Triethylamine → Ethyl (E)-3-(4-Amino-6-bromo-3-pyridyl)acrylate

HRID 523080노트

반응식

HRID 523080 반응식
[NH2:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([Br:9])[CH:3]=1.[C:10]([O:14][CH2:15][CH3:16])(=[O:13])[CH:11]=[CH2:12].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[NH2:1][C:2]1[CH:3]=[C:4]([Br:9])[N:5]=[CH:6][C:7]=1/[CH:12]=[CH:11]/[C:10]([O:14][CH2:15][CH3:16])=[O:13]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 601457042-Bromo-5-iodopyridin-4-amine

생성물 1

HCID 89995588Ethyl (E)-3-(4-Amino-6-bromo-3-pyridyl)acrylate수율 89.6%

시약·촉매·용매 3

HCID 80271Tri-o-tolylphosphine촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

4-Amino-2-bromo-5-iodopyridine (9.0 g 30.0 mmole) was dissolved in DMF (90 mL) and ethyl acrylate (6.5 mL, 60 mmole), triethylamine (6.1 mL, 43.2 mmole), tri-o-tolylphosphine (728 mg 2.4 mmole) and palladium acetate (270 mg 1.2 mmole) were added. The reaction was placed under nitrogen and heated at 100° C. for 3 hours. The reaction was concentrated in vacuo and diluted with EtOAc (250 mL). Water (100 mL) was added and the biphasic mixture filtered through celite. The filter cake was washed with EtOAc and the organic layers collected. The combined organic layers were washed with water (2×100 mL), brine, dried over sodium sulphate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with a gradient of 10-40% EtOAc in DCM to afford the title compound (7.29 g, 89%).

후처리

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with EtOAc (250 mL)
  3. additionWater (100 mL) was added
  4. filtrationthe biphasic mixture filtered through celite
  5. washThe filter cake was washed with EtOAc
  6. customthe organic layers collected
  7. washThe combined organic layers were washed with water (2×100 mL), brine
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified
  11. washeluting with a gradient of 10-40% EtOAc in DCM

출처 및 근거

ORD 기록
ord-80b24a51172c4ff59352cb27ca2abd1c
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334286B2

반응 노트

불러오는 중…