Bromopropylmagnesium → 4-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-ol

HRID 226117

반응식

HRID 226117 반응식
[CH3:1][CH2:2][CH2-:3].[Mg+2].[Br-].[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24](=[O:28])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1>C1COCC1>[F:6][C:7]1[CH:32]=[CH:31][C:10]2[S:11][C:12]([C:15]3[N:19]4[N:20]=[C:21]([CH3:29])[CH:22]=[C:23]([C:24]([OH:28])([CH2:1][CH2:2][CH3:3])[CH2:25][CH2:26][CH3:27])[C:18]4=[N:17][C:16]=3[CH3:30])=[C:13]([CH3:14])[C:9]=2[CH:8]=1

참가 물질

4

반응물 2

HCID 101916BromopropylmagnesiumHCID 688590651-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one

생성물 1

HCID 577526054-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-heptan-4-ol수율 24.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-Propylmagnesium bromide (0.601 g, 4.09 mmol) is added dropwise to a solution of 1-[3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one (1.08 g, 2.72 mmol) in THF (27 mL) at 0° C. The reaction is stirred at room temperature overnight. The mixture is quenched with ammonium chloride, extracted with ethylacetate, dried over sodium sulfate, filtered, and concentrated to dryness. The crude is purified by ISCO (5% EtOAc/Hexane) to give the title compound (280 mg, 24%). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.2 (m, 1H), 6.7 (s, 1H), 6.4 (s, 1H), 2.6 (s, 3H), 2.5 (s, 3H), 2.3 (s, 3H), 2.0 (m, 3H), 1.5 (m, 1H), 1.3 (m, 4H), 0.9 (t, J=7.3, 6H) ppm. Mass spectrum (m/e): 426 (M+1).

후처리

  1. customThe mixture is quenched with ammonium chloride
  2. extractionextracted with ethylacetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude is purified by ISCO (5% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-8293ec1e86804ceb9c52eb4835f4370c
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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