Potassium Carbonate → 3-[(2-Bromo-5-chloro-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl]benzonitrile

HRID 628420Notes

Reaction equation

HRID 628420 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][C:6]([Cl:11])=[CH:7][CH:8]=2)[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:18]([C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br)#[N:19]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[N:10]([CH2:23][C:22]2[CH:21]=[C:20]([CH:27]=[CH:26][CH:25]=2)[C:18]#[N:19])[C:9]2[C:4](=[N:5][C:6]([Cl:11])=[CH:7][CH:8]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 1181597982-bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine

Product 1

HCID 1181594783-[(2-Bromo-5-chloro-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl]benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-5-chloro-1H-pyrrolo[3,2-b]pyridine (2.0 g, 8.6 mmol, prepared as in Example 103, Step 1) in DMF (20. mL) was treated with K2CO3 (1.8 g, 13 mmol) and m-cyanobenzyl bromide (1.9 g, 9.5 mmol, Aldrich) overnight. The reaction mixture was diluted with EtOAc and washed sequentially with water and brine. The combined organic extracts were dried over sodium sulfate, filtered and concentrated. The solid obtained was triturated with hexanes/diethyl ether and isolated by filtration. Yield: (2.3 g, 77%).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe solid obtained
  6. customwas triturated with hexanes/diethyl ether
  7. customisolated by filtration

Sources & evidence

ORD record
ord-1f51672eefb24ea19ce3456e6f81ea2f
Source dataset
uspto-grants-2016_04
Patent number
US09309246B2

Reaction notes

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