HCID 59259249, compound → HCID 19696439, compound

HRID 475480Notes

Reaction equation

HRID 475480 reaction equation
[N:1]([CH:4]1[CH2:16][N:8]2[C:9]3[C:14]([CH:15]=[C:7]2[CH2:6][CH2:5]1)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[N+]=[N-]>CO.[Pd]>[CH:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[CH:15]=[C:7]1[CH2:6][CH2:5][CH:4]([NH2:1])[CH2:16][N:8]12

Participants

4

Reactant 1

HCID 59259249HCID 59259249, compound

Product 1

HCID 19696439HCID 19696439, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (+/−) 7-azido-6,7,8,9-tetrahydropyrido[1,2-α]indole from Step 8 in MeOH (0.1 M) was added 10% palladium on carbon (200 mg per g of substrate). The reaction mixture was flushed a few times with hydrogen and then stirred overnight at rt under a 1 atmosphere pressure of hydrogen. The reaction mixture was diluted with CH2Cl2 and was filtered through Celite, the cake was washed with EtOAc and the filtrate concentrated under vacuum. The residue was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:0:0 to 89:10:01) to give the title compound (81%) as a brown gum.

Workup

  1. customThe reaction mixture was flushed a few times with hydrogen
  2. additionThe reaction mixture was diluted with CH2Cl2
  3. filtrationwas filtered through Celite
  4. washthe cake was washed with EtOAc
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe residue was purified by column chromatography on silica gel eluting with CH2Cl2/MeOH/NH4OH (100:0:0 to 89:10:01)

Sources & evidence

ORD record
ord-4b564937fbbb4549aacdaefa813c4de7
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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