Potassium Carbonate → 3-Chloro-N-[2-(4-isoquinolinyl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573655

反応式

HRID 573655 の反応式
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[CH3:23].[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.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>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[CH:24]=[N:25][CH:26]=4)=[C:3]([CH3:23])[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 3761204Isoquinoline-4-boronic acidHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

生成物 1

HCID 683239073-Chloro-N-[2-(4-isoquinolinyl)-3,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide収率 37.2%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 77) (100 mg, 0.232 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added 4-isoquinolinylboronic acid (40.1 mg, 0.232 mmol), bis(triphenylphosphine)palladium(II) chloride (16.26 mg, 0.023 mmol) and potassium carbonate (112 mg, 0.811 mmol) and the mixture heated at 100° C. for 1 h using a microwave reactor. The mixture was then filtered through celite, washing with ethyl acetate (30 mL) and the filtrate evaporated to dryness. The residue was then purified by MDAP (acidic conditions), to afford the title compound (41.45 mg). LCMS (A) m/z: 480 [M+1]+, Rt 1.13 min (acidic).

後処理

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with ethyl acetate (30 mL)
  3. customthe filtrate evaporated to dryness
  4. customThe residue was then purified by MDAP (acidic conditions)

出典と根拠

ORDレコード
ord-df96f4948d40466e8266fbf0709b341c
出典データセット
uspto-grants-2015_05
特許番号
US09029545B2

関連ノート

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