Ethylenediamine → N-(6-Methoxy-2-methyl-3-pyridyl)ethane-1,2-diamine

HRID 631797노트

반응식

HRID 631797 반응식
Br[C:2]1[C:3]([CH3:10])=[N:4][C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[CH2:11]([NH2:14])[CH2:12][NH2:13].CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C(OC)=CC=C(OC)C=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[CH3:9][O:8][C:5]1[N:4]=[C:3]([CH3:10])[C:2]([NH:13][CH2:12][CH2:11][NH2:14])=[CH:7][CH:6]=1

참가 물질

7

반응물 3

HCID 3301EthylenediamineHCID 107981463-Bromo-6-methoxy-2-methylpyridineHCID 23676156Sodium t-butoxide

생성물 1

HCID 89825702N-(6-Methoxy-2-methyl-3-pyridyl)ethane-1,2-diamine수율 78.1%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 25112535Brettphos촉매HCID 312751,4-Dioxane용매

실험 절차

3-Bromo-6-methoxy-2-methylpyridine (50 mg, 0.247 mmol), ethane-1,2-diamine (0.083 ml, 1.237 mmol), sodium tert-butoxide (47.6 mg, 0.495 mmol) and dicyclohexyl-[3,6-dimethoxy-2-(2,4,6-thisopropylphenyl)phenyl]phosphane (6.64 mg, 0.012 mmol) were dissolved under argon in anhydrous 1,4-dioxane (2.5 ml). Next, Pd2(DBA)3 (11.33 mg, 0.012 mmol) was added and the mixture was heated in a sealed flask to 70 C overnight. The reaction mixture was filtered over kieselguhr, rinsed with EtOAc and the combined filtrates were concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, gradient of 0.5% to 10% of [7N NH3 in MeOH] in DCM to yield 35 mg (0.193 mmol, 78%) of a yellow oil. MS(ESI) m/z=182.2 [M+1]+.

후처리

  1. temperaturethe mixture was heated in a sealed flask to 70 C overnight
  2. filtrationThe reaction mixture was filtered over kieselguhr
  3. washrinsed with EtOAc
  4. concentrationthe combined filtrates were concentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica, gradient of 0.5% to 10% of [7N NH3 in MeOH] in DCM

출처 및 근거

ORD 기록
ord-d5e22886585b46a39544a71a49e0a03f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321724B2

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