Sodium Chloride → N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine

HRID 1025643노트

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HRID 1025643 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH2:25].CC(C)([O-])C.[Na+].[Na+].[Cl-]>CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.C1(C)C=CC=CC=1>[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24][NH:25][C:2]1[N:7]=[C:6]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:5]2=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 5234Sodium ChlorideHCID 66053N,N-DimethylethylenediamineHCID 23676156Sodium t-butoxideHCID 580876901H-Pyrrolo[2,3-b]pyridine, 6-bromo-1-[tris(1-methylethyl)silyl]-

생성물 1

HCID 71008471N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine수율 56%

시약·촉매·용매 2

HCID 178418851HCID 178418851, 화합물촉매HCID 1140Toluene용매

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온도
80 °C

실험 절차

In a 25 mL round-bottomed flask, 6-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (713 mg, 2.02 mmol, Eq: 1.00), N,N-dimethylethylenediamine (1.07 g, 1.32 ml, 12.1 mmol, Eq: 6) and bis(tri-tert-butylphosphine)palladium(0) (206 mg, 404 μmol, Eq: 0.2) were combined with toluene (2 ml) to give a yellow solution. Sodium tert-butoxide (582 mg, 6.05 mmol, Eq: 3) was added. The reaction mixture was heated to 80° C. and stirred for 1 h, then poured into 20 mL sat NaCl and extracted with EtOAc (3×20 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (silica gel, 12 g, 2% to 5% MeOH in DCM) to give N1,N1-dimethyl-N2-(1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-yl)ethane-1,2-diamine (405 mg, 56%) as yellow oil that solidified upon standing.

후처리

  1. customto give a yellow solution
  2. additionpoured into 20 mL
  3. extractionextracted with EtOAc (3×20 mL)
  4. dry with materialThe organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (silica gel, 12 g, 2% to 5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-01e1cba6899b4996a033dce7a64995e3
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729078B2

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