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Cesium carbonate → N-(1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide

HRID 331061
ノート
印刷プレビュー

反応式

HRID 331061 の反応式
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:22])[C:9]([CH3:21])=[C:10]([C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][CH2:16][N:17]4[CH3:20])=[CH:13][CH:12]=3)[C:3]=12.[CH3:23][N:24]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[N:25]1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C1C=CC=CC=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>O1CCOCC1.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]>[CH3:22][N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([NH:32][S:29]([C:26]3[CH:27]=[CH:28][N:24]([CH3:23])[N:25]=3)(=[O:31])=[O:30])=[C:3]2[C:10]([C:11]2[CH:19]=[C:18]3[C:14]([CH2:15][CH2:16][N:17]3[CH3:20])=[CH:13][CH:12]=2)=[C:9]1[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 148356431-methyl-1H-pyrazole-3-sulfonamideHCID 710901424-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 71090219N-(1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-methyl-1H-pyrazole-3-sulfonamide
収率 24%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

To a solution of 4-bromo-1,2-dimethyl-3-(1-methylindolin-6-yl)-1H-pyrrolo[2,3-b]pyridine (D28) (85 mg, 0.239 mmol) in 1,4-dioxane (2 mL) was added 1-methyl-1H-pyrazole-3-sulfonamide (D94) (65.4 mg, 0.406 mmol), cesium carbonate (155 mg, 0.477 mmol), Pd2(dba)3 (16.39 mg, 0.018 mmol) and 2-(dimethylamino)-2′-(dicyclohexylphosphino)biphenyl (14.08 mg, 0.036 mmol). The reaction mixture was heated in the microwave at 150° C. for 30 mins. The reaction mixture was filtered through celite washing with ethyl acetate and the resulting solution evaporated to dryness. The residue was purified by column chromatography on silica gel, eluting with a gradient of 0-100% ethyl acetate in cyclohexane to afford a material which was further purified by MDAP (basic condition) to afford the title compound (25 mg). LCMS (A): m/z (M+H)+ 437, C22H24N6O2S requires 436 (acidic).

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthrough celite washing with ethyl acetate
  3. customthe resulting solution evaporated to dryness
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane
  6. customto afford a material which
  7. customwas further purified by MDAP (basic condition)

出典と根拠

ORDレコード
ord-4023e28a3fd3421bbe35fef28ca53e9b
出典データセット
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08877742B2

反応ノート

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