Pyridine → HCID 67393727, compound

HRID 1776937Notes

Reaction equation

HRID 1776937 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[C:27]([Br:28])=[CH:26][C:10]2[C:11]([C:21]([O:23][CH2:24][CH3:25])=[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:28][C:27]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][CH2:24][CH3:25])=[O:22])[C:10]=2[CH:26]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67393744HCID 67393744, compound

Product 1

HCID 67393727HCID 67393727, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

MsCl (31.7 g, 277.5 mmol) was added to a solution of ethyl 6-amino-5-bromo-2-(4-fluorophenyl)benzofuran-3-carboxylate (35 g, 92.5 mmol) and pyridine (60 mL) in dichloromethane (300 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 crystallized with EtOAc to provide the pure product of ethyl 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (35 g, yield: 82%). 1H-NMR (CDCl3, 400 MHz) δ 8.27 (s, 1H), 8.01˜8.05 (m, 2H), 7.87 (s, 1H), 7.15˜7.19 (m, 2H), 6.87 (s, 1H), 4.38˜4.43 (m, 2H), 3.00 (s, 3H), 1.40 (t, J=40 Hz, 3H). MS (M+H)+: 456/458.

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
  7. customusing crystallized with EtOAc

Sources & evidence

ORD record
ord-325c7ef1ac584d2d9a43d42fba0c47f4
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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