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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate

HRID 1778337
Notes
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Reaction equation

HRID 1778337 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][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1>N1C=CC=CC=1>[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][CH3:27])=[O:25])=[C:22]2[C:17]([C:18]3[CH:30]=[CH:29][O:28][C:19]=3[CH:20]=[N:21]2)=[CH:16][CH:15]=1)(=[O:11])=[O:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride2×HCID 66685912Methyl 7-aminofuro[2,3-c]quinoline-6-carboxylate2×

Product 1

HCID 66685289Methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylateYield 24.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) in pyridine (10 mL) was heated to 70° C. and a solution of methyl 7-amino-furo[2,3-c]quinoline-6-carboxylate (Intermediate 16, 0.33 g) in pyridine (10 mL) was added. The mixture was stirred and heated at 70° C. for 4 hours. Further 2-bromo-4-fluorobenzenesulfonyl chloride (0.57 g) was added and the mixture was stirred and heated at 70° C. overnight. After cooling, the mixture was filtered and the solid was washed with methanol. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%. The product was triturated with diethyl ether and the solid was collected by filtration to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-furo[2,3-c]quinoline-6-carboxylate (0.16 g) as a yellow solid.

Workup

  1. stirringthe mixture was stirred
  2. temperatureheated at 70° C. overnight
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washthe solid was washed with methanol
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica
  8. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 15-60%
  9. customThe product was triturated with diethyl ether
  10. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-5687ad9c6ba94877852d1ea388dc9d65
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09266896B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes