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Nitrogen → 3-(1,5-dimethyl-1H-indol-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine

HRID 226089
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HRID 226089 반응식
[CH2:1]([CH:3]([C:6]1[C:7]2[N:8]([C:13](I)=[C:14]([CH3:16])[N:15]=2)[N:9]=[C:10]([CH3:12])[CH:11]=1)[CH2:4][CH3:5])[CH3:2].C([C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:29]=1[N:28]([CH3:30])[C:27](C)=[CH:26]2)(C)C.[C:32]([O-])([O-])=O.[Cs+].[Cs+].N#N>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].CCOC(C)=O.CN(C=O)C>[CH3:30][N:28]1[C:29]2[C:25](=[CH:24][C:23]([CH3:32])=[CH:22][CH:21]=2)[CH:26]=[C:27]1[C:13]1[N:8]2[N:9]=[C:10]([CH3:12])[CH:11]=[C:6]([CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])[C:7]2=[N:15][C:14]=1[CH3:16]
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참가 물질

8

반응물 4

HCID 947NitrogenHCID 10796Cesium carbonateHCID 577526818-(1-Ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 688581427-isopropyl-1,2-dimethyl-1H-indole

생성물 1

HCID 577526543-(1,5-dimethyl-1H-indol-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine수율 4.8%

시약·촉매·용매 3

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
130 °C

실험 절차

A solution of 8-(1-ethyl-propyl)-3-iodo-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.30 g, 0.87 mmol), 7-isopropyl-1,2-dimethyl-1H-indole (0.33 g, 1.76 mmol), Cs2CO3 (0.57 g, 1.75 mmol), and DMF (5 mL), is degassed with N2 for 20 minutes. Pd2(dba)3 (0.040 g, 0.044 mmol is added and the solution is heated at 130° C. overnight. The solution is diluted EtOAc (30 mL) washed with water (2×30 mL), brine (30 mL) dried over MgSO4, filtered and concentrated. The residue is purified by ISCO (20%-30% EtOAc gradient) to furnish the title compound (0.017 g, 0.042 mmol, 4.8%). 1H NMR (CDCl3), δ 1.14-1.46 (m, 6H), 1.76-1.95 (m, 4H), 2.30 (s, 3H), 2.42 (s, 3H), 2.45 (s, 3H), 3.38-3.48 (m, 1H), 3.86-3.97 (m, 1H), 4.04 (s, 3H), 6.64 (s, 1H), 6.99-7. LC/MS (m/z): calcd. for C26H34N4 (M+H)+: 403.3. found: 403.4.

후처리

  1. washwashed with water (2×30 mL), brine (30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by ISCO (20%-30% EtOAc gradient)

출처 및 근거

ORD 기록
ord-4b88e88b30e848ef86f7e9f09dd5565f
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557103B2

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