Methoxymethyl-triphenylphosphonium chloride → 5-bromo-3-[1-(2-ethyl-2H-pyrazol-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine

HRID 2234667ノート

反応式

HRID 2234667 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH2:34][C:35]1[C:40]([C:41]([C:43]2[N:44]([CH2:48][CH3:49])[N:45]=[CH:46][CH:47]=2)=O)=[CH:39][C:38]([Br:50])=[CH:37][N:36]=1>O1CCCC1>[Br:50][C:38]1[CH:39]=[C:40]([C:41]([C:43]2[N:44]([CH2:48][CH3:49])[N:45]=[CH:46][CH:47]=2)=[CH:2][O:3][CH3:4])[C:35]([NH2:34])=[N:36][CH:37]=1

参加物

5

反応物 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 57731574(2-amino-5-bromo-pyridin-3-yl)-(2-ethyl-2H-pyrazol-3-yl)-methanone

生成物 1

HCID 686918565-bromo-3-[1-(2-ethyl-2H-pyrazol-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine収率 75.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (methoxymethyl)triphenylphosphonium chloride (866 mg, 2.53 mmol) in tetrahydrofuran (20 ml) was added potassium bis(trimethylsilyl)amide (5.0 ml, 0.5M, 2.5 mmol). The red-orange reaction mixture was stirred at room temperature for 45 minutes. A solution of (2-amino-5-bromo-pyridin-3-yl)-(2-ethyl-2H-pyrazol-3-yl)-methanone (339 mg, 1.15 mmol) in tetrahydrofuran (10 ml) was added to the reaction mixture. The combined solution was stirred for 4 hours, and then quenched with saturated, aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes) to give 280 mg (75%) of 5-bromo-3-[1-(2-ethyl-2H-pyrazol-3-yl)-2-methoxy-vinyl]-pyridin-2-ylamine. MS: m/z 323.2+325.2 (M+H+).

後処理

  1. stirringThe combined solution was stirred for 4 hours
  2. customquenched with saturated, aqueous ammonium chloride
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (0 to 100% [10% methanol in ethyl acetate] in hexanes)

出典と根拠

ORDレコード
ord-2715ec34cbe74aa99444226c91fd53dc
出典データセット
uspto-grants-2010_05
特許番号
US07709645B2

反応ノート

読み込み中…