. concentrationconcentrated
  4. custompurified by silica-gel column chromatography

Sources & evidence

ORD record
ord-b1dc272d11cd4a81a39c59137662c139
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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