Benzenesulfonyl chloride → HCID 59812105、化合物

HRID 2114057ノート

反応式

HRID 2114057 の反応式
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][CH:3]=1.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[O-]S(O)(=O)=O.C(Cl)Cl>[C:13]1([S:19]([N:4]2[C:5]3=[N:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=[C:10]3[C:2]([I:1])=[CH:3]2)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 242292213-Iodo-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

生成物 1

HCID 59812105HCID 59812105、化合物収率 75.2%

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of iodide 36 (3.50 g, 13.0 mmol), PhSO2Cl (2.49 mL, 19.5 mmol), n-Bu4NHSO4 (0.57 g, 1.69 mmol) in CH2Cl2 (77 mL) was treated with 50% aq. NaOH (2.46 mL) then stirred for 40 min. It was then poured onto water (250 mL), the aqueous phase extracted with more CH2Cl2 (3×60 mL) and the combined organic extracts dried (MgSO4) and concentrated. Methanol was added to the resulting solid and the mixture stirred for 0.5 h. The solid was filtered off and washed with more methanol (2×) to afford iodide 37 as a white solid (4.00 g, 75%); 1H NMR (400 MHz, CDCl3) δ 7.46 (t, J=5.7 Hz, 2H), 7.59 (tt, J=7.5, 2.0 Hz, 1H), 7.93 (d, J=1.9 Hz, 1H), 7.95 (s, 1H), 8.16 (m, 2H), 8.60 (d, J=2.0 Hz, 1H).

後処理

  1. additionIt was then poured onto water (250 mL)
  2. extractionthe aqueous phase extracted with more CH2Cl2 (3×60 mL)
  3. dry with materialthe combined organic extracts dried (MgSO4)
  4. concentrationconcentrated
  5. additionMethanol was added to the resulting solid
  6. stirringthe mixture stirred for 0.5 h
  7. filtrationThe solid was filtered off
  8. washwashed with more methanol (2×)

出典と根拠

ORDレコード
ord-29c035d2ff4f43aebe89835f59f25b7e
出典データセット
uspto-grants-2008_10
特許番号
US07432375B2

反応ノート

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