Lawesson's reagent → 6-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

HRID 1521672ノート

反応式

HRID 1521672 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=O)[CH2:6][CH2:5]2.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([F:12])[CH:11]=1)[NH:8][C:7](=[S:23])[CH2:6][CH2:5]2

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 709774606-BROMO-8-FLUORO-3,4-DIHYDROQUINOLIN-2(1H)-ONE

生成物 1

HCID 891560716-bromo-8-fluoro-3,4-dihydroquinoline-2(1H)-thione

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a suspension of 6-bromo-8-fluoro-3,4-dihydroquinolin-2(1H)-one (157-3, 2.00 g, 8.19 mmol) in toluene (50 mL) was added Lawesson's reagent (1.66 g, 4.10 mmol). After reflux for 2 h, toluene was distilled off to yield the crude product, which was then purified by flash chromatography on silica gel to obtain title compound (yellow solid). 1H NMR (DMSO-D6, 500 MHz) 6=12.14 (s, 1H), 7.46 (dd, J=2.0 Hz, JHF=10.0 Hz, 1H), 7.34 (s, 1H), 2.94 (d, J=8.0 Hz, 2H), 2.84 (d, J=8.0 Hz, 2H).

後処理

  1. temperatureAfter reflux for 2 h
  2. distillationtoluene was distilled off
  3. customto yield the crude product, which
  4. customwas then purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-35ec05a85adb49018ad1c36f32c1bbc0
出典データセット
uspto-grants-2015_07
特許番号
US09073929B2

反応ノート

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