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

HRID 1180571ノート

反応式

HRID 1180571 の反応式
[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]

参加物

6

反応物 5

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a5fe6721cafd407ba80ebd8bdc039810
出典データセット
uspto-grants-2007_10
特許番号
US07282506B2

反応ノート

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