Lithium Hydroxide → HCID 67036415、化合物

HRID 1623479ノート

反応式

HRID 1623479 の反応式
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH3:21])[C:12]2=[O:29])[CH:5]=1.[OH-].[Li+]>C1COCC1.O>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:20](=[C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:30])=[O:2])[C:12]2=[O:29])[CH3:21])=[CH:27][CH:26]=1

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 67036322HCID 67036322、化合物

生成物 1

HCID 67036415HCID 67036415、化合物収率 31.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid methyl ester (0.33 g, 0.82 mmol) was dissolved in THF 5 ml. Then a solution of lithium hydroxide (0.35 g, 8.2 mmol) in water (2.0 ml) was added. After stirring for 12 hours, the solvent was removed under reduced pressure. The residue was dissolved in 2 ml DMF for prepared HPLC to give 3-{3-[1-(4-fluoro-phenyl)-ethylidene]-2-oxo-2,3-dihydro-indol-1-ylmethyl}-benzoic acid as yellow powder (100 mg). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.78 (s, 3H) 5.06 (s, 2H) 6.08 (d, J=7.83 Hz, 1H) 6.68 (t, J=7.45 Hz, 1H) 6.92 (d, J=7.83 Hz, 1H) 7.11 (t, J=7.45 Hz, 1H) 7.38 (t, J=8.84 Hz, 2H) 7.43-7.51 (m, 1H) 7.46 (dd, J=8.72, 5.68 Hz, 2H) 7.60 (d, J=7.58 Hz, 1H) 7.85 (d, J=7.83 Hz, 1H) 7.92 (s, 1H) 13.03 (s, 1H). MS calcd. for C24H18FNO3 387.4, obsd. (ESI+) [(M+H)+] 388.2.

後処理

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 2 ml DMF
  3. customfor prepared HPLC

出典と根拠

ORDレコード
ord-0d39b84786324e2a85dcec9ecf80b75c
出典データセット
uspto-grants-2014_07
特許番号
US08778973B2

反応ノート

読み込み中…