Benzyl Alcohol → HCID 67778295, compound

HRID 1026293Notes

Reaction equation

HRID 1026293 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[N:6][CH:7]=1.[CH2:22]([OH:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.C1(C)C=CC=CC=1>[CH2:22]([O:29][C:2]1[CH:3]=[N:4][C:5]([C:8]2[O:9][C:10]3[CH:16]=[C:15]([O:17][CH2:18][CH:19]4[CH2:21][CH2:20]4)[CH:14]=[CH:13][C:11]=3[N:12]=2)=[N:6][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 67778974HCID 67778974, compound

Product 1

HCID 67778295HCID 67778295, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Under an argon atmosphere, a mixture of 2-(5-bromopyrimidin-2-yl)-6-(cyclopropylmethoxy)-1,3-benzoxazole (260 mg), benzyl alcohol (812 mg), cesium carbonate (368 mg), copper(I) iodide (14.3 mg), 1,10-phenanthroline (27.0 mg) and toluene (5 mL) was stirred at 110° C. for 3 days. The precipitate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a pale-yellow solid (205 mg).

Workup

  1. customThe precipitate was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-b2455680d9444329953b2f68d1321646
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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