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Cesium carbonate → Tert-butyl (4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamate

HRID 626569
Notes
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Reaction equation

HRID 626569 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:18])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[C:19](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH2:20].C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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.[Fe+2].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]>[CH3:18][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:19](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:7]=2)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

Product 1

HCID 131735225Tert-butyl (4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamateYield 29.1%

Reagents, catalysts & solvents 3

HCID 635956
Ferrocene-1,1'-bis-(diphenylphosphine)
Catalyst
HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Example A3 (1.2 g, 4.52 mmol), t-butyl carbamate (1.058 g, 9.03 mmol), Cs2CO3 (2.94 g, 9.03 mmol) and DPPF (0.351 g, 0.632 mmol) in dioxane (25 mL) was sparged with Ar, treated with Pd2(dba)3 (0.290 g, 0.316 mmol), sparged again with Ar and heated at 100° C. for 3 days. The mixture was cooled to RT, diluted with EtOAc, the solids removed via filtration through diatomaceous earth and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford tert-butyl (4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)carbamate (456 mg, 29%). MS (ESI) m/z: 347.2 (M+H+).

Workup

  1. customsparged again with Ar
  2. temperatureThe mixture was cooled to RT
  3. additiondiluted with EtOAc
  4. customthe solids removed via filtration through diatomaceous earth
  5. concentrationthe filtrate concentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-383f2caff4064bbbb9f6c7fb2fb266c8
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309224B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes