Borane;tetrahydrofuran → HCID 59395056、化合物

HRID 1915508ノート

反応式

HRID 1915508 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](O)([C:12]([F:15])([F:14])[F:13])[C:7](=O)[NH:8]2)=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.CN(C=O)C>[F:15][C:12]([F:13])([F:14])[C:6]1[C:5]2[C:9](=[CH:10][C:2]([NH2:1])=[CH:3][CH:4]=2)[NH:8][CH:7]=1

参加物

5

反応物 2

HCID 2723981Borane;tetrahydrofuranHCID 59395032HCID 59395032、化合物

生成物 1

HCID 59395056HCID 59395056、化合物収率 60%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 6-amino-3-hydroxy-3-(trifluoromethyl)indolin-2-one (58 mg, 0.25 mmol) in THF (0.5 mL) at 0° C. was added BH3.THF complex (1 M in THF, 1 mL, 0.95 mmol) dropwise. The reaction mixture was stirred for 5 min at 0° C. then for 3 h at room temperature. The reaction mixture was quenched by adding very carefully 6M HCl (3.5 mL) until no more gas release was observed. The reaction mixture was then stirred at 80° C. for 2 h. The solvent was removed under reduce pressure and the solid residue obtained was dissolved in DMF (3 mL), filtered and purified by reverse phase HPLC (10-99% CH3CN/H2O) to provide 3-(trifluoromethyl)-1H-indol-6-amine (30 mg, 54%, TFA salt).

後処理

  1. waitfor 3 h at room temperature
  2. customThe reaction mixture was quenched
  3. additionby adding very carefully 6M HCl (3.5 mL) until no more gas release
  4. stirringThe reaction mixture was then stirred at 80° C. for 2 h
  5. customThe solvent was removed
  6. customthe solid residue obtained
  7. filtrationfiltered
  8. custompurified by reverse phase HPLC (10-99% CH3CN/H2O)

出典と根拠

ORDレコード
ord-d9b9272a9007430a80c1e8eb26ae6158
出典データセット
uspto-grants-2013_12
特許番号
US08614327B2

反応ノート

読み込み中…