Sodium Carbonate → 4-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide

HRID 2035543ノート

反応式

HRID 2035543 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([NH2:11])=[O:10])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[C:16]([F:21])[CH:15]=2)[CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([N:32]2[C:36]3=[N:37][CH:38]=[CH:39][CH:40]=[C:35]3[C:34](B(O)O)=[CH:33]2)(=[O:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[C:18]([F:20])[CH:17]=1)[CH2:13][NH:12][C:4]1[CH:3]=[C:2]([C:34]2[C:35]3[C:36](=[N:37][CH:38]=[CH:39][CH:40]=3)[N:32]([S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[CH:33]=2)[N:7]=[CH:6][C:5]=1[CH2:8][C:9]([NH2:11])=[O:10]

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 45789698(1-Tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)boronic acidHCID 1317309496-Chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide

生成物 1

HCID 1317310074-[(3,5-difluorobenzyl)amino]-6-{1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyridine-3-carboxyamide収率 54.7%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

26 mg of 6-chloro-4-[(3,5-difluorobenzyl)amino]pyridine-3-carboxyamide (the compound of Example 20) was dissolved in 0.5 mL of tetrahydrofuran, to which 33 mg of 1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-3-boronic acid, 10 mg of tetrakis(triphenylphosphine) palladium (0), and 0.5 mL of 2 mol/L sodium carbonate in water were added, and stirred at 80° C. for 14 hours. To the reaction mixture, water was added, extracted with chloroform, the extract was washed with water, and dried on anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1) to obtain 25 mg (yield 54%) of the title compound as a white solid.

後処理

  1. additionwere added
  2. extractionextracted with chloroform
  3. washthe extract was washed with water
  4. dry with materialdried on anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel thin layer chromatography (chloroform:methanol=20:1)

出典と根拠

ORDレコード
ord-cf4a1ccf73414186a43bb6aad5e9020d
出典データセット
uspto-grants-2013_11
特許番号
US08575153B2

反応ノート

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