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

反応式

HRID 226116 の反応式
[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

参加物

4

反応物 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

生成物 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-one収率 463.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6fda92cc3b3b47ec977a3e89d2c84380
出典データセット
uspto-grants-2009_07
特許番号
US07557103B2

関連ノート

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