N,N'-Dimethylethylenediamine → HCID 59375096, 화합물

HRID 661829노트

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HRID 661829 반응식
[F:1][C:2]1[C:3](I)=[N:4][CH:5]=[CH:6][C:7]=1[I:8].[C:10]1(=[O:19])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12][NH:11]1.C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[F:1][C:2]1[C:3]([N:11]2[CH2:12][C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]2=[O:19])=[N:4][CH:5]=[CH:6][C:7]=1[I:8]

참가 물질

7

반응물 4

HCID 8070N,N'-DimethylethylenediamineHCID 10199PhthalimidineHCID 11430Potassium CarbonateHCID 99979273-Fluoro-2,4-diiodopyridine

생성물 1

HCID 59375096HCID 59375096, 화합물수율 41%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A mixture of 3-fluoro-2,4-diiodopyridine (300 mg, 0.860 mmol), isoindolin-1-one (114 mg, 0.860 mmol), copper (I) iodide (8.19 mg, 0.043 mmol), potassium carbonate (238 mg, 1.720 mmol) and N1,N2-dimethylethane-1,2-diamine (7.58 mg, 0.086 mmol) in 1,4-dioxane (5 mL) was heated at 110° C. in a sealed tube for 15 h. The mixture was cooled to rt, filtered through Celite and washed with DCM. The filtrate was concentrated and the residue was purified by column chromatography (eluting with a gradient from 80:20 hexane-EtOAc to EtOAc) to give 2-(3-fluoro-4-iodopyridin-2-yl)isoindolin-1-one (125 mg, 41%). 1H NMR (400 MHz, chloroform-d) δ 7.86-8.06 (2H, m), 7.41-7.71 (4H, m), 5.04 (2H, s). Mass spectrum m/z 354.9 (M+H)+.

후처리

  1. temperatureThe mixture was cooled to rt
  2. filtrationfiltered through Celite
  3. washwashed with DCM
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography (
  6. washeluting with a gradient from 80:20 hexane-EtOAc to EtOAc)

출처 및 근거

ORD 기록
ord-09e0918f7a6f41cb9be9192dac7b3517
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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