Triethylamine → N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine

HRID 29113

反応式

HRID 29113 の反応式
[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[CH:21])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[N:24]=1.CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][N:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[N:24]=2)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

9

反応物 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 6394382-Bromo-6-fluoropyridineHCID 86613493Tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine

生成物 1

HCID 11552894N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine収率 30.2%

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2 回

反応条件

温度
50 °C

実験手順

500 mg (1.69 mmol) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyrazin-3-yl]-amine (synthesis described in Example 158 part b) were dissolved together with 355 mg (2.02 mmol) of 2-bromo-6-fluoro-pyridine in DMF (20 ml). 2.4 ml (16.9 mmol) of NEt3, 32 mg (0.17 mmol) of copper(I) iodide and 119 mg (0.17 mmol) bis(triphenylphosphine)-palladium(II) chloride were added to this solution. The reaction mixture was heated to 50° C. for 6 h. The mixture was then diluted with EA and combined with a 1M aq. Na2CO3 solution. The phases were separated and the aq. phase was extracted with EA. The combined organic phases were washed with a 1M aq. Na2CO3 solution, dried over MgSO4, filtered and evaporated under a vacuum. 200 mg (0.51 mmol, 30%) of N-tert-butyl-2-(5-((6-fluoropyridin-2-yl)ethynyl)thiophen-2-yl)imidazo[1,2-a]pyrazin-3-amine were obtained by CC (EA) of the group.

後処理

  1. customThe phases were separated
  2. extractionthe aq. phase was extracted with EA
  3. washThe combined organic phases were washed with a 1M aq. Na2CO3 solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under a vacuum

出典と根拠

ORDレコード
ord-9eda6fc09d7f4466ab4ac41a09e23be2
出典データセット
uspto-grants-2008_09
特許番号
US07420056B2

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