Lithium Chloride → HCID 66750081, compound

HRID 2174729Notes

Reaction equation

HRID 2174729 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[O:11][C:10](I)=[N:9][C:8]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1.[Cl-].[Li+].C[Sn](C)(C)[C:24]1[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=1>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.[Cu]I>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[O:11][C:10]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][CH:25]=3)=[N:9][C:8]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 433294Lithium ChlorideHCID 11128458Pyridine, 4-(trimethylstannyl)-HCID 66749702HCID 66749702, compound

Product 1

HCID 66750081HCID 66750081, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Ethyl 5-(4-chlorobenzyl)-2-iodo-1,3-oxazole-4-carboxylate (261 mg, 0.666 mmol), Tetrakis(triphenylphosphine)palladium(0) (38.5 mg, 0.0333 mmol), Copper(I) iodide (38.1 mg, 0.200 mmol) and Lithium chloride (84.8 mg, 2.00 mmol) under atmosphere of argon was dissolved in 1,4-Dioxane (18 mL) and Trimethyl(4-pyridyl)tin (207 uL, 1.20 mmol) was added. The mixture was heated at 100° C. for 2 h. The mixture was evaporated and the residue was purified by chromatography to afford Ethyl 5-(4-chlorobenzyl)-2-pyridin-4-yl-1,3-oxazole-4-carboxylate (0.133 g, 58.2%). LCMS (FA) ES+ 343.2, 345.1

Workup

  1. customThe mixture was evaporated
  2. customthe residue was purified by chromatography

Sources & evidence

ORD record
ord-cbe5390d22fa4e41b9bcfe68916b5e85
Source dataset
uspto-grants-2015_06
Patent number
US09062038B2

Reaction notes

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