Benzenesulfonyl chloride → methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate

HRID 715962Notes

Reaction equation

HRID 715962 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:11][C:12]1[CH:20]=[CH:19][C:18]2[N:17]3[CH2:21][CH2:22][CH2:23][C:16]3=[CH:15][C:14]=2[C:13]=1[C:24]([O:26][CH3:27])=[O:25]>C(Cl)Cl.N1C=CC=CC=1.C(OCC)(=O)C>[C:1]1([S:7]([NH:11][C:12]2[CH:20]=[CH:19][C:18]3[N:17]4[CH2:21][CH2:22][CH2:23][C:16]4=[CH:15][C:14]=3[C:13]=2[C:24]([O:26][CH3:27])=[O:25])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 86712114methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2×

Product 1

HCID 70983444methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylateYield 48.5%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzenesulfonyl chloride (0.092 g) was added to a solution of methyl 7-amino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 18, 0.100 g) in DCM (4 mL) and pyridine (1 mL) and the resultant mixture was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and washed with aqueous potassium carbonate solution, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo, then dissolved in toluene and re-evaporated to dryness. The residue was purified by chromatography on silica, eluting with a mixture of ammonia in methanol (2M) and DCM, with a gradient of 0-2%. The resultant solid was triturated with diethyl ether to give methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (0.078 g) as a cream powder.

Workup

  1. washwashed with aqueous potassium carbonate solution
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in toluene
  6. customre-evaporated to dryness
  7. customThe residue was purified by chromatography on silica
  8. washeluting with a mixture of ammonia in methanol (2M) and DCM, with a gradient of 0-2%
  9. customThe resultant solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-df5e3a0032f941f38578e9aa178d67f4
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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