2,3-Dihydro-1H-pyrrolo[1,2-a]indol-1-one → HCID 19889894, compound

HRID 653685Notes

Reaction equation

HRID 653685 reaction equation
[C:1]1(=[O:13])[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2]1.[CH3:14][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1(C)C=CC=CC=1>[OH:13][C:1]1([CH3:14])[C:5]2=[CH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[N:4]2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 105590922,3-Dihydro-1H-pyrrolo[1,2-a]indol-1-oneHCID 22635083Tetrahydrofuran tolueneHCID 178418573HCID 178418573, compound

Product 1

HCID 19889894HCID 19889894, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-one (613 mg, 3.58 mmol) suspended in toluene (12 mL), at 0° C. there was added methyl magnesium bromide 1.5M in toluene/THF (75:25) (3.0 mL, 4.5 mmol). The mixture was stirred at 0° for 5 minutes, then at room temperature for 20 minutes. After quenching with saturated aqueous NH4Cl solution, the mixture was partitioned between H2O and EtOAc. The crude product obtained from the organic fraction was chromatographed on a column of silica gel eluting with a 1:2 mixture of EtOAc and hexane to afford the title product as a yellow oil.

Workup

  1. waitat room temperature for 20 minutes
  2. customAfter quenching with saturated aqueous NH4Cl solution
  3. customthe mixture was partitioned between H2O and EtOAc
  4. customThe crude product obtained from the organic fraction
  5. customwas chromatographed on a column of silica gel eluting with a 1:2 mixture of EtOAc and hexane

Sources & evidence

ORD record
ord-877d7a5baaa5408b97f41cf82bf9c593
Source dataset
uspto-grants-1992_07
Patent number
US05128364

Reaction notes

Loading…