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

HRID 2284453노트

반응식

HRID 2284453 반응식
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

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 2734323(3-Chlorophenyl)boronic acidHCID 86658330HCID 86658330, 화합물

생성물 1

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

시약·촉매·용매 2

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-702531c4cb5d465097c5ed8341f8911a
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09145418B2

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