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Benzenamine, 4-fluoro-N-(1-methylethyl)- → 4-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde

HRID 2046069
ノート
印刷プレビュー

反応式

HRID 2046069 の反応式
O[CH2:2][C:3]1[S:7][C:6]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[F:16][C:17]1[CH:26]=[CH:25][C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=1>C(Cl)Cl.CCN(CC)CC.C1(C)C=CC=CC=1>[F:16][C:17]1[CH:26]=[CH:25][C:20]([N:21]([CH2:2][C:3]2[S:7][C:6]([C:8]3[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=3)=[CH:5][CH:4]=2)[CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-HCID 870750204-(5-(Hydroxymethyl)thiophen-2-yl)benzaldehyde

生成物 1

HCID 866606114-(5-(((4-Fluorophenyl)(isopropyl)amino)methyl)thiophen-2-yl)benzaldehyde収率 20%

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒
HCID 8471
Triethylamine
溶媒

実験手順

To a stirred solution of the product of Step A (0.436 g, 2 mmol) in anhydrous CH2Cl2 (10 ml) and Et3N (0.3 ml) mesyl chloride (0.4 ml) was added at 0° C. and stirring was continued for 1 h. The solvents were evaporated to dryness under reduced pressure and the residue was diluted to 50 ml with EtOAc and washed with H2O. The organic layer was separated and dried over MgSO4 and filtered. The filtrate was evaporated to give the crude product (0.63 g) as pale paste, which was taken up in anhydrous toluene and 4-fluoro-N-isopropylaniline (0.5 ml) was added to it. The mixture was stirred overnight at reflux and the solvent was evaporated. The residue was purified by FCC (SiO2, hexane/EtOAc) to give the title compound (0.14 g, 20%), as light creamy paste. 1H-NMR (CDCl3) 9.98 (s, 1H); 7.82 (d, 2H, J=8.31 Hz); 7.66 (d, 2H, J=8.31 Hz); 7.28 (d, 1H, J=3.69 Hz); 6.93-6.86 (m, 3H); 6.81-6.76 (m, 2H); 4.79 (s, 2H); 4.08-3.99 (m, 1H); 1.22 (d, 6H, J=6.6 Hz).

後処理

  1. customThe solvents were evaporated to dryness under reduced pressure
  2. additionthe residue was diluted to 50 ml with EtOAc
  3. washwashed with H2O
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customto give the crude product (0.63 g) as pale paste, which
  9. stirringThe mixture was stirred overnight
  10. temperatureat reflux
  11. customthe solvent was evaporated
  12. customThe residue was purified by FCC (SiO2, hexane/EtOAc)

出典と根拠

ORDレコード
ord-af12e078f3b44227b5ba6a8da60660c0
出典データセット
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08592399B2

反応ノート

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