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Hexane → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-difluorophenyl)oxindole

HRID 1369109
ノート
印刷プレビュー

反応式

HRID 1369109 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[F:9].[Li]CCCC.CCCCCC.[CH2:21]([N:23]([CH2:42][CH3:43])[CH2:24][CH2:25][N:26]1[C:36]2[C:31](=[C:32]([C:38]([F:41])([F:40])[F:39])[CH:33]=[C:34]([I:37])[CH:35]=2)[C:29](=[O:30])[C:27]1=[O:28])[CH3:22]>C1COCC1>[CH2:42]([N:23]([CH2:21][CH3:22])[CH2:24][CH2:25][N:26]1[C:36]2[C:31](=[C:32]([C:38]([F:39])([F:41])[F:40])[CH:33]=[C:34]([I:37])[CH:35]=2)[C:29]([OH:30])([C:2]2[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=2[F:9])[C:27]1=[O:28])[CH3:43]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8058HexaneHCID 676741-Bromo-2,4-difluorobenzeneHCID 110265521-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodoisatinHCID 178418339Butyllithium

生成物 1

HCID 185185481-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2,4-difluorophenyl)oxindole収率 91.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

To a solution of 1-bromo-2,4-difluorobenzene (0.13 mL, 1.15 mmol) in THF (7.5 mL) was added dropwise 1.47 N BuLi in hexane (0.77 mL, 1.13 mmol) at −78° C. and the mixture was stirred for 15 min. To the resulting solution was added dropwise a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodoisatin (500 mg, 1.14 mmol) in THF (6 mL) over 15 min at −78° C. The mixture was stirred for 40 min at the same temperature and the reaction was quenched with aqueous NaHCO3. The mixture was extracted with ethyl acetate and the extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (576 mg, 91%).

後処理

  1. stirringThe mixture was stirred for 40 min at the same temperature
  2. customthe reaction was quenched with aqueous NaHCO3
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol

出典と根拠

ORDレコード
ord-4fcf88a7d5514c4ba35a2a282486b947
出典データセット
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06576656B1

反応ノート

読み込み中…

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