Cesium carbonate → N-[5-(2-fluoro-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 2100699

反応式

HRID 2100699 の反応式
I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[F:24][C:25]1[C:30](B(O)O)=[CH:29][CH:28]=[CH:27][N:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Pd].O1CCOCC1>[F:24][C:25]1[C:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[CH2:7][CH:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]3)=[CH:29][CH:28]=[CH:27][N:26]=1

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 27832702-Fluoropyridine-3-boronic acidHCID 46899809N-(5-iodo-2,3-dihydro-1H-inden-2-yl)-2-propanesulfonamide

生成物 1

HCID 11709762N-[5-(2-fluoro-3-pyridinyl)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide収率 37%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of Intermediate 2 (65 mg, 0.18 mmol) and cesium carbonate (1.5 eq, 88 mg, 0.27 mmol) in a 3:1 mixture of 1,4-dioxan:water (4 ml) was degassed with argon for 5 minutes. Then the mixture was added to (2-fluoro-3-pyridinyl)boronic acid (1.1 eq, 28 mg, 0.20 mmol, Asymchem International Inc.). Palladium acetate (2 mg, 0.01 mmol—alternatively, solid supported palladium may be used), and triphenylphosphine (9 mg, 0.03 mmol) were then added and the whole mixture stirred at reflux for 16 h. The reaction mixture was allowed to cool and partitioned between ethyl acetate (10 ml) and water (10 ml). The organic layer was separated, dried and evaporated. The resulting product was purified using mass directed preparative HPLC to give the title compound (22 mg, 37%).

後処理

  1. customwater (4 ml) was degassed with argon for 5 minutes
  2. additionwere then added
  3. temperatureat reflux for 16 h
  4. temperatureto cool
  5. custompartitioned between ethyl acetate (10 ml) and water (10 ml)
  6. customThe organic layer was separated
  7. customdried
  8. customevaporated
  9. customThe resulting product was purified

出典と根拠

ORDレコード
ord-6e6c4d9543bf4da5846922de8f093690
出典データセット
uspto-grants-2009_08
特許番号
US07572819B2

関連ノート

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