Pyridine → HCID 67210939, compound

HRID 705381Notes

Reaction equation

HRID 705381 reaction equation
[NH2:1][C:2]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:5]2[C:6]([C:16]([O:18][CH3:19])=[O:17])=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.C(OCC)(=O)C.Cl>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:5]=3[C:6]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67353900HCID 67353900, compound

Product 1

HCID 67210939HCID 67210939, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 6-amino-2-(4-fluorophenyl)-5-isopropoxybenzofuran-3-carboxylate (0.6 g, 1.75 mmol) was dissolved in dichloromethane. Pyridine (0.71 mL, 8.74 mmol) and methanesulfonyl chloride (0.27 mL, 3.5 mmol) were added and the resulting yellow orange solution was stirred at room temperature 15 hours. The solvent was removed in vacuo leaving an oily residue. The oil was redissolved in 100 mL ethyl acetate and 25 mL 10% aqueous HCl. The layers were separated and the organic layer was washed with 10% aqueous sodium bicarbonate and 10% aqueous sodium chloride, dried over anhydrous sodium sulfate(s), filtered and the solvent was removed in vacuo leaving an off-white solid, 0.65 g, 88%.

Workup

  1. customThe solvent was removed in vacuo
  2. customleaving an oily residue
  3. customThe layers were separated
  4. washthe organic layer was washed with 10% aqueous sodium bicarbonate and 10% aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate(s)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customleaving an off-white solid, 0.65 g, 88%

Sources & evidence

ORD record
ord-9b39966ecfde4ce9a03565762a8d7e8f
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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