Triethylamine → [2-(5-Pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

HRID 29104

反応式

HRID 29104 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]([CH3:24])([CH3:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:4][CH:3]=1.[C:25]([C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)#[CH:26].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>[N:29]1[CH:30]=[CH:31][CH:32]=[C:27]([C:25]#[C:26][C:2]2[S:6][C:5]([C:7]3[N:8]=[C:9]4[CH:14]=[N:13][CH:12]=[CH:11][N:10]4[C:15]=3[NH:16][C:17]([CH3:24])([CH3:23])[CH2:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[CH:4][CH:3]=2)[CH:28]=1

参加物

9

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 1860033-EthynylpyridineHCID 69316811[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

生成物 1

HCID 69319991[2-(5-Pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine収率 49%

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

600 mg (1.48 mmol) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetra-methyl-butyl)-amine were dissolved together with 183 mg (1.77 mmol) of 3-ethynylpyridine, 104 mg (0.15 mmol) of bis(triphenylphosphine)-palladium(II) chloride and 28 mg (0.15 mmol) of copper(I)-iodide in DMF (10 ml). After addition of 2.00 ml (14.78 mmol) of triethylamine, the mixture was stirred at 50° C. for 3 d. 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 dried over sodium sulfate. After filtration and removal of the solvents under a vacuum, column chromatography (EA) was carried out with the group. After crystallisation of the resultant crude product, 310 mg (0.72 mmol, 49% of theoretical) of [2-(5-pyridin-3-ylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-(1,1,3,3-tetramethyl-butyl)-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
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration and removal of the solvents under a vacuum, column chromatography (EA)
  6. customAfter crystallisation of the resultant crude product

出典と根拠

ORDレコード
ord-f3e3e7e692764aa3980362c7015455e1
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

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