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

HRID 57978
Notes
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Reaction equation

HRID 57978 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.CCN(C(C)C)C(C)C.[CH3:20][Si:21]([CH2:24][CH2:25][O:26][CH2:27]Cl)([CH3:23])[CH3:22]>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH2:27][O:26][CH2:25][CH2:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a solution of 6-chloro-1H-pyrazolo[4,3-c]pyridine (2.00 g, 13.1 mmol) and DIPEA (3 mL) in DCM (10 mL) was added SEMCl (3 mL). The mixture was stirred at 30° C. for 20 hours. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography using EtOAc/Petroleum Ether (10%˜60%) as eluting solvents to afford 6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[4,3-c]pyridine as colorless oil (3.44 g, 93%). MS (ESI) m/z: 284 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography
  3. washas eluting solvents

Sources & evidence

ORD record
ord-068c61179eb841218dd995ff96c532a2
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434725B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes