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HRID626523

反应详情

EQUATION

反应方程式

HRID 626523 的结构方程式

REACTANTS

反应物

4
结构：O=C([O-])[O-].[Cs+].[Cs+]
HCID10796

Cesium carbonate

CCs2O3

结构：CN(C)C(N)=O
HCID11737

1,1-Dimethylurea

C3H8N2O

结构：CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21
HCID636044

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C39H32OP2

结构：Cc1nc([N+](=O)[O-])ccc1Oc1ccnc(Cl)c1
HCID90403621

未命名化合物

PRODUCTS

生成物

1
结构：Cc1nc([N+](=O)[O-])ccc1Oc1ccnc(NC(=O)N(C)C)c1
HCID90409867

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

2
结构：O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.[Pd].[Pd]
催化剂HCID9811564

Bis(dibenzylideneacetone)palladium

C51H42O3Pd2

结构：C1COCCO1
溶剂HCID31275

1,4-Dioxane

C4H8O2

CONDITIONS

反应条件

温度
100 °C

PROCEDURE

实验过程

A solution of Example A3 (8.0 g, 30 mmol) in dioxane (150 mL) was sparged with Ar under sonication for 20 min, treated with N,N-dimethylurea (10.6 g, 120 mmol), XANTPHOS (3.48 g, 6.02 mmol), and Cs2CO3 (1.226 g, 3.76 mmol), sparged with Ar under sonication for 30 min, treated with Pd2(dba)3 (2.76 g, 3.01 mmol), sparged again with Ar under sonication for 30 min 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. The residue was partitioned into EtOAc and water. The aqueous layer was back-extracted with EtOAc (3×) and the combined organics were dried (Na2SO4) and concentrated. MeCN was added and the mixture was sonicated. The solids were collected by filtration to provide 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea, crop 1. The filtrate was concentrated to dryness. Fresh MeCN was added and the mixture was again sonicated. The solids were collected by filtration to provide 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea, crop 2. The filtrate was concentrated in vacuo 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, crop 3. Crops 1-3 of 1,1-dimethyl-3-(4-((2-methyl-6-nitropyridin-3-yl)oxy)pyridin-2-yl)urea were combined (5.2 g, 54%). MS (ESI) m/z: 288.1 (M+H+).

WORKUP

后处理

  1. customsparged with Ar under sonication for 30 min
  2. customsparged again with Ar under sonication for 30 min
  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. customThe residue was partitioned into EtOAc and water
  9. extractionThe aqueous layer was back-extracted with EtOAc (3×)
  10. dry with materialthe combined organics were dried (Na2SO4)
  11. concentrationconcentrated
  12. additionMeCN was added
  13. customthe mixture was sonicated
  14. filtrationThe solids were collected by filtration