Tetraethylammonium → Ethyl 2-(6-cyano-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

HRID 13645

반응식

HRID 13645 반응식
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]([CH3:13])[C:4](=[O:14])[C:3]=1[C:15]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16].[CH2:24]([N+:26](CC)(CC)CC)C>O1CCOCC1.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[Cu].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:24]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]([CH3:13])[C:4](=[O:14])[C:3]([C:15]([NH:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])=[C:2]2[OH:1])#[N:26]

참가 물질

7

반응물 2

HCID 5413TetraethylammoniumHCID 54712173Ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

생성물 1

HCID 59340060Ethyl 2-(6-cyano-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate수율 90%

시약·촉매·용매 4

HCID 23978Copper촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매2회

반응 조건

온도
145 °C

실험 절차

Ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.200 g, 0.46 mmol), 1,1′-bis(diphenylphosphino)ferrocene (0.048 g, 0.087 mmol), Copper cyamide (0.194 g, 2.2 mmol) and Tris(dibenzylideneacetone)dipalladium (0.020 g, 0.022 mmol) in 1,4-dioxane (2 ml) were combined in a 10 ml tube. Tetraethylammonium cyamide (0.085 g, 0.54 mmol) and 1,4-dioxane (1 ml) were added and the tube was sealed and heated to 145° C. for 15 min under Argon in a microwave (Personal Chemistry 300 W). After cooling, the mixture was filtered and washed with methylene chloride (50 ml). The filtrate was washed with deionized water (3×50 ml), then with brine (50 ml), dried over magnesium sulfate then concentrated and dried in vacuo. Flash column chromatography (Silica gel, 0-100% methylene chloride in hexane) gave a solid which washed with diethyl ether, filtered and dried in vacuo to give ethyl 2-(6-cyano-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (0.135 g, 90% yield).

후처리

  1. customthe tube was sealed
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. washwashed with methylene chloride (50 ml)
  5. washThe filtrate was washed with deionized water (3×50 ml)
  6. dry with materialwith brine (50 ml), dried over magnesium sulfate
  7. concentrationthen concentrated
  8. customdried in vacuo
  9. customFlash column chromatography (Silica gel, 0-100% methylene chloride in hexane) gave a solid which
  10. washwashed with diethyl ether
  11. filtrationfiltered
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-20c47747d4944f5c96f2dc4f1765c73b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728130B2

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