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Cesium carbonate → 3-(5-Bromopyridin-3-yl)oxazolidin-2-one

HRID 712761
Notes
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Reaction equation

HRID 712761 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6](I)[CH:7]=1.[O:9]1[CH2:13][C:12](=O)[N:11]=[C-:10]1.C1(P(C2C=CC=CC=2)C2C3[O:34]C4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([N:11]2[CH2:12][CH2:13][O:9][C:10]2=[O:34])[CH:5]=[N:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 8204093-Bromo-5-iodopyridineHCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 679825123-(5-Bromopyridin-3-yl)oxazolidin-2-oneYield 232.9%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

An argon purged flask (100 mL) is charged with reagent 3-bromo-5-iodopyridine (200 mg, 0.704 mmol), 2-oxazolidone (61.3 mg, 0.704 mmol), tris(dibenzylideneacetone)dipalladium(0) (64.5 mg, 0.07 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (61.1 mg, 0.106 mmol), and cesium carbonate (459 mg, 1.409 mmol). Toluene (bubbled with argon before use, 14 mL) is then added. The resulting mixture is heated at 90° C. under argon for 16 h. The mixture is filtered through diatomaceous earth and washed with MeOH (30 mL). The filtrate is concentrated. The resulting crude product is purified by normal phase chromatography using 0-4.5% MeOH in DCM as the gradient to afford 3-(5-bromo-pyridin-3-yl)-oxazolidin-2-one (60 mg, 35% yield).

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth
  2. washwashed with MeOH (30 mL)
  3. concentrationThe filtrate is concentrated
  4. customThe resulting crude product is purified by normal phase chromatography

Sources & evidence

ORD record
ord-a74c260997024399b59abd22c9e732e5
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181272B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes