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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate

HRID 595120
Notes
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Reaction equation

HRID 595120 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]3[CH:12]=[CH:13][N:14]=[C:7]3[CH2:6][O:5][C:4]=2[C:3]=1[C:15]([O:17][CH3:18])=[O:16].[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1.C(Cl)Cl>[Br:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[S:27]([NH:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]3[CH:12]=[CH:13][N:14]=[C:7]3[CH2:6][O:5][C:4]=2[C:3]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:29])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chloride2×HCID 86712824methyl 7-amino-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate2×

Product 1

HCID 70983693methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylateYield 80.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent

Procedure

A mixture of methyl 7-amino-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate (Intermediate 26, 0.379 g) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.466 g) in pyridine (10 mL) and DCM (10 mL) was stirred at room temperature for 17 hours. A further amount of 2-bromo-4-fluorobenzenesulfonyl chloride (0.190 g) was added and the mixture was stirred at room temperature for 5 hours. The resultant mixture was concentrated in vacuo and the residue was dissolved in DCM and water and passed through a phase separator. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with ethyl acetate to give a white solid which was triturated with ether to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino)-4H-5-oxa-3,9b-diazacyclopenta[a]naphthalene-6-carboxylate (0.603 g) as an off-white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 5 hours
  2. concentrationThe resultant mixture was concentrated in vacuo
  3. dissolutionthe residue was dissolved in DCM
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica
  6. washeluting with ethyl acetate
  7. customto give a white solid which
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-debba7d723ce4c44bf68db8943fbc1ea
Source dataset
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09242997B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes