Methanol → 8-fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one

HRID 1844042ノート

反応式

HRID 1844042 の反応式
[N-:1]=[N+]=[N-].[Na+].[F:5][C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[CH2:12][CH2:11]2.CO>C(O)(C(F)(F)F)=O.C(Cl)(Cl)Cl>[F:5][C:6]1[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=[C:10]2[C:14]=1[C:13](=[O:15])[NH:1][CH2:12][CH2:11]2

参加物

6

反応物 3

HCID 887MethanolHCID 33557Sodium AzideHCID 668036517-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one

生成物 1

HCID 668020098-fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one収率 56.1%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

Sodium azide (492 mg, 7.5688 mmol) was added portion wise to a stirred solution of 7-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one (I-77c: 500 mg, 2.2935 mmol) in TFA (15 mL) over a period of 5 hours at 80° C. The reaction was monitored by TLC (5% methanol in CHCl3). The reaction mixture was concentrated under reduced pressure, followed by the addition of ice. The precipitated solid was filtered, washed with water (20 mL) and dried under reduced pressure to yield the crude product. Purification by column chromatography on silica gel (2% methanol in CHCl3) afforded 300 mg of the product (56.1% yield).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionfollowed by the addition of ice
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water (20 mL)
  5. customdried under reduced pressure
  6. customto yield the crude product
  7. customPurification by column chromatography on silica gel (2% methanol in CHCl3)

出典と根拠

ORDレコード
ord-66240a63a9f14aa29336f30e9a86d8d7
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

反応ノート

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