Sodium Carbonate → Tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

HRID 29111

반응식

HRID 29111 반응식
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[S:12][C:11]([C:13]2[N:14]=[C:15]3[CH:20]=[N:19][CH:18]=[CH:17][N:16]3[C:21]=2[NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:10][CH:9]=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCN(CC)CC.CC(=O)OCC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:23]([NH:22][C:21]1[N:16]2[CH:17]=[CH:18][N:19]=[CH:20][C:15]2=[N:14][C:13]=1[C:11]1[S:12][C:8]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])=[CH:9][CH:10]=1)([CH3:26])([CH3:24])[CH3:25]

참가 물질

9

반응물 3

HCID 10340Sodium CarbonateHCID 66111TrimethylsilylacetyleneHCID 69317100[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine

생성물 1

HCID 69322358Tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine수율 65.1%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

21.4 ml (155 mmol) of trimethylsilylacetylene, 2.4 g (12.9 mmol) of copper(I) iodide and 4.5 g (6.5 mmol) of bis(triphenylphosphine)-palladium(II) chloride were added to a solution of 45.3 g (129 mmol) of [2-(5-bromo-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine (synthesis described in Example 18, part a) in DMF (760 ml) and NEt3 (90 ml). The reaction solution was heated to 60° C. for 4 h and stirred at RT for 16 h. The mixture was then combined with a 1M aq. Na2CO3 solution and diluted with EA. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with water and dried over MgSO4. After filtration and removal of the solvents under a vacuum, the resultant group was redissolved with an EA/DCM (1:1) mixture and filtered through diatomaceous earth. The filtrate was evaporated under a vacuum. 30.8 g (84 mmol, 65%) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained from the group were by crystallisation from tert.-butyl-methyl ether.

후처리

  1. customsynthesis
  2. customThe phases were separated
  3. extractionthe aq. phase was extracted with EA
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationAfter filtration and removal of the solvents under a vacuum
  7. dissolutionthe resultant group was redissolved with an EA/DCM (1:1) mixture
  8. filtrationfiltered through diatomaceous earth
  9. customThe filtrate was evaporated under a vacuum

출처 및 근거

ORD 기록
ord-dfed8011b29e499095d725e08842eacf
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07420056B2

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