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2-Bromo-4-fluorobenzene-1-sulfonyl chloride → methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715954
Notes
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Reaction equation

HRID 715954 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[CH:5][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15].[Br:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[S:26](Cl)(=[O:28])=[O:27]>N1C=CC=CC=1.C(Cl)Cl.C(OCC)(=O)C>[Br:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[S:26]([NH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][CH2:13][C:6]3=[CH:5][C:4]=2[C:3]=1[C:14]([O:16][CH3:17])=[O:15])(=[O:28])=[O:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 27782162-Bromo-4-fluorobenzene-1-sulfonyl chlorideHCID 86712114methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2×

Product 1

HCID 70984190methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylateYield 57.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 18, 0.300 g) and 2-bromo-4-fluorobenzenesulfonyl chloride (0.427 g) in pyridine (4 mL) and DCM (12 mL) was stirred at room temperature for 30 minutes. The resultant mixture was diluted with ethyl acetate and washed with aqueous potassium carbonate solution (10%) and brine. The organic layer was dried (MgSO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica, eluting with a mixture of methanol and DCM with a gradient of 0-2% to give methyl 7-(2-bromo-4-fluorobenzenesulfonylamino]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.350 g) as a white foam.

Workup

  1. washwashed with aqueous potassium carbonate solution (10%) and brine
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by chromatography on silica
  6. washeluting with a mixture of methanol and DCM with a gradient of 0-2%

Sources & evidence

ORD record
ord-e0f95ff4f32748d1b080749324e43240
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09187494B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes