HCID 71281757, compound → HCID 71281824, compound

HRID 1481722Notes

Reaction equation

HRID 1481722 reaction equation
[CH2:1]([C:3]1[C:4]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[C:19]([CH:25]2[CH2:30][N:29]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:28][CH2:27][N:26]2C(OCC2C=CC=CC=2)=O)=[CH:18]3)=[N:5][C:6]([O:13][CH3:14])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:8]=1)[CH3:2]>CO.[Pd]>[CH2:1]([C:3]1[C:4]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH3:24])[C:19]([CH:25]2[NH:26][CH2:27][CH2:28][N:29]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:30]2)=[CH:18]3)=[N:5][C:6]([O:13][CH3:14])=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:8]=1)[CH3:2]

Participants

4

Reactant 1

HCID 71281757HCID 71281757, compound

Product 1

HCID 71281824HCID 71281824, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Solution of 1-benzyl 4-tert-butyl 2-(5-(3-ethyl-6-methoxy-5-(methoxycarbonyl)pyridin-2-yl)-1-methyl-1H-indol-2-yl)piperazine-1,4-dicarboxylate (71.4 mg, 0.11 mmol), prepared according to procedure described in Example 67, Step 3, in MeOH (1 mL) was hydrogenated over Pd/C (10% Degussa type, 10 mg) with H2-balloon. After 1 h complete consumption of starting material was observed. Catalyst was filtered and washed with MeOH (5 mL). Concentration of mother liquor afforded tert-butyl 3-(5-(3-ethyl-6-methoxy-5-(methoxycarbonyl)pyridin-2-yl)-1-methyl-1H-indol-2-yl)piperazine-1-carboxylate which was used directly in the next step. LC-MS 509.3 [M+H]+, RT 1.28 min.

Workup

  1. customAfter 1 h complete consumption of starting material
  2. filtrationCatalyst was filtered
  3. washwashed with MeOH (5 mL)

Sources & evidence

ORD record
ord-91812fead42e49229427243386788226
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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