Cesium carbonate → 6-Pyridin-3-yl-5-pyridin-4-yl-N-1,3-thiazol-2-ylpyrazin-2-amine

HRID 1710709노트

반응식

HRID 1710709 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[N:9][C:8]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:2]=1.Br[C:21]1[S:22][CH:23]=[CH:24][N:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]=[C:11]([NH:13][C:21]3[S:22][CH:23]=[CH:24][N:25]=3)[CH:10]=[N:9][C:8]=2[C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)[CH:2]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 16071665HCID 16071665, 화합물

생성물 1

HCID 594575686-Pyridin-3-yl-5-pyridin-4-yl-N-1,3-thiazol-2-ylpyrazin-2-amine수율 44%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

실험 절차

An oven dried resealable Schlenk tube was charged with 6-pyridin-3-yl-5-pyridin-4-ylpyrazin-2-amine (Example 13, 60 mg, 0.241 mmol), 2-bromo-1,3-thiazole (22 μL, 0.241 mmol), cesium carbonate (110 mg, 0.337 mmol) and dioxane (2.5 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (9 mg, 0.01 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (11 mg, 0.019 mmol) was added. After three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in a 100° C. oil bath. After 16 h, the mixture was cooled, partitioned between water and ethyl acetate, the aqueous phase was extracted twice with ethyl acetate, the organic layers washed with brine, dried (MgSO4) and evaporated. Flash chromatography (95:5 dichloromethane/methanol) furnished the title compound as a solid (35 mg, 44%).

후처리

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three new cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in a 100° C.
  5. temperaturethe mixture was cooled
  6. custompartitioned between water and ethyl acetate
  7. extractionthe aqueous phase was extracted twice with ethyl acetate
  8. washthe organic layers washed with brine
  9. dry with materialdried (MgSO4)
  10. customevaporated

출처 및 근거

ORD 기록
ord-1d219bb66e734daaaa4422d076d7db08
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790728B2

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