Pyridine → HCID 11314988, compound

HRID 1766284Notes

Reaction equation

HRID 1766284 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.[CH3:19][O:20][C:21]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][C:26]=2[CH:27]=1)=[O:22].C([O-])(O)=O.[Na+]>ClCCl>[CH3:19][O:20][C:21]([C:23]1[O:24][C:25]2[CH:31]=[CH:30][C:29]([NH:32][S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=3[CH3:12])(=[O:10])=[O:9])=[CH:28][C:26]=2[CH:27]=1)=[O:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 5227343-Chloro-2-methylbenzenesulfonyl chlorideHCID 10845388Methyl 5-aminobenzofuran-2-carboxylate

Product 1

HCID 11314988HCID 11314988, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-2-methylbenzenesulphonyl chloride (99 mg, 0.44 mmol) in dichloromethane (3 mL) was added pyridine (85 μL, 1.05 mmol) and the mixture was stirred under N2 for 5 min, after which time 5-amino-benzofuran-2-carboxylic acid methyl ester (80 mg, 0.42 mmol) was added. The resulting mixture was stirred for 2 h at room temperature, then saturated NaHCO3 solution (10 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 an off-white solid (122 mg, 77%), single spot at Rf 0.47 (2:1 hexane:ethyl acetate). mp 139.4-140.1° C., HPLC purity 99+% (tR 1.90 min in 10% water-acetonitrile). 1H NMR (CDCl3): δ 7.83 (1H, d, J=7.9 Hz), 7.55 (1H, d, J=7.9 Hz), 7.44 (1H, d, J=9.0 Hz), 7.42 (1H, s), 7.39 (1H, d, J=2.2 Hz), 7.17 (1H, t, J=8.0 Hz), 7.05 (1H, dd, J8.7, 2.2 Hz), 6.65 (1H, s, N—H), 3.95 (3H, s), 2.72 (3H, s). LCMS: 378.16. FAB-MS (MH+, C17H14ClNO5S): calcd 379.0281, found 379.0281.

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-74fa08342bce435caca367847e32c235
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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