2-(Tributylstannyl)pyridine → Benzyl carbamate

HRID 2036649Notes

Reaction equation

HRID 2036649 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10]C(C1N=C2C=NC=CN2C=1I)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)C1C=CC=CN=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])[NH2:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 67432906[1-(3-Iodo-imidazo[1,2-a]pyrazin-2-yl)-ethyl]-carbamic acid benzyl ester

Product 1

HCID 12136Benzyl carbamate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of [1-(3-iodo-imidazo[1,2-a]pyrazin-2-yl)-ethyl]-carbamic acid benzyl ester (1.6 g, 3.79 mmol) and 2-tributylstannanyl pyridine (4.1 g, 11.37 mmol) in 1,4-dioxane (20 mL) was added Pd(PPh3)4 (50 mg, 0.4 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-a]pyrazin-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-74f01aaee58b4abf978447d0b24c5b8b
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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