HCID 15063398, compound → HCID 15063399, compound

HRID 475478Notes

Reaction equation

HRID 475478 reaction equation
[O:1]=[C:2]1[CH:14](C(OC(C)(C)C)=O)[N:6]2[C:7]3[C:12]([CH:13]=[C:5]2[CH2:4][CH2:3]1)=[CH:11][CH:10]=[CH:9][CH:8]=3>C1(C)C=CC=CC=1>[CH:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH:13]=[C:5]1[CH2:4][CH2:3][C:2](=[O:1])[CH2:14][N:6]12

Participants

3

Reactant 1

HCID 15063398HCID 15063398, compound

Product 1

HCID 15063399HCID 15063399, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the crude tert-butyl 7-oxo-6,7,8,9-tetrahydropyrido[1,2-α]indole-6-carboxylate from Step 5 in toluene (0.06 M) was treated with silica gel (5 g per g of substrate) and the mixture was heated to reflux for 6 h. After cooling, the mixture was filtered, the cake washed with EtOAc and the combined organics were concentrated under vacuum to give the crude title compound (82%) as a brown solid. This material was used in the next step without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. washthe cake washed with EtOAc
  6. concentrationthe combined organics were concentrated under vacuum

Sources & evidence

ORD record
ord-277c0e06a2334191b24bf14096d60049
Source dataset
uspto-grants-2014_01
Patent number
US08637541B2

Reaction notes

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