Aluminium lithium hydride → 5-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzylamine

HRID 1715604ノート

反応式

HRID 1715604 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[C:15]([CH3:18])=[N:16][O:17][C:13]=3[CH:12]=2)=[C:6]([CH:9]=1)[C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][C:11]2[CH:20]=[CH:19][C:14]3[C:15]([CH3:18])=[N:16][O:17][C:13]=3[CH:12]=2)=[C:6]([CH:9]=1)[CH2:7][NH2:8]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 574841185-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile

生成物 1

HCID 574841195-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzylamine収率 78.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

5-fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile (3v) (84 mg, 0.31 mmol; prepared as described in Example 108) was dissolved in THF (3 mL) and cooled to 0° C. A solution of lithium aluminum hydride in THF (0.35 mL, 0.35 mmol) was added slowly and the reaction was allowed to warm to room temperature. After 1 hour the reaction was quenched by the portion-wise addition of sodium sulfate decahydrate at 0° C. until gas evolution ceased. THF was added and the mixture was filtered through celite and eluted with EtOAc. The solution was concentrated to provide crude product (9v) (66 mg) which was used without further purification.

後処理

  1. temperatureto warm to room temperature
  2. customAfter 1 hour the reaction was quenched by the portion-wise addition of sodium sulfate decahydrate at 0° C. until gas evolution
  3. additionTHF was added
  4. filtrationthe mixture was filtered through celite
  5. washeluted with EtOAc
  6. concentrationThe solution was concentrated

出典と根拠

ORDレコード
ord-85bc8a92b57943b5bb20adf295f5ddd5
出典データセット
uspto-grants-2010_09
特許番号
US07799782B2

反応ノート

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