4-(2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline → HCID 67347550、化合物

HRID 1676374ノート

反応式

HRID 1676374 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=4[F:28])[CH:12]=3)=[CH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[H][H]>[Pd].CO>[O:4]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[S:19][C:18]4[C:13](=[N:14][CH:15]=[CH:16][C:17]=4[O:20][C:21]4[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][C:22]=4[F:28])[CH:12]=3)[CH2:7][CH2:6]2)[O:1][CH2:2][CH2:3]1

参加物

5

反応物 2

HCID 673482014-(2-(1,4-Dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67347550HCID 67347550、化合物収率 25.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

A round-bottomed flask was charged with 4-(2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline (Example 161, Step A, 50.0 mg, 0.125 mmol), palladium on carbon (44.6 mg, 0.0376 mmol, 10%) and MeOH (10 mL). The air was exchanged with nitrogen three times and then was exchanged with hydrogen another three times. Then the reaction mixture was stirred under hydrogen at room temperature until the starting material had been consumed (overnight). The mixture was filtrated to remove the palladium on carbon and then the solvent was removed under reduced pressure to afford crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (12.8 mg, 25.5%). LRMS (APCI pos): m/e 401 (M+1). 1H NMR (400 MHz, CDCl3) δ 8.40 (m, 1H), 7.25 (s, 1H), 7.02 (t, 1H), 6.42-6.60 (m, 3H), 4.00 (s, 4H), 3.81 (br s, 2H), 2.89 (m, 1H), 2.14 (m, 2H), 1.90 (m, 4H), 1.72 (m, 2H).

後処理

  1. customhad been consumed (overnight)
  2. filtrationThe mixture was filtrated
  3. customto remove the palladium on carbon
  4. customthe solvent was removed under reduced pressure
  5. customto afford crude product
  6. customThe crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1

出典と根拠

ORDレコード
ord-7f26115229e14b5db46af9aff0d746f3
出典データセット
uspto-grants-2011_08
特許番号
US08003662B2

反応ノート

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