Hydrochloric Acid → 2,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide

HRID 38829

反応式

HRID 38829 の反応式
[CH3:1][O:2][C:3]1[C:8]([NH2:9])=[CH:7][C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:5][N:4]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28].Cl.C(Cl)Cl>N1C=CC=CC=1>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:9][C:8]1[C:3]([O:2][CH3:1])=[N:4][CH:5]=[C:6]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)[CH:7]=1)(=[O:29])=[O:28]

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 6344DichloromethaneHCID 27342732,4-Difluorobenzenesulfonyl ChlorideHCID 595579202-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-amine

生成物 1

HCID 595647052,4-difluoro-N-(2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)benzenesulfonamide収率 84.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒2 回

実験手順

To a stirred solution of 2-(methyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-pyridinamine (3 g, 12.00 mmol) in pyridine (12 ml), 2,4-difluorobenzenesulfonyl chloride (1.774 ml, 13.19 mmol) was added and the reaction mixture stirred at room temperature for 2 hours. 2 N HCl (aq) solution (20 ml) and DCM (20 ml) were added and the layers separated. The aqueous layer was washed with additional DCM (2×15 ml). Then the organic layers were combined, dried (hydrophobic frit) and evaporated in vacuo to give a brown oil. There was still some pyridine in the reaction mixture so 2M HCl was added and 15 ml DCM to extract one more time. The solvent was removed in vacuo to give the title compound as an orange solid (4.3 g).

後処理

  1. customthe layers separated
  2. washThe aqueous layer was washed with additional DCM (2×15 ml)
  3. customdried (hydrophobic frit)
  4. customevaporated in vacuo
  5. customto give a brown oil
  6. additionwas added
  7. extraction15 ml DCM to extract one more time
  8. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-154cddf52c6a442d976543b54ff3ef1e
出典データセット
uspto-grants-2013_09
特許番号
US08524751B2

関連ノート

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