tert-Butanol → (8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester

HRID 1180571노트

반응식

HRID 1180571 반응식
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](C(O)=O)[CH:8]=[CH:7]2.C([N:17]([CH2:20]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.CCOC(C)=O.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46]>>[C:45]([O:49][C:20](=[O:29])[NH:17][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=2)[N:10]=1)([CH3:48])([CH3:47])[CH3:46]

참가 물질

6

반응물 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 27610508-bromo-1,6-naphthyridine-2-carboxylic Acid

생성물 1

HCID 58979577(8-Bromo-[1,6]naphthyridin-2-yl)-carbamic acid tert-butyl ester

실험 절차

8-Bromo-[1,6]naphthyridine-2-carboxylic acid (1 equiv.) is suspended in tert-butanol (20 mL). Triethylamine (1.1 equiv.) and diphenylphosphoryl azide (1.1 equiv.) are added and the reaction is warmed to reflux. After refluxing for 2.5 hours, the reaction is allowed to cool and half the solvent is removed by rotary evaporation. The residue is dissolved in ethyl acetate (200 mL) and washed with saturated NaHCO3 (50 mL). The organic phase is dried over magnesium sulfate, filtered and concentrated to afford the crude product. Silica gel chromatography (1:1 EtOAc:hexanes) affords the desired BOC amine as a solid, LC/MS (M+H) 324.1.

후처리

  1. temperaturethe reaction is warmed to reflux
  2. temperatureAfter refluxing for 2.5 hours
  3. temperatureto cool
  4. customhalf the solvent is removed by rotary evaporation
  5. dissolutionThe residue is dissolved in ethyl acetate (200 mL)
  6. washwashed with saturated NaHCO3 (50 mL)
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford the crude product

출처 및 근거

ORD 기록
ord-a5fe6721cafd407ba80ebd8bdc039810
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07282506B2

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