1,8-Diazabicyclo(5.4.0)undec-7-ene → N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide

HRID 43028

反応式

HRID 43028 の反応式
[CH3:1][CH:2]([S:4](Cl)(=[O:6])=[O:5])[CH3:3].[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH2:18])[CH2:13][CH2:12]2.N12CCCN=C1CCCCC2>C(Cl)Cl>[Br:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[CH:14]([NH:18][S:4]([CH:2]([CH3:3])[CH3:1])(=[O:6])=[O:5])[CH2:13][CH2:12]2

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 222283885-bromo-2,3-dihydro-1H-inden-1-amine

生成物 1

HCID 66733842N-(5-bromo-2,3-dihydro-1H-inden-1-yl)propane-2-sulfonamide収率 31.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

At 0° C. and under protective atmosphere, a solution of 2-propanesulfonyl chloride (11.87 mL, 121 mmol) in DCM (121 mL) was added gradually to a solution of 5-bromo-2,3-dihydro-1H-inden-1-amine (12.8 g, 60.4 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (4.83 mL, 32.1 mmol) in dichloromethane (300 mL). The reaction was stirred at rt overnight. The reaction mixture was washed with 1N KHSO4 (1×) and sat NaHCO3 (2×) before being dried on Na2SO4 and solvent evaporated in vacuo to afford a green oil. Purification by column chromatography (25% EtOAc in hept) afforded the title compound as a white solid (6.0 g, 18.9 mmol, 31%). MS (ESI): m/z [M−H]− 317.0.

後処理

  1. washThe reaction mixture was washed with 1N KHSO4 (1×)
  2. custombefore being dried on Na2SO4 and solvent
  3. customevaporated in vacuo
  4. customto afford a green oil
  5. customPurification by column chromatography (25% EtOAc in hept)

出典と根拠

ORDレコード
ord-9635bdb015714342a19415cc7011a04d
出典データセット
uspto-grants-2013_09
特許番号
US08536214B2

関連ノート

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