Diisopropylethylamine → 2-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane

HRID 57825Notes

Reaction equation

HRID 57825 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][NH:10][C:4]=2[CH:3]=1.C(N(CC)C(C)C)(C)C.[CH3:20][Si:21]([CH3:28])([CH3:27])[CH2:22][CH2:23][O:24][CH2:25]Cl>ClCCl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH2:25][O:24][CH2:23][CH2:22][Si:21]([CH3:28])([CH3:27])[CH3:20])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 569321096-Chloro-1H-pyrazolo(4,3-c)pyridine

Product 1

HCID 867070302-[(6-Chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silaneYield 16.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-chloro-1H-pyrazolo[4,3-c]pyridine (12.82 mmol; 1968 mg) in Dichloromethane (50 mL) was added N,N-Diisopropylethylamine (38.45 mmol, 6.7 mL). 2-(Trimethylsilyl)ethoxymethyl chloride (19.22 mmol; 3205 mg; 3.40 mL) was then added dropwise at room temperature. The resulting mixture was stirred overnight. The mixture was partitioned between DCM and water. The organic layer was concentrated and the residue was purified on silica eluted with 0 to 6% MeOH in DCM to afford 2-[(6-chloropyrazolo[4,3-c]pyridin-1-yl)methoxy]ethyl-trimethyl-silane (590 mg, 13%).

Workup

  1. customThe mixture was partitioned between DCM and water
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified on silica
  4. washeluted with 0 to 6% MeOH in DCM

Sources & evidence

ORD record
ord-265545f7134544fabbc95a4932c47b6e
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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