Benzenesulfonyl chloride → HCID 49758931、化合物

HRID 1020906ノート

反応式

HRID 1020906 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][N:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][N:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 2

HCID 7369Benzenesulfonyl chlorideHCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridine

生成物 1

HCID 49758931HCID 49758931、化合物収率 73.9%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a mixture of 4-methoxy-7-azaindole (6.4 g, 43.2 mmol) in dichloromethane (200 mL) and 50% aqueous sodium hydroxide (200 mL) was added benzenesulfonyl chloride (6.1 mL, 47.5 mmol) and tetrabutylammonium bromide (1.4 g, 4.3 mmol). The mixture was stirred vigorously at room temperature for 18 hours. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was recrystallized from ethyl acetate and hexanes to give 9.2 g of 1-benzenesulfonyl-4-methoxy-7-azaindole as a yellow solid. 1H NMR (DMSO-d6) δ 8.30 (d, J=5 Hz, 1H), 8.18 (d, 1 Hz, 1H), 7.58 (m, 2H), 7.47 (m, 2H), 6.67 (d, 4 Hz, 1H), 6.61 (d, 4 Hz, 1H), 3.94 (s, 3H). MS (m/z) 289 (M+H).

後処理

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from ethyl acetate and hexanes

出典と根拠

ORDレコード
ord-5038c587efa045b88c5723d41efc326f
出典データセット
uspto-grants-2014_05
特許番号
US08716493B2

反応ノート

読み込み中…