Pyridine → 1-Propanesulfonamide, N-[3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-

HRID 60084

反応式

HRID 60084 の反応式
[NH2:1][C:2]1[C:3]([F:21])=[C:4]([C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[C:17]([Br:20])[CH:18]=3)[NH:13][CH:12]=2)=[O:10])[C:5]([F:8])=[CH:6][CH:7]=1.ClCCl.N1C=CC=CC=1.[CH2:31]([S:34](Cl)(=[O:36])=[O:35])[CH2:32][CH3:33]>O>[Br:20][C:17]1[CH:18]=[C:19]2[C:11]([C:9]([C:4]3[C:3]([F:21])=[C:2]([NH:1][S:34]([CH2:31][CH2:32][CH3:33])(=[O:36])=[O:35])[CH:7]=[CH:6][C:5]=3[F:8])=[O:10])=[CH:12][NH:13][C:14]2=[N:15][CH:16]=1

参加物

6

反応物 4

HCID 1049Pyridine2 回HCID 6344DichloromethaneHCID 662791-Propanesulfonyl chloride2 回HCID 58368727(3-Amino-2,6-difluorophenyl)(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)methanone

生成物 1

HCID 119845561-Propanesulfonamide, N-[3-[(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)carbonyl]-2,4-difluorophenyl]-収率 50%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Into a reaction flask under nitrogen, (3-amino-2,6-difluoro-phenyl)-(5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone (7, 13.00 g, 36.9 mmol) is combined with 150 mL of dichloromethane and anhydrous pyridine (5.84 g, 73.8 mmol), and propane-1-sulfonyl chloride (8, 6.05 g, 42.5 mmol) is added. The reaction is stirred at room temperature overnight, and additional pyridine (1.46 g, 18.5 mmol) and propane-1-sulfonyl chloride (1.51 g, 10.6 mmol) are added. The reaction is stirred at room temperature another 3 hours, then diluted with 500 mL of water and extracted 3×250 mL with dichloromethane. The organic layers are combined and washed with 250 mL of brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material is purified by silica gel column chromatography, eluting with a gradient of ethyl acetate:hexane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (9, 8.41 g, 50%).

後処理

  1. additionis added
  2. stirringThe reaction is stirred at room temperature another 3 hours
  3. extractionextracted 3×250 mL with dichloromethane
  4. washwashed with 250 mL of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material is purified by silica gel column chromatography
  9. washeluting with a gradient of ethyl acetate
  10. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-4caf914248cd4248a5cff86edd2d7c76
出典データセット
uspto-grants-2016_09
特許番号
US09440969B2

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