Methyl chloroformate → methyl 7-{N-[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate

HRID 1778407Notes

Reaction equation

HRID 1778407 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([NH:14][C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)(=[O:13])=[O:12].Cl[C:33]([O:35][CH3:36])=[O:34].C(=O)(O)[O-].[Na+]>C1COCC1>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[S:11]([N:14]([C:15]1[C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:23]2[C:18]([C:19]3[CH:31]=[CH:30][O:29][C:20]=3[CH2:21][O:22]2)=[CH:17][CH:16]=1)[C:33]([O:35][CH3:36])=[O:34])(=[O:12])=[O:13]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 66685486methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate2×

Product 1

HCID 66685495methyl 7-{N-[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% dispersion in oil, 0.043 g) in THF (10 mL) was added methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-furo[2,3-c]chromene-6-carboxylate (Intermediate 7, 0.40 g). Once gas evolution had ceased, methyl chloroformate (0.102 mL) was added and the resultant mixture was stirred at room temperature for 2.5 hours. Saturated aqueous sodium bicarbonate solution was added and the mixture was extracted with ethyl acetate. The combined organic layers were dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was triturated with ether to give methyl 7-{N[2-bromo-4-fluorobenzenesulfonyl]-N-(methoxycarbonyl)amino}-4H-furo[2,3-c]chromene-6-carboxylate (0.230 g) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-44d3ed9f12da43d19fd802dbc75d2e97
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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