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1,10-Phenanthroline → 2-(5-Bromopyridin-3-yl)-1,3-benzoxazole

HRID 2041801
Notes
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Reaction equation

HRID 2041801 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:17]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1Br)=[O:8].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(OCC)(=O)C>O1CCOCC1.[Cu]I>[Br:1][C:2]1[CH:17]=[C:6]([C:7]2[O:8][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=2)[CH:5]=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1019799HCID 1019799, compound

Product 1

HCID 252394772-(5-Bromopyridin-3-yl)-1,3-benzoxazoleYield 75%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

A mixture of 5-bromo-N-(2-bromophenyl)nicotinamide (4) (3.44 g, 9.7 mmol), CuI (0.106 g, 0.56 mmol), Cs2CO3 (3.91 g, 12 mmol) and 1,10-phenathroline (0.20 g, 1.12 mmol) in anhydrous 1,4-dioxane (50 mL) was heated at 100° C. overnight. After cooled cooling to RT, the mixture was poured into ethyl acetate (200 mL), then washed with water. The aqueous phase was extracted with ethyl acetate (200 mL×2), and the organic phase was collected and dried over Na2SO4, and purified by flash chromatography (silica gel, hexanes/ethyl acetate 3:1) to give a light yellow solid (5) (2.0 g, 75% yield).

Workup

  1. temperatureAfter cooled
  2. temperaturecooling to RT
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with ethyl acetate (200 mL×2)
  5. customthe organic phase was collected
  6. dry with materialdried over Na2SO4
  7. custompurified by flash chromatography (silica gel, hexanes/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-13916050656b4cf59575b60eec6026b1
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08585926B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes