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5-Chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate → 1-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone

HRID 1192508
ノート
印刷プレビュー

反応式

HRID 1192508 の反応式
[Cl:1][C:2]1[CH:11]=[C:10]([C:12](N(OC)C)=[O:13])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.F[C:26](F)(F)S(OC1C(C(N(OC)C)=O)=CC(Cl)=C2C=1N=CC=C2)(=O)=O.C[Mg]Br>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]([C:12](=[O:13])[CH3:26])[C:9]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 866561725-Chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonateHCID 866561795-chloro-8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 672483691-[5-Chloro-8-(3-fluorophenyl)quinolin-7-yl]ethanone収率 32.8%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

To a mixture of 5-chloro-8-(3-fluorophenyl)-N-methoxy-N-methylquinoline-7-carboxamide (154 mg, 0.447 mmol) and 5-chloro-7-{[methoxy(methyl)amino]carbonyl}quinolin-8-yl trifluoromethanesulfonate (154 mg, 0.386 mmol) in tetrahydrofuran (1 mL) was added 1.40 M methylmagnesium bromide in tetrahydrofuran (3.8 mL, 5.3 mmol). The reaction was stirred at room temperature overnight, quenched with saturated ammonium chloride, and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resultant residue was purified on silica gel, eluting with 0 to 50% of EtOAc in hexane, to give the desired product (38 mg, 32%). LCMS calculated for C17H12ClFNO(M+H)+: m/z=300.1; found: 300.0.

後処理

  1. customquenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resultant residue was purified on silica gel
  7. washeluting with 0 to 50% of EtOAc in hexane

出典と根拠

ORDレコード
ord-62f955ff1de541648bead7b0a6ce1939
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08680108B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート