Trifluoroacetic acid → (4-Chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine

HRID 1754727노트

반응식

HRID 1754727 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[N:6][C:7]=1F.[Cl:18]C1C=CC(C=O)=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:5]2[CH:4]=[CH:3][CH:2]=[C:7]([Cl:18])[N:6]=2)=[CH:12][CH:13]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 77264-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 57619198(5-Bromo-6-fluoro-pyridin-2-yl)-(4-chloro-benzyl)-amine

생성물 1

HCID 57619237(4-Chloro-benzyl)-(6-chloro-pyridin-2-yl)-amine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To 6-chloro-pyridin-2-ylamine (537, 5.60 g, 0.0436 mol) in acetonitrile (300 mL) were added 4-chlorobenzaldehyde (40, 6.7 g, 0.048 mol), trifluoroacetic acid (13 mL, 0.17 mol) and triethylsilane (21 mL, 0.13 mol). The reaction was heated to reflux for 4 hours, then concentrated, poured into water, extracted with ethyl acetate, and washed with sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The filtrate was purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give a white solid (538, 6.5 g, 59%). MS (ESI) [M+H+]+=255.1.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. washwashed with sodium bicarbonate and brine
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe filtrate was purified with silica gel column chromatography
  11. washeluting with 20% to 100% ethyl acetate in hexane
  12. customto give a white solid (538, 6.5 g, 59%)

출처 및 근거

ORD 기록
ord-d10c52c06a5140548e5114c7aff14bc1
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169250B2

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