Sodium Bicarbonate → N-Phenyl-N'-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}urea

HRID 28869ノート

反応式

HRID 28869 の反応式
Br[C:2]1[C:3]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:21])=[CH:15][CH:14]=2)=[N:4][N:5]([CH2:7][CH:8]2[CH2:12][CH2:11][CH2:10][O:9]2)[CH:6]=1.C1(S([N:38]2[C:42]3=[N:43][CH:44]=[CH:45][C:46](B4OC(C)(C)C(C)(C)O4)=[C:41]3[CH:40]=[CH:39]2)(=O)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C)C=O>[C:23]1([NH:22][C:20]([NH:19][C:16]2[CH:17]=[CH:18][C:13]([C:3]3[C:2]([C:46]4[CH:45]=[CH:44][N:43]=[C:42]5[NH:38][CH:39]=[CH:40][C:41]=45)=[CH:6][N:5]([CH2:7][CH:8]4[CH2:12][CH2:11][CH2:10][O:9]4)[N:4]=3)=[CH:14][CH:15]=2)=[O:21])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 450745461-(Benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridineHCID 68996099HCID 68996099、化合物

生成物 1

HCID 57398440N-Phenyl-N'-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}urea収率 11%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of N-{4-[4-bromo-1-(tetrahydro-2-furanylmethyl)-1H-pyrazol-3-yl]phenyl}-N′-phenylurea (0.147 mmol), 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (0.162 mmol), N,N-dimethylformamide (1.5 mL), saturated aqueous sodium bicarbonate (0.44 mL) and tetrakis(triphenylphosphine)palladium(0) (0.007 mmol) in a sealed tube was stirred at 100° C. for 18 hrs. The solution was cooled to room temperature, filtered though Celite and concentrated in vacuo. The residue was dissolved in methanol (5 mL) and 6.0N aqueous sodium hydroxide (1 mL) and stirred at 70° C. for 6 h. The reaction mixture was concentrated in vacuo, dissolved in water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC afforded the title compound as a white solid (11%). ESMS [M+H]+: 479.4

後処理

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered though Celite
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in methanol (5 mL)
  5. stirring6.0N aqueous sodium hydroxide (1 mL) and stirred at 70° C. for 6 h
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. dissolutiondissolved in water (10 mL)
  8. extractionextracted with ethyl acetate (3×10 mL)
  9. dry with materialThe combined organic extracts were dried over magnesium sulfate
  10. concentrationconcentrated in vacuo
  11. customPurification of the residue by Gilson reverse phase HPLC

出典と根拠

ORDレコード
ord-1b8937e3c4f4463fa81a8e0fb0119e00
出典データセット
uspto-grants-2008_09
特許番号
US07419988B2

反応ノート

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