1-Benzylpiperazine → Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate

HRID 231노트

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HRID 231 반응식
CCOC(=O)c1cc2c(Br)cccc2o1.c1ccc(CN2CCNCC2)cc1>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CCOC(=O)c1cc2c(N3CCN(Cc4ccccc4)CC3)cccc2o1

참가 물질

7

반응물 2

HCID 759941-BenzylpiperazineHCID 21838105Ethyl 4-bromobenzofuran-2-carboxylate

생성물 1

HCID 67982691Ethyl 4-(4-benzylpiperazin-1-yl)benzofuran-2-carboxylate수율 90.08%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl촉매HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

20/10 2009 10:10:14 +0200 To ethyl 4-bromobenzofuran-2-carboxylate (2.50 g, 9.29 mmol) and 1-benzylpiperazine (1.776 mL, 10.22 mmol) in dry degassed dioxane (30 mL) were added Cesium carbonate (3.94 g, 12.08 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.443 g, 0.93 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.425 g, 0.46 mmol) under argon and the reaction heated at 95°C o/n. All starting material consumed. The crude solution was pooled with the corresponding solution in EN03307-46 Water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (MgSO4), filtered and evaporated. The crude was purified by flash chrom. (SiO2; Heptane/EtOAc 70/30) to give 3.05 g (50%) of the product as a yellow solid.

출처 및 근거

ORD 기록
ord-971fd86c0ca2434fb005b5350f485988
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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