Pyridine → HCID 11393526, compound

HRID 1766283Notes

Reaction equation

HRID 1766283 reaction equation
[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8](Cl)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[NH2:19][C:20]1[CH:21]=[CH:22][C:23]2[O:27][CH:26]=[C:25]([CH3:28])[C:24]=2[CH:29]=1.C([O-])(O)=O.[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([CH3:12])=[C:4]([S:8]([NH:19][C:20]2[CH:21]=[CH:22][C:23]3[O:27][CH:26]=[C:25]([CH3:28])[C:24]=3[CH:29]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 20824567HCID 20824567, compound

Product 1

HCID 11393526HCID 11393526, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (128 mg, 0.571 mmol) in dichloromethane (3 mL) was added pyridine (110 μL, 1.36 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-3-methyl-benzofuran (80 mg, 0.54 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (8 mL) was added and the mixture was extracted into ethyl acetate (15 mL). The organic phase was washed with brine, dried (Na2SO4), filtered and evaporated to give a residue that was purified using flash chromatography to afford a yellow solid (159 mg, 87%), single spot at Rf 0.65 (2:1 hexane:ethyl acetate). mp 119.5-120.1° C., HPLC purity 99% (tR 2.22 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.82 (1H, d, J=7.9 Hz), 7.54 (1H, d, J=7.9 Hz), 7.38 (1H s), 7.28-7.22 (2H, m), 7.15 (1H, t, J=8.0 Hz), 6.83 (1H, dd, J=8.7, 2.2 Hz), 6.56 (1H, s, N—H, 2.72 (3H, s), 2.15 (3H, s). LCMS: 334.07 (M−). FAB-MS (MH+, C16H14ClNO3S): calcd 335.0383, found 335.0383.

Workup

  1. stirringThe resulting mixture was stirred for 2 h at room temperature
  2. extractionthe mixture was extracted into ethyl acetate (15 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a residue that
  8. customwas purified

Sources & evidence

ORD record
ord-5983a5f7aefb4d8a87c0ef0d5aa37d25
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

Loading…