Cesium carbonate → 5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one

HRID 2069734ノート

反応式

HRID 2069734 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Br[C:13]1[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=[C:17]([Br:19])[CH:18]=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>O1CCOCC1.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:19][C:17]1[CH:18]=[C:13]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]([OH:11])([CH3:9])[CH3:10])=[CH:6][N:7]=2)[C:14](=[O:21])[N:15]([CH3:20])[CH:16]=1

参加物

8

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 594737712-(6-Aminopyridin-3-yl)propan-2-ol

生成物 1

HCID 594737935-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one収率 60.3%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

In a flame-dried seal tube reaction vial, dissolve 2-(6-Amino-pyridin-3-yl)-propan-2-ol (530 mg, 3.484 mmol) in anhydrous Dioxane (13 mL). Then add 3,5-Dibromo-1-methyl-1H-pyridin-2-one (1.022 g, 3.83 mmol), Cs2CO3 (3.4 g, 10.45 mmol) and Xantphos (0.2 g, 0.3482 mmol). Bubble argon through for 15 min before adding Pd(OAc)2 (39 mg, 0.1742 mmol). The tube as sealed and heated to 120° C. Reaction was kept at that temperature for 6 hrs. Reaction was then diluted with EtOAc (10 mL) and filtered through celite. Filter cake was washed with EtOAc (3×10 mL). The combined filtrate was concentrated and purified on ISCO column with 5-10% MeOH in 1/1 EtOAC/Hexane to afford 5-Bromo-3-[5-(1-hydroxy-1-methyl-ethyl)-pyridin-2-ylamino]-1-methyl-1H-pyridin-2-one (710 mg, yield 60%) as green solid.

後処理

  1. customIn a flame-dried seal tube
  2. customreaction vial
  3. customThe tube as sealed
  4. customReaction
  5. customReaction
  6. filtrationfiltered through celite
  7. filtrationFilter cake
  8. washwas washed with EtOAc (3×10 mL)
  9. concentrationThe combined filtrate was concentrated
  10. custompurified on ISCO column with 5-10% MeOH in 1/1 EtOAC/Hexane

出典と根拠

ORDレコード
ord-d6cc6ff042694801a73e352d2450de0e
出典データセット
uspto-grants-2012_10
特許番号
US08299077B2

反応ノート

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