Benzenesulfonyl chloride → HCID 59812105, compound

HRID 2114057Notes

Reaction equation

HRID 2114057 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 59812105HCID 59812105, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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×)

Sources & evidence

ORD record
ord-29c035d2ff4f43aebe89835f59f25b7e
Source dataset
uspto-grants-2008_10
Patent number
US07432375B2

Reaction notes

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