Diisopropylethylamine → HCID 59850172, 화합물

HRID 2064170노트

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HRID 2064170 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 59850172HCID 59850172, 화합물수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-41831bf277764772a9ac91ebaec1e9bd
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288412B2

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