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2-(Tributylstannyl)pyridine → [1-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

HRID 2036657
Notes
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Reaction equation

HRID 2036657 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1I)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)CCC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH:11]([C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[N:17][N:16]2[C:21]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 67433097[1-(3-Iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 67431406[1-(3-Pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
110 °C

Procedure

To a solution of [1-(3-iodo-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester (3.0 g, 7.1 mmol) and 2-tributylstannanyl-pyridine (7.8 g, 21.32 mmol) in 1,4-dioxane (20 mL) was added Pd(PPh3)4 (820 mg, 0.71 mmol) at rt. The reaction mixture was stirred overnight at 110° C. After completion of the reaction, the mixture was concentrated in vacuo. The crude product was purified by column chromatography using silica gel (100-200 mesh) and 0-40% acetone in hexane to provide [1-(3-pyridin-2-yl-imidazo[1,2-b]pyridazin-2-yl)-ethyl]-carbamic acid benzyl ester: LC-MS (ESI) m/z 374.1 [M+H]+.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-f503bbfd05344e7da689ff5562e83f9c
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08575183B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes