Triethylamine → (6-Bromo-3-nitro-pyridin-2-yl)-(2-chloro-pyridin-4-yl)-amine

HRID 1524195노트

반응식

HRID 1524195 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.Br[C:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([Br:19])[N:11]=1.C(N(CC)CC)C>CC(O)C>[Br:19][C:12]1[N:11]=[C:10]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[CH:7]=2)[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 844322-Chloropyridin-4-amineHCID 5550532,6-Dibromo-3-nitropyridine

생성물 1

HCID 86651872(6-Bromo-3-nitro-pyridin-2-yl)-(2-chloro-pyridin-4-yl)-amine

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

2-Chloro-pyridin-4-ylamine (1 eq, 6.6 mmol, 850 mg) and 2,6-dibromo-3-nitro pyridine (2 eq, 13.2 mmol, 3.85 g) are dissolved in IPA (15 ml) and heated using microwave radiation at 150° C. for 6 hours. After cooling to room temperature, triethylamine (1 eq) is added and reaction mixture is stirred for 1 hour. The majority of solvent is removed in vacuo and the residue is diluted using 6% DCM in iso-hexane (75 ml). The solvent is decanted off and the process repeated 3 times. The resulting brown solid is dissolved in DCM and excess amine is scavenged using SCX-2 resin (6 g) and discarded. The solid is triturated in hexane, DCM and IPA (50 ml of a 58:40:2 mixture) and the resulting yellow solid is collected by filtration. The solid is dissolved in DCM and washed with water. The organic portion is dried (MgSO4) and concentrated in vacuo to afford the title compound; [M+H]+ 330.

후처리

  1. temperatureheated
  2. customat 150° C.
  3. customfor 6 hours
  4. customreaction mixture
  5. customThe majority of solvent is removed in vacuo
  6. additionthe residue is diluted
  7. customThe solvent is decanted off
  8. dissolutionThe resulting brown solid is dissolved in DCM
  9. customThe solid is triturated in hexane
  10. filtrationDCM and IPA (50 ml of a 58:40:2 mixture) and the resulting yellow solid is collected by filtration
  11. dissolutionThe solid is dissolved in DCM
  12. washwashed with water
  13. dry with materialThe organic portion is dried (MgSO4)
  14. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f657d07850114f42acd4fbaeb8c0ed68
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079897B2

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