Diisopropylethylamine → HCID 59850172、化合物

HRID 2064170ノート

反応式

HRID 2064170 の反応式
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[C:12]([F:15])([F:14])[F:13].C(N(C(C)C)CC)(C)C.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1>CN(C)C=O>[Br:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]2)[CH:7]=1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 594197851-Bromo-5-fluoro-4-nitro-2-(trifluoromethyl)benzene

生成物 1

HCID 59850172HCID 59850172、化合物収率 58%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A stirred solution of 2-bromo-4-fluoro-5-nitrobenzotrifluoride (1.15 g, 4.0 mmol) in dimethylformamide (15 ml) at room temperature under argon was treated with diisopropylethylamine (1.8 ml, 10 mmol) and 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (0.90 g, 4.5 mmol), then heated at 75° C. for 3 hrs. The solution was concentrated under vacuum and the residue treated with 10% Na2CO3 solution (30 ml) and extracted with ethyl acetate (2×40 ml). The combined extract was washed with brine (40 ml), then dried (Na2SO4) and concentrated under vacuum to leave an orange solid which was purified by chromatography on silica gel (20 g) eluting with dichloromethane to afford the title compound as a yellow solid (1.08 g, 58%).

後処理

  1. concentrationThe solution was concentrated under vacuum
  2. additionthe residue treated with 10% Na2CO3 solution (30 ml)
  3. extractionextracted with ethyl acetate (2×40 ml)
  4. extractionThe combined extract
  5. washwas washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under vacuum
  8. customto leave an orange solid which
  9. customwas purified by chromatography on silica gel (20 g)
  10. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-41831bf277764772a9ac91ebaec1e9bd
出典データセット
uspto-grants-2012_10
特許番号
US08288412B2

反応ノート

読み込み中…