Potassium Phosphate, Tribasic → 5'-Methoxy-5-morpholino-2,3'-bipyridin-3-amine

HRID 1431583ノート

反応式

HRID 1431583 の反応式
Cl[C:2]1[C:7]([NH2:8])=[CH:6][C:5]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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].O.O1CCOCC1>[CH3:15][O:16][C:17]1[CH:18]=[C:19]([C:2]2[C:7]([NH2:8])=[CH:6][C:5]([N:9]3[CH2:14][CH2:13][O:12][CH2:11][CH2:10]3)=[CH:4][N:3]=2)[CH:20]=[N:21][CH:22]=1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27630875-Methoxypyridine-3-boronic AcidHCID 596310392-Chloro-5-morpholinopyridin-3-amine

生成物 1

HCID 596313095'-Methoxy-5-morpholino-2,3'-bipyridin-3-amine

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-5-morpholinopyridin-3-amine (0.26 g, 1.2 mmol), 5-methoxypyridin-3-ylboronic acid (0.24 g, 1.6 mmol), tricyclohexylphosphine (42.7 mg, 0.15 mmol), and tris(dibenzylideneacetone)dipalladium (0) (68.4 mg, 0.075 mmol) were added to a flask then degassed and backfilled with argon. To the flask, 1,4-dioxane (5.0 mL) and aq. 1.3M potassium phosphate tribasic (2.3 mL, 3 mmol) were added by syringe. The resulting reaction was heated to 90° C. and monitored with TLC and LC-MS. After 19 h, the reaction was cooled to rt then poured into water. After extracting twice with EtOAc and twice with DCM, the combined organic extractions were dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on basic alumina (0-100% EtOAc in hexanes) to afford a brown solid as 5′-methoxy-5-morpholino-2,3′-bipyridin-3-amine. Mass Spectrum (pos.) m/e: 287.2 (M+1).

後処理

  1. customthen degassed
  2. customThe resulting reaction
  3. temperaturethe reaction was cooled to rt
  4. extractionAfter extracting twice with EtOAc and twice with DCM
  5. extractionthe combined organic extractions
  6. dry with materialwere dried over anhydrous magnesium sulfate
  7. filtrationAfter filtration and concentration
  8. customthe residue was purified on basic alumina (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-162e5d7f851049d29b3dbd3f52cc2f76
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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