Cesium carbonate → 5-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one

HRID 2069765ノート

反応式

HRID 2069765 の反応式
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[CH:7]=1.[CH3:11][N:12]1[CH:16]=[CH:15][C:14]([NH2:17])=[N:13]1.C1(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O.C1(C)C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:17][C:14]2[CH:15]=[CH:16][N:12]([CH3:11])[N:13]=2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 1372541-Methyl-3-aminopyrazoleHCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 10993848Diphenylphosphino-1,1'-binaphthyl

生成物 1

HCID 592164605-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)pyridin-2(1H)-one収率 54.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

3,5-Dibromo-1-methyl-1H-pyridin-2-one (469 mg, 1.76 mmol), 1-Methyl-1H-pyrazol-3-ylamine (205 mg, 2.11 mmol), tris(dibenzylidineacetone)dipalladium(0) (80 mg, 0.087 mmol), 2,2′-bis(diphenylphosphino-1,1′-binaphthalene (82 mg, 0.13 mmol), and cesium carbonate (801 mg, 2.46 mmol) were deposited in a sealed vial with 10 mL toluene. This was heated at 130° C. for 18 hours. The resulting mixture was poured into 50 mL water. This was extracted with ethylacetate. The ethylacetate layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, concentrated in vacuo, and purified by flash chromatography (eluted with ethylacete/hexanes) to yield 5-Bromo-1-methyl-3-(1-methyl-1H-pyrazol-3-ylamino)-1H-pyridin-2-one (271 mg, 0.957 mmol). MS (ESI) 284.9 (M+H)+.

後処理

  1. extractionThis was extracted with ethylacetate
  2. washThe ethylacetate layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (eluted with ethylacete/hexanes)

出典と根拠

ORDレコード
ord-08d49ac8e1e64402b42454af39a367e2
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

読み込み中…