3-(Bromomethyl)-4-fluorobenzonitrile → 4-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrile

HRID 1098657ノート

反応式

HRID 1098657 の反応式
[F:1][C:2]1[C:3]([CH3:20])=[CH:4][C:5]2[C:6]3[C:7]4[CH:19]=[CH:18][CH:17]=[N:16][C:8]=4[O:9][C:10](=[O:15])[C:11]=3[NH:12][C:13]=2[CH:14]=1.Br[CH2:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[F:31])[C:26]#[N:27]>CN(C=O)C.C(OCC)(=O)C>[F:31][C:30]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH2:22][N:12]1[C:11]2[C:10](=[O:15])[O:9][C:8]3[N:16]=[CH:17][CH:18]=[CH:19][C:7]=3[C:6]=2[C:5]2[CH:4]=[C:3]([CH3:20])[C:2]([F:1])=[CH:14][C:13]1=2

参加物

5

反応物 2

HCID 162272363-(Bromomethyl)-4-fluorobenzonitrileHCID 581324399-Fluoro-10-methyl-7H-5-oxa-4,7-diaza-benzo[c]fluoren-6-one

生成物 1

HCID 581327234-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrile収率 80.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 9-Fluoro-10-methyl-7H-5-oxa-4,7-diaza-benzo[c]fluoren-6-one 1G (167 mg, 0.622 mmol) in DMF (3.0 mL) was added 3-Bromomethyl-4-fluoro-benzonitrile (160.0 mg, 0.747 mmol) and CsCO3 (243 mg, 0.747 mmol) at room temperature and the reaction mixture was allowed to stir overnight. The reaction mixture was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The concentrated crude was purified using chromatography over SiO2 using 0 to 30% ethyl acetate in hexane to provide 4-Fluoro-3-(9-fluoro-10-methyl-6-oxo-6H-5-oxa-4,7-diaza-benzo[c]fluoren-7-ylmethyl)-benzonitrile 1H (200 mg, 80%). M.S. found for C23H13F2N3O2: 402.9 (M+H)+.

後処理

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. concentrationThe concentrated crude
  6. customwas purified

出典と根拠

ORDレコード
ord-0479143dc2cb464a8523d5887260b7ee
出典データセット
uspto-grants-2012_03
特許番号
US08143305B2

反応ノート

読み込み中…