propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate → Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate

HRID 476226

Reaction equation

HRID 476226 reaction equation
[N+](=[CH:3][C:4](=[O:23])[CH2:5][CH2:6][C:7]1[NH:8][C:9]2[C:14]([C:15]=1[CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N-]>C([O-])(=O)CCCCCCC.[Rh+2].C([O-])(=O)CCCCCCC.C(Cl)Cl>[O:23]=[C:4]1[CH2:3][N:8]2[C:9]3[C:14]([C:15]([CH2:16][C:17]([O:19][CH2:20][CH2:21][CH3:22])=[O:18])=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3

Participants

4

Reactant 1

HCID 86655415propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate

Product 1

HCID 58399159Propyl (7-oxo-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetateYield 64%

Reagents, catalysts & solvents 2

HCID 10178397Rhodium(II) octanoateCatalystHCID 6344DichloromethaneSolvent

Procedure

Rhodium (II) octanoate dimmer (0.1 equiv.) was added to a CH2Cl2 solution (0.02 M) of propyl [2-(4-diazo-3-oxobutyl)-1H-indol-3-yl]acetate from Step 4. The reaction mixture was stirred overnight at rt and then concentrated. The residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO) eluting with EtOAc/Hexane (2:98 to 10:90) to give the title compound (64%) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by column chromatography on silica gel using automatized gradiant pump system CombiFlashRF (Teledyne ISCO)
  3. washeluting with EtOAc/Hexane (2:98 to 10:90)

Sources & evidence

ORD record
ord-a20c9f11ee5d46ecafec9752809a5003
Source dataset
uspto-grants-2014_01
Patent number
US08637671B2

Linked notes

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