Cesium carbonate → N-ethyl-N'-(6-fluoro-3,4'-bipyridin-2'-yl)urea

HRID 2243059ノート

反応式

HRID 2243059 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([NH:11][CH2:12][CH3:13])=[O:10])[CH:3]=1.[F:14][C:15]1[CH:20]=[CH:19][C:18](B2OC(C)(C)C(C)(C)O2)=[CH:17][N:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[CH2:12]([NH:11][C:9]([NH:8][C:4]1[CH:3]=[C:2]([C:18]2[CH:17]=[N:16][C:15]([F:14])=[CH:20][CH:19]=2)[CH:7]=[CH:6][N:5]=1)=[O:10])[CH3:13]

参加物

4

反応物 3

HCID 10796Cesium carbonateHCID 121772222-Fluoropyridine-5-boronic acid pinacol esterHCID 592083771-(4-Bromopyridin-2-yl)-3-ethylurea2 回

生成物 1

HCID 59208411N-ethyl-N'-(6-fluoro-3,4'-bipyridin-2'-yl)urea収率 84.3%

実験手順

N-(4-bromopyridin-2-yl)-N′-ethylurea (Intermediate 33, 0.40 g, 1.64 mmol), 2-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.057 g, 4.92 mmol), tetrakis triphenyl phosphine palladium (0.189 g, 0.16 mmol), and cesium carbonate (1.16 g, 4.92 mmol) were taken in a microwave vial and degassed with nitrogen. A dioxane:water (4:1, 10 mL) solution was added to the vial and the mixture was microwaved at 110° C. for half an hour. The palladium was filtered off, and the reaction was partitioned between water and ethyl acetate. The layers were separated, and the organic layer was washed with saturated sodium bicarbonate solution, water and brine, then dried over magnesium sulfate, and concentrated. The residue obtained was washed with acetonitrile to give the title compound as a white solid (360 mg).

後処理

  1. customdegassed with nitrogen
  2. additionA dioxane:water (4:1, 10 mL) solution was added to the vial and the mixture
  3. customwas microwaved at 110° C. for half an hour
  4. filtrationThe palladium was filtered off
  5. customthe reaction was partitioned between water and ethyl acetate
  6. customThe layers were separated
  7. washthe organic layer was washed with saturated sodium bicarbonate solution, water and brine
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated
  10. customThe residue obtained
  11. washwas washed with acetonitrile

出典と根拠

ORDレコード
ord-b8dfce097e2b42d2be4023ab6a3bd21c
出典データセット
uspto-grants-2010_03
特許番号
US07674801B2

反応ノート

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