반응식
CC(C)N1CCNCC1.CCOC(=O)c1cnc2cc(OCC)c(Br)cc2c1Nc1ccc(F)cc1F>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)c1cnc2cc(OCC)c(N3CCN(C(C)C)CC3)cc2c1Nc1ccc(F)cc1F참가 물질
6
반응물 2
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- 110 °C
실험 절차
To a solution of ethyl 6-bromo-4-(2,4-difluorophenylamino)-7-ethoxyquinoline-3-carboxylate (400 mg, 0.89 mmol) and 1-(Isopropyl)piperazine (254 µl, 1.77 mmol) in dioxane was added cesium carbonate (722 mg, 2.22 mmol), tris(dibenzylideneacetone)dipalladium(0) (40.6 mg, 0.04 mmol) and rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (55.2 mg, 0.09 mmol). Reaction vessel in oil bath set to 110 °C. 11am After 5 hours, MS shows product (major peak 499), and SM (minor peak 453). o/n, MS shows product peak. Reaction cooled, concentrated onto silica, and purified on ISCO. 40g column, 1:1 EA:Hex, then 100% EA. 289mg yellow solid. NMR (EN00180-62-1) supports product, but some oxidised BINAP impurity (LCMS 655).
출처 및 근거
- ORD 기록
- ord-56b1f4bfeebc4b8ab990b9804e798aa7
- 출처 데이터셋
- 750 AstraZeneca ELN dataset
- 원본 링크
- 출처 보기
연결된 노트
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