Acetic Acid → 5-Bromo-6-ethoxy-1,7-naphthyridin-8-amine

HRID 1881762노트

반응식

HRID 1881762 반응식
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([NH2:14])[N:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].C(O)(=O)C.[Br:19]Br.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:19][C:5]1[C:4]([O:3][CH2:1][CH3:2])=[N:13][C:12]([NH2:14])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 24408BromineHCID 516892Sodium BicarbonateHCID 130013416-Ethoxy-1,7-naphthyridin-8-amine

생성물 1

HCID 591431045-Bromo-6-ethoxy-1,7-naphthyridin-8-amine수율 65.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a 250 mL round bottom flask was added 6-ethoxy-1,7-naphthyridin-8-amine (0.65 g, 3.43 mmol), glacial acetic acid (20 mL), followed by the dropwise addition of bromine (0.60 g, 3.78 mmol) dissolved in carbontetrachloride (40 mL). After addition was complete, the mixture was stirred for 2 h then neutralized with saturated NaHCO3 and extracted with ethyl acetate. The organic layer was washed with brine, dried over Na2SO4 and concentrated. The resultant residue was purified by silica gel to yield 5-bromo-6-ethoxy-1,7-naphthyridin-8-amine as a pale yellow solid (0.6 g, 2.24 mmol, 65%). 1H NMR (400 MHz, CDCl3): δ ppm 8.53 (d, J=3.95 Hz, 1H), 8.22 (d, J=8.79 Hz, 1H), 7.50 (dd, J=8.57, 4.17 Hz, 1H), 5.87 (br. s., 2H), 4.48 (q, J=7.03 Hz, 2H), 1.44 (t, J=7.03 Hz, 3H). LC/MS m/z 270 [M+H].

후처리

  1. additionAfter addition
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resultant residue was purified by silica gel

출처 및 근거

ORD 기록
ord-94b5f109a1b6461993afaa349a8275d0
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318941B2

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