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

HRID 226116

반응식

HRID 226116 반응식
[CH3:1][CH2:2][CH2-:3].[Mg+2].[Br-].CON(C)[C:9]([C:11]1[C:12]2[N:13]([C:18]([C:22]3[S:26][C:25]4[CH:27]=[CH:28][C:29]([F:31])=[CH:30][C:24]=4[C:23]=3[CH3:32])=[C:19]([CH3:21])[N:20]=2)[N:14]=[C:15]([CH3:17])[CH:16]=1)=[O:10]>C1COCC1>[F:31][C:29]1[CH:28]=[CH:27][C:25]2[S:26][C:22]([C:18]3[N:13]4[N:14]=[C:15]([CH3:17])[CH:16]=[C:11]([C:9](=[O:10])[CH2:1][CH2:2][CH3:3])[C:12]4=[N:20][C:19]=3[CH3:21])=[C:23]([CH3:32])[C:24]=2[CH:30]=1

참가 물질

4

반응물 2

HCID 101916BromopropylmagnesiumHCID 866210453-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-8-carboxylic acid methoxy-methyl-amide

생성물 1

HCID 688590651-[3-(5-Fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-8-yl]-butan-1-one수율 463.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-Propylmagnesium bromide (0.303 g, 2.06 mmol) is added dropwise to a solution of 3-(5-fluoro-3-methyl-benzo[b]thiophen-2-yl)-2,6-dimethyl-imidazo[1,2-b]pyridazine-8-carboxylic acid methoxy-methyl-amide (0.21 g, 0.52 mmol) in THF (5 mL) at 0° C. The reaction is stirred at room temperature overnight. The mixture is quenched with H2O, extracted with CH2Cl2, dried over sodium sulfate, filtered, and concentrated to dryness. The crude is purified through an ISCO column (5-10% EtOAc/Hexane) to give the title compound (0.92 g, 42%). 1H NMR (CDCl3): δ 7.8 (dd, J=4.8, 8.5 Hz, 1H), 7.5 (dd, J=2.5, 9.7 Hz, 1H), 7.4 (s, 1H), 7.2 (m, 1H), 3.6 (t, J=5.7, 2H), 2.6 (s, 3H), 2.55 (s, 3H), 2.3 (s, 3H), 1.9 (m, 2H), 1.1 (t, J=7.5, 3H) ppm. MS (m/e): 382 (M+1).

후처리

  1. customThe mixture is quenched with H2O
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe crude is purified through an ISCO column (5-10% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-6fda92cc3b3b47ec977a3e89d2c84380
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557103B2

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