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

HRID 2035543노트

반응식

HRID 2035543 반응식
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]

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-cf4a1ccf73414186a43bb6aad5e9020d
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575153B2

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