Cesium carbonate → HCID 178479984、化合物

HRID 1774620ノート

反応式

HRID 1774620 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([OH:8])[CH:5]=[CH:4][CH:3]=1.Br[C:10]1[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=[C:14]([Br:16])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].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>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].CN(C=O)C>[Br:16][C:14]1[CH:15]=[C:10]([NH:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]([OH:8])[N:7]=2)[C:11](=[O:18])[N:12]([CH3:17])[CH:13]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 1785076342-Amino-6-hydroxypyridine

生成物 1

HCID 178479984HCID 178479984、化合物収率 20%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A 100 mL round-bottomed flask equipped with a reflux condenser was charged with 6-aminopyridin-2-ol (1.1 g, 10.0 mmol), 3,5-dibromo-1-methylpyridin-2(1H)-one (2.67 g, 10.0 mmol), cesium carbonate (6.52 g, 20.0 mmol), xantphos (576 mg, 1.0 mmol), Pd2(dba)3 (460 mg, 0.50 mmol), and DMF (35 mL). The system was subject to three cycles of vacuum/argon flush and heated at 100° C. for 3 h. It was then cooled to room temperature and filtered. The filtrate was diluted with DCM (500 mL) and washed with H2O (80 mL×3). The organic layer was dried and concentrated under reduced pressure. The residue solid was purified by silica-gel column-chromatography eluting with DCM/MeOH (30:1 to 15:1) to afford 101a (580 mg, 20%) as yellow solid. MS-ESI: [M+H]+ 296.0

後処理

  1. customA 100 mL round-bottomed flask equipped with a reflux condenser
  2. customflush
  3. temperatureIt was then cooled to room temperature
  4. filtrationfiltered
  5. additionThe filtrate was diluted with DCM (500 mL)
  6. washwashed with H2O (80 mL×3)
  7. customThe organic layer was dried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue solid was purified by silica-gel column-chromatography
  10. washeluting with DCM/MeOH (30:1 to 15:1)

出典と根拠

ORDレコード
ord-ba545948223b408782a738b6b3c43d1b
出典データセット
uspto-grants-2016_02
特許番号
US09260415B2

反応ノート

読み込み中…