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1-Benzylpiperazine → 8-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester

HRID 206
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HRID 206 반응식
CCOC(=O)c1cc(=O)c2cc(OC)cc(Br)c2o1.c1ccc(CN2CCNCC2)cc1>Cc1ccccc1.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].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CCOC(=O)c1cc(=O)c2cc(OC)cc(N3CCN(Cc4ccccc4)CC3)c2o1
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참가 물질

7

반응물 2

HCID 759941-BenzylpiperazineHCID 22142256ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate

생성물 1

HCID 689747878-(4-Benzyl-piperazin-1-yl)-6-methoxy-4-oxo-4H-chromene-2-carboxylic acid ethyl ester수율 48.39%

시약·촉매·용매 4

HCID 10796Cesium carbonate시약HCID 634876Binap, (A+-)-촉매
HCID 9811564Bis(dibenzylideneacetone)palladium촉매
HCID 1140Toluene용매

반응 조건

온도
80 °C

실험 절차

Tris(dibenzylideneacetone)dipalladium(0) (0.280 g, 0.31 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.457 g, 0.73 mmol), ethyl 8-bromo-6-methoxy-4-oxo-4H-chromene-2-carboxylate (2 g, 6.11 mmol), 1-benzylpiperazine (1.169 mL, 6.73 mmol) and cesium carbonate (2.79 g, 8.56 mmol) were heated under argon to 80 °C in toluene (60 mL) overnight. The reaction mixture was allowed to cool. Ethylacetate was added and the organic mixture was filtered. The filtrate was evaporated onto Silica gel. The crude product was added to a silica gel column and was eluted with MeOH/DCM 0-5%. 1H NMR in CDCl3 is consistent with desired product MS (m+1) = 423. HPLC Peak RT = 3.38 minutes is product. Purity = 63%.

출처 및 근거

ORD 기록
ord-a7f71cce88db46cba0388c01927b5a88
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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