2-(Tributylstannyl)pyridine → Tert-butyl-3-(pyridin-2-yl)benzylcarbamate

HRID 513293

Reaction equation

HRID 513293 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](I)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([Sn](CCCC)(CCCC)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=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>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 11645663tert-Butyl 3-iodobenzylcarbamate

Product 1

HCID 69029928Tert-butyl-3-(pyridin-2-yl)benzylcarbamateYield 78.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl-3-iodobenzylcarbamate (166 mg, 0.50 mmol) in Dioxane (1.5 mL) was added Pd(PPh3)4 (58 mg, 0.05 mmol) and 2-(tributylstannyl)pyridine (275 mg, 0.75 mmol). After stirring at 100° C. for 2 h, it was concentrated and the residue was purified by column chromatography to give tert-butyl-3-(pyridin-2-yl)benzylcarbamate (111 mg).

Workup

  1. concentrationit was concentrated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e72f51f70e1d4e489c74252f62880107
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Linked notes

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