Triethylamine → Tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

HRID 29097

反応式

HRID 29097 の反応式
Br[C:2]1[S:6][C:5]([C:7]2[N:8]=[C:9]3[CH:14]=[N:13][CH:12]=[CH:11][N:10]3[C:15]=2[NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:4][CH:3]=1.[C:21]1([C:27]#[CH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.CC(=O)OCC.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.[Cu]I>[C:17]([NH:16][C:15]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:5]1[S:6][C:2]([C:28]#[C:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:3][CH:4]=1)([CH3:20])([CH3:19])[CH3:18]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 10821PhenylacetyleneHCID 69317100[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine

生成物 1

HCID 11530854Tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine収率 73.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

420 mg (1.2 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-tert-butyl-amine were dissolved together with 0.33 ml (3.0 mmol) of phenylacetylene, 42 mg (0.06 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 22 mg (0.12 mmol) of copper(I) iodide in DMF (9 ml). After addition of 1.6 ml (12.0 mmol) of triethylamine, the mixture was stirred at 50° C. for 16 h. The reaction solution was then diluted with EA and combined with a sat. aq. sodium carbonate solution. The phases were separated and the aqueous phase extracted with EA. The combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution and dried over magnesium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA/DCM 1:4) was carried out with the group, after which 326 mg (0.88 mmol, 73% of theoretical) of tert-butyl-[2-(5-phenylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine were obtained.

後処理

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with EA
  3. washThe combined organic phases were washed 2× with a sat. aq. sodium carbonate solution and 2× with a sat. aq. common salt solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration and removal of the solvents under a vacuum, column chromatography (EA/DCM 1:4)

出典と根拠

ORDレコード
ord-0708f3b4a08648e1a55002a67bb78689
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

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