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Cesium carbonate → Ethyl 5-(5-formylfuran-2-yl)nicotinate

HRID 1645265
Notes
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Reaction equation

HRID 1645265 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:19]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])O1.Br[C:22]1[O:26][C:25]([CH:27]=[O:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:27]([C:25]1[O:26][C:22]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:19]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:23][CH:24]=1)=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 3816953Ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate

Product 1

HCID 59190169Ethyl 5-(5-formylfuran-2-yl)nicotinateYield 100.2%

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (570 mg, 2.06 mmol), 5-bromofuran-2-carbaldehyde (300 mg, 1.71 mmol), Cs2CO3 (1.125 g, 3.46 mmol) and PdCl2(dppf) (65 mg, 0.09 mmol) in H2O/dioxane (5%, 10 mL) was heated at reflux for 15 min. The reaction mixture was cooled to rt and diluted with H2O (100 mL). The resulting precipitate was collected by filtration to yield the desired ethyl 5-(5-formylfuran-2-yl)nicotinate (420 mg). LCMS (ES): m/z 246 [M+1]+.

Workup

  1. temperatureat reflux for 15 min
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f59a0ff580b74294aa6c0754a5bc9847
Source dataset
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08124649B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes