Pyridine → HCID 67393054, compound

HRID 1776907Notes

Reaction equation

HRID 1776907 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:26]([Br:27])=[CH:25][C:10]2[C:11]([C:21]([O:23][CH3:24])=[O:22])=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[O:13][C:9]=2[CH:8]=1.N1C=CC=CC=1>ClCCl.O>[Br:27][C:26]1[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[C:11]([C:21]([O:23][CH3:24])=[O:22])[C:10]=2[CH:25]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67393637HCID 67393637, compound

Product 1

HCID 67393054HCID 67393054, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

MsCl (4.8 g, 41.2 mmol) was added to a solution of methyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate (5.0 g, 13.4 mmol) and pyridine (5.4 g, 68.7 mL) in dry dichloromethane (50 mL) at 0° C. After stirred overnight at room temperature, the mixture was diluted with water, and extracted with dichloromethane. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified using column chromatography to provide methyl 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (5.3 g, yield: 83%). 1H-NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.99˜8.03 (m, 2H), 7.83 (s, 1H), 7.11˜7.16 (m, 2H), 6.82 (br s, 1H), 3.90 (s, 3H), 2.96 (s, 3H). MS (M+H)+: 442/444.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

Sources & evidence

ORD record
ord-5bb63bc566bf4921b3c12050f05da47d
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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