HCID 58767566, compound → HCID 58767572, compound

HRID 1748253Notes

Reaction equation

HRID 1748253 reaction equation
[C:1]([C:3]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:13]=2)[CH:8]=[C:7]1[C:20]([O:22]CC)=O)([CH3:5])[CH3:4])#[N:2]>[Ni].O>[CH3:4][C:3]1([CH3:5])[N:6]2[C:14]3[CH:13]=[C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:11]=[CH:10][C:9]=3[CH:8]=[C:7]2[C:20](=[O:22])[NH:2][CH2:1]1

Participants

4

Reactant 1

HCID 58767566HCID 58767566, compound

Product 1

HCID 58767572HCID 58767572, compoundYield 115.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of diethyl 1-(2-cyanopropan-2-yl)-1H-indole-2,6-dicarboxylate (9.3 g, 23.3 mmol) and Raney Ni (4 g of 50% wet catalyst) and water (5 mL) water is heated to 50° C. under 250 psi of H2. The mixture is stirred for 18 h. LCMS shows complete reaction with high purity. The mixture is filtered through Celite, keeping the catalyst wet until properly disposed. The solvent was removed under reduced pressure to afford the title compound (7.7 g, 95%) as a white solid.

Workup

  1. customreaction with high purity
  2. filtrationThe mixture is filtered through Celite
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-55a5efc84a8544aca4fd0d4b5695b9a0
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

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