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

HRID 631797ノート

反応式

HRID 631797 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 25112535Brettphos触媒HCID 312751,4-Dioxane溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-d5e22886585b46a39544a71a49e0a03f
出典データセット
uspto-grants-2016_04
特許番号
US09321724B2

反応ノート

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