Benzenesulfonyl chloride → HCID 59812105, 화합물

HRID 2114057노트

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HRID 2114057 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 59812105HCID 59812105, 화합물수율 75.2%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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×)

출처 및 근거

ORD 기록
ord-29c035d2ff4f43aebe89835f59f25b7e
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432375B2

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