Pyridine → HCID 66686135, compound

HRID 1778379Notes

Reaction equation

HRID 1778379 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[C:22]2[C:17]([C:18]3[CH:34]=[CH:33][O:32][C:19]=3[C:20](=[O:31])[O:21]2)=[CH:16][CH:15]=1.N1C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:13][C:14]1[C:23]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])=[C:22]2[C:17]([C:18]3[CH:34]=[CH:33][O:32][C:19]=3[C:20](=[O:31])[O:21]2)=[CH:16][CH:15]=1)(=[O:11])=[O:10]

Participants

5

Reactant 3

HCID 1049PyridineHCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride2×HCID 66685765HCID 66685765, compound2×

Product 1

HCID 66686135HCID 66686135, compoundYield 87.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-fluorobenzenesulfonyl chloride (0.229 g) was added to a solution of tert-butyl 7-amino-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 57, 0.210 g) and pyridine (1.13 mL) in DCM (20 mL) and the mixture was stirred at room temperature overnight. The mixture was reduced to half volume in vacuo and the resultant mixture was stirred and heated at 35° C. for 6 hours. Further 2-bromo-4-fluorobenzenesulfonyl chloride (0.572 g) was added and the reaction mixture was heated at 35° C. overnight. The mixture was evaporated to dryness and the residue was partitioned between water and ethyl acetate. The combined organic layers were dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with ethyl acetate and cyclohexane, with a gradient of 5-20% to give tert-butyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4-oxo-4H-furo[2,3-c]chromene-6-carboxylate (0.329 g) as a white solid.

Workup

  1. temperatureheated at 35° C. for 6 hours
  2. temperaturethe reaction mixture was heated at 35° C. overnight
  3. customThe mixture was evaporated to dryness
  4. customthe residue was partitioned between water and ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customThe residue was purified by chromatography on silica
  9. washeluting with ethyl acetate and cyclohexane, with a gradient of 5-20%

Sources & evidence

ORD record
ord-30d6462a0f2844f3b58433469bcb1543
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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