Pyridine → 7-Iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

HRID 1162036Notes

Reaction equation

HRID 1162036 reaction equation
[I:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11](Cl)(=[O:13])=[O:12])[CH:3]=1.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([O:23][CH3:24])=[C:20]([CH:22]=1)[NH2:21].N1C=CC=CC=1>ClCCl>[I:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([NH:21][C:20]2[CH:22]=[C:16]([CH3:15])[CH:17]=[CH:18][C:19]=2[O:23][CH3:24])(=[O:13])=[O:12])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 84452-Methoxy-5-MethylanilineHCID 534029757-Iodobenzofuran-5-sulfonyl chloride2×

Product 1

HCID 668925067-Iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-iodo-1-benzofuran-5-sulfonyl chloride (10.75 g, 31 mmol; Intermediate 56) in dichloromethane (200 mL) was added 5-methyl-2-methoxyaniline (4.25 g, 31 mmol) and pyridine (7.4 mL, 93 mmol) and allowed to stir at ambient temperature overnight. The dark red solution was washed with water, separated, dried and filtered through a plug of silica to remove most of the red impurity, and finally concentrated. Yield: 13.51 g (99%) red solid. HPLC 90% RT=2.58 min (System A; 30-80% MeCN over 3 min), 1.75 min (System C; 2-95% MeCN over 2 min). 1H NMR (400 MHz, CDCl3) δ ppm 2.23 (m, 3H) 3.52 (s, 3H) 6.54 (d, J=8.30 Hz, 1H) 6.79 (dd, J=8.42, 1.59 Hz, 1H) 6.86 (d, J=2.20 Hz, 1H) 6.96 (s, 1H) 7.31 (d, J=1.71 Hz, 1H) 7.71 (d, J=2.20 Hz, 1H) 7.95 (d, J=1.71 Hz, 1H) 8.04 (d, J=1.71 Hz, 1H). MS (ESI) for C16H14INO4S m/z 444 (M+H).

Workup

  1. washThe dark red solution was washed with water
  2. customseparated
  3. customdried
  4. filtrationfiltered through a plug of silica
  5. customto remove most of the red impurity
  6. concentrationfinally concentrated
  7. wait30-80% MeCN over 3 min), 1.75 min (System C; 2-95% MeCN over 2 min)

Sources & evidence

ORD record
ord-e9b2b14de3124c699c0a7ab785e76412
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

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