Dichloromethane → Ethyl [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate

HRID 2284453ノート

反応式

HRID 2284453 の反応式
I[C:2]1[CH:3]=[C:4]2[C:9](=[O:10])[NH:8][CH2:7][CH:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]2[CH:17]=1.[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].ClCCl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCOCC1.O>[Cl:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:3]=[C:4]3[C:9](=[O:10])[NH:8][CH2:7][CH:6]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:5]3[CH:17]=2)[CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86658330HCID 86658330、化合物

生成物 1

HCID 86731547Ethyl [7-(3-chlorophenyl)-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl]acetate収率 60%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

To a solution of ethyl (7-iodo-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate (1.00 g, 2.87 mmol) in a degassed (with Ar stream) mixture of 1,4-dioxane/H2O (25/5 mL) 3-chloro-phenylboronic acid (898 mg, 5.74 mmol), cesium carbonate (2.807 g, 8.61 mmol), and at the end 1,1′-bis(diphenylphosphino)ferrocenepalladium(II) dichloride, complex with dichloromethane (1:1) (234 mg 0.287 mmol) were added. The reaction mixture was capped under argon atmosphere and stirred at 80° for 2 h. The solvent was evaporated under vacuum and the residue partitioned between ethyl acetate and water. The organic phase was dried on Na2SO4 and concentrated to dryness. The crude was purified by chromatography on a silica gel column (eluent: DCM/EtOAc/EtOH: 60/35/5) to afford 0.573 g (60% yield) as a light brown solid.

後処理

  1. customThe reaction mixture was capped under argon atmosphere
  2. customThe solvent was evaporated under vacuum
  3. customthe residue partitioned between ethyl acetate and water
  4. customThe organic phase was dried on Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe crude was purified by chromatography on a silica gel column (eluent: DCM/EtOAc/EtOH: 60/35/5)
  7. customto afford 0.573 g (60% yield) as a light brown solid

出典と根拠

ORDレコード
ord-702531c4cb5d465097c5ed8341f8911a
出典データセット
uspto-grants-2015_09
特許番号
US09145418B2

反応ノート

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