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Cesium carbonate → 1,1-Dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea

HRID 626521
Notes
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Reaction equation

HRID 626521 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.[CH3:19][N:20]([CH3:24])[C:21]([NH2:23])=[O:22].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([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[CH3:19][N:20]([CH3:24])[C:21]([NH:23][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)=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11737N,N-DimethylureaHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 904036213-((2-Chloropyridin-4-yl)oxy)-2-methyl-6-nitropyridine

Product 1

HCID 904098671,1-Dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)ureaYield 86%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of Example A3 (0.500 g, 1.882 mmol) in dioxane (10 mL) was sparged with Ar, treated with N,N-dimethylurea (0.829 g, 9.41 mmol), XANTPHOS (218 mg, 0.376 mmol), and Cs2CO3 (1.226 g, 3.76 mmol), sparged with Ar, treated with Pd2(dba)3 (0.172 g, 0.188 mmol), sparged again with Ar and heated at 100° C. overnight. The mixture was cooled to RT and diluted with EtOAc. The solids were removed via filtration through diatomaceous earth and washed with EtOAc. The filtrates were concentrated to dryness and purified via silica gel chromatography (MeOH/EtOAc) to afford 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea (511 mg, 86%). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.25-8.19 (m, 2H), 7.82 (d, J=8.7 Hz, 1H), 7.50 (d, J=2.3 Hz, 1H), 6.71 (dd, J=5.7, 2.4 Hz, 1H), 2.89 (s, 6H), 2.73 (s, 3H); MS (ESI) m/z: 318.1 (M+H+).

Workup

  1. customsparged with Ar
  2. customsparged again with Ar
  3. temperatureThe mixture was cooled to RT
  4. additiondiluted with EtOAc
  5. customThe solids were removed via filtration through diatomaceous earth
  6. washwashed with EtOAc
  7. concentrationThe filtrates were concentrated to dryness
  8. custompurified via silica gel chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-4e2e563dfe204e9ea28940588b325941
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