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Tetrahydrofuran → Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoate

HRID 2069058
Notes
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Reaction equation

HRID 2069058 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1.C([NH:19][C:20](=[O:22])[O-:21])(C)(C)C.[C:23](=O)([O-])[O-].[Cs+].[Cs+].[CH2:29]1[CH2:33]OC[CH2:30]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[C:29]([O:21][C:20]([NH:19][C:2]1[CH:7]=[C:6]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][N:3]=1)=[O:22])([CH3:30])([CH3:33])[CH3:23]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 21252905Tert-butylcarbamateHCID 58532560Ethyl 2-(2-chloropyridin-4-yl)propanoate

Product 1

HCID 58532575Ethyl 2-(2-(tert-butoxycarbonylamino)pyridin-4-yl)propanoateYield 61%

Reagents, catalysts & solvents 2

HCID 636044
1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 2-(2-chloropyridin-4-yl)propanoate (51) (1.55 g, 7.25 mmol), tert-butylcarbamate (2.55 g, 21.76 mmol), Pd2 dba3 (0.166 g, 0.181 mmol), caesium carbonate (3.55 g, 10.88 mmol) and Xantphos (0.210 g, 0.363 mmol) in THF (10 mL) was purged with nitrogen and heated at 65° C. for 48 hr. The mixture was then cooled to RT, diluted with water and extracted with ether. The ether layer was washed with water and brine and then dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution) to afford the title compound (52) (1.35 g, 61%): m/z 295 (M+H)+ (ES+).

Workup

  1. customwas purged with nitrogen
  2. temperatureThe mixture was then cooled to RT
  3. additiondiluted with water
  4. extractionextracted with ether
  5. washThe ether layer was washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (SiO2, 100 g, 5-10% EtOAc in isohexane, gradient elution)

Sources & evidence

ORD record
ord-663ab8ce6d8147fdbdd8d3baf21496f6
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08299073B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes