Water → HCID 118161807, compound

HRID 2203658Notes

Reaction equation

HRID 2203658 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[NH:10][N:9]=[CH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].Cl[CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH3:15].O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[N:10]([CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH3:15])[N:9]=[CH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 126752472-(1-Chloroethyl)pyridineHCID 401522596-Bromo-1H-pyrazolo[4,3-b]pyridine

Product 1

HCID 118161807HCID 118161807, compoundYield 49.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27 °C

Procedure

To an ice-cooled solution of 6-bromo-1H-pyrazolo[4,3-b]pyridine (0.60 g, 3.0 mmol) in N,N-dimethylformamide (30 mL) was added sodium hydride (60%, 488 mg, 12.2 mmol). After 30 min, 2-(1-chloroethyl)pyridine (1.73 g, 12.2 mmol) was added to reaction mixture, and the resulting suspension was warmed to 27° C. After 17 h, the reaction mixture was poured into water (50 mL), and the resulting solution was extracted with ethyl acetate (3×30 mL). The organic extracts were concentrated in vacuo. Purification by flash column chromatography (6→15% ethyl acetate in petroleum ether) afforded 6-bromo-1-(1-(pyridin-2-yl)ethyl)-1H-pyrazolo[4,3-b]pyridine (450 mg, 49% yield). LRMS (ESI): [MH]+=304.6.

Workup

  1. waitAfter 17 h
  2. extractionthe resulting solution was extracted with ethyl acetate (3×30 mL)
  3. concentrationThe organic extracts were concentrated in vacuo
  4. customPurification by flash column chromatography (6→15% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-91876389d0c947bca9e9887f9e658dd9
Source dataset
uspto-grants-2016_06
Patent number
US09365583B2

Reaction notes

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