Iodine → (4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester

HRID 723108

반응식

HRID 723108 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:14])[CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CNCCN(C)C.C([Li])CCC.[I:28]I>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:14])[C:13]=1[I:28])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 807IodineHCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 21300389HCID 21300389, 화합물HCID 178418339Butyllithium

생성물 1

HCID 60026355(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester수율 14%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

(5-Methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (255 mg, 1.2 mmol, Example 139: step a) and trimethylethylenediamine (905 μL, 6.0 mmol) were dissolved into THF (4 mL) and cooled to −78° C. To this was added n-Butyllithium (2.5M, 2.4 mL, 6.0 mmol). The reaction was stirred at −78° C. for 30 minutes and then warmed to RT for 30 minutes. Iodine (1.5 g, 6.0 mmol) was dissolved into THF (4 mL) and added to the reaction mixture at −78° C. slowly. The reaction was warmed to RT for 1 hour and the solvents were removed in vacuo. The residue was dissolved into EtOAc and washed with brine and water. The combined organic layers were dried (MgSO4) and solvents were removed in vacuo followed by purification by flash column chromatography (SiO2) (50% EtOAc in hexanes) that yielded the title compound as a yellow solid (55 mg, 14%). 1H-NMR (CDCl3): δ 8.91 (s, 1H), 8.07 (s, 1H), 6.81 (br s, 1H), 2.44 (s, 3H), 1.56 (s, 9H). ESI-MS (m/z): Calcd. for C11H15IN2O2: 335.0 (M+1); found: 334.9.

후처리

  1. temperaturewarmed to RT for 30 minutes
  2. additionadded to the reaction mixture at −78° C. slowly
  3. temperatureThe reaction was warmed to RT for 1 hour
  4. customthe solvents were removed in vacuo
  5. dissolutionThe residue was dissolved into EtOAc
  6. washwashed with brine and water
  7. dry with materialThe combined organic layers were dried (MgSO4) and solvents
  8. customwere removed in vacuo
  9. customfollowed by purification by flash column chromatography (SiO2) (50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-3d19d1ec471649208030a0b37969a852
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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