2-Bromo-4-fluorobenzene-1-sulfonyl chloride → HCID 66685755, compound

HRID 1778402Notes

Reaction equation

HRID 1778402 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:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH2:24])[CH:17]=[CH:16][C:15]=1[C:25]1[CH:29]=[CH:28][O:27][C:26]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[NH2:13][C:14]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([NH:24][S:9]([C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Br:1])(=[O:11])=[O:10])[CH:17]=[CH:16][C:15]=1[C:25]1[CH:29]=[CH:28][O:27][C:26]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

5

Reactant 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride3×HCID 666854812-Furancarboxylic acid, 3-[2,4-diamino-3-(methoxycarbonyl)phenyl]-, ethyl ester2×

Product 1

HCID 66685755HCID 66685755, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-fluorobenzenesulfonyl chloride (0.584 g) was added to a solution of ethyl 3-(2,4-diamino-3-methoxycarbonylphenyl)-furan-2-carboxylate (Intermediate 89, 0.650 g) in DCM (30 mL) and pyridine (10 mL). The resultant mixture was stirred at room temperature for 45 minutes. A further amount of 2-bromo-4-fluorobenzene-sulfonyl chloride (0.584 g) was added and the mixture stirred for a further 1 hour. A further amount of 2-bromo-4-fluorobenzenesulfonyl chloride (0.300 g) was added and the mixture stirred for a further 30 minutes. The mixture was concentrated in vacuo and the residue was partitioned between water and DCM. The organic layer was dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was triturated with methanol and the resultant solid was collected by filtration and air dried to give ethyl 3-[2-amino-4-(2-bromo-4-fluorobenzenesulfonylamino)-3-methoxycarbonylphenyl]-furan-2-carboxylate (0.960 g) as a powder.

Workup

  1. stirringthe mixture stirred for a further 30 minutes
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between water and DCM
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was triturated with methanol
  8. filtrationthe resultant solid was collected by filtration and air
  9. customdried

Sources & evidence

ORD record
ord-e4d3c2ad457545b38b76b2634a8eb6bc
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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