Benzothiazole → 4-(Benzo[d]thiazol-2-yl(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile

HRID 2104948ノート

反応式

HRID 2104948 の反応式
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Li]CCCC.[CH2:15]([O:17][C:18]1[CH:19]=[C:20]([O:35][CH:36]([CH3:38])[CH3:37])[C:21]([F:34])=[C:22]([CH:33]=1)/[CH:23]=[N:24]/[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1)[CH3:16]>C1COCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:24]([CH2:23][C:22]1[CH:33]=[C:18]([O:17][CH2:15][CH3:16])[CH:19]=[C:20]([O:35][CH:36]([CH3:38])[CH3:37])[C:21]=1[F:34])[C:25]1[CH:32]=[CH:31][C:28]([C:29]#[N:30])=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 7222BenzothiazoleHCID 178418339ButyllithiumHCID 178466720HCID 178466720、化合物

生成物 1

HCID 688166324-(Benzo[d]thiazol-2-yl(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile収率 42.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a solution of benzothiazole (61.9 mg, 0.458 mmol) in 2 mL THF at −78° C. was added 1.6 M solution of BuLi in THF (315 μL, 0.504 mmol). The mixture was stirred at −78° C. for 45 min, then a solution of Intermediate 7.3 (149 mg, 0.458 mmol) in 0.5 mL THF was added dropwise. The mixture was stirred and allowed to warm to rt overnight, then was quenched with sat. NH4Cl. The mixture was diluted with EtOAc, washed with H2O and brine, dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient) to afford 90 mg of Intermediate 7.4 as a white solid.

後処理

  1. stirringThe mixture was stirred
  2. temperatureto warm to rt overnight
  3. customwas quenched with sat. NH4Cl
  4. additionThe mixture was diluted with EtOAc
  5. washwashed with H2O and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (0 to 50% EtOAc/hexanes gradient)

出典と根拠

ORDレコード
ord-5b91879fcf2842bc87e613742167ebbb
出典データセット
uspto-grants-2009_08
特許番号
US07576098B2

反応ノート

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