Formic Acid → 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole

HRID 715936Notes

Reaction equation

HRID 715936 reaction equation
[C:1]1([S:7]([NH:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][CH2:22][C:15]4=[CH:14][C:13]=3[C:12]=2C(OC)=O)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].C(O)=O>O1CCOCC1.O.CO>[C:1]1([S:7]([NH:10][C:11]2[CH:19]=[CH:18][C:17]3[N:16]4[CH2:20][CH2:21][CH2:22][C:15]4=[CH:14][C:13]=3[CH:12]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 284Formic AcidHCID 3939Lithium HydroxideHCID 70983444methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate2×

Product 1

HCID 709841467-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indoleYield 36.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole-8-carboxylate (Intermediate 26, 0.075 g) and lithium hydroxide mononhydrate (0.049 g) in dioxane (2 mL) and water (1 mL) was irradiated in the microwave at 110° C. for 20 minutes. After cooling, the mixture was diluted with water and acidified to pH4-5 with formic acid. The resultant solid was washed with water and ether, then dried to give a cream powder. The solid was dissolved in methanol and acetone and freeze-dried, then dried in a dessicator, in vacuo, at 40° C. overnight. The solid was triturated with DCM and filtered, washed with DCM (1 mL) and pentane (1 mL) then dried in a dessicator, in vacuo, at 40° C. overnight. The yellow solid was dissolved in hot ethyl acetate and pentane was added until the mixture went cloudy. On cooling, the solid was collected by filtration, washed with pentane and dried in a dessicator, in vacuo, at 40° C. overnight to give 7-benzenesulfonylamino-2,3-dihydro-1H-pyrrolo[1,2-a]indole (0.023 g) as a cream solid.

Workup

  1. temperatureAfter cooling
  2. washThe resultant solid was washed with water and ether
  3. customdried
  4. customto give a cream powder
  5. dry with materialacetone and freeze-dried
  6. customdried in a dessicator, in vacuo, at 40° C. overnight
  7. customThe solid was triturated with DCM
  8. filtrationfiltered
  9. washwashed with DCM (1 mL) and pentane (1 mL)
  10. customthen dried in a dessicator, in vacuo, at 40° C. overnight
  11. dissolutionThe yellow solid was dissolved in hot ethyl acetate
  12. additionpentane was added until the mixture
  13. temperatureOn cooling
  14. filtrationthe solid was collected by filtration
  15. washwashed with pentane
  16. customdried in a dessicator, in vacuo, at 40° C. overnight

Sources & evidence

ORD record
ord-f43db273792f4642be99538b3d8de42e
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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