HCID 10269137, compound → HCID 60037060, compound

HRID 966518Notes

Reaction equation

HRID 966518 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][CH2:22][N:23]([CH3:25])[CH3:24])[CH:18]=2)[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17](/[CH:20]=[CH:21]\[CH2:22][N:23]([CH3:25])[CH3:24])[CH:18]=2)[NH:13][C:12]=1[CH3:26])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 10269137HCID 10269137, compound

Product 1

HCID 60037060HCID 60037060, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

5-(3-Dimethylamino-prop-1-ynyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (0.160 g, 0.428 mmol, 1 eq, Example 53) was dissolved in ethanol (30 mL). Lindlar's catalyst (0.05 mg) was added, and the reaction was hydrogenated at room temperature under a hydrogen atmosphere, 35 PSI. The reaction mixture was shaken at room temperature and followed by LC-MS. After one week, the reaction was loaded on silica gel and chromatographed, (ethyl acetate/methanol/triethylamine 87/10/3). The resulting indole-alkene product (0.019 g, 12%) was converted to the —HCl salt, obtained as a brown semisolid: LC/MS (ESI+) 377 (M+1), Anal. (C24H28N2O2.HCl.1.0H2O) C, H, N.

Workup

  1. customwas hydrogenated at room temperature under a hydrogen atmosphere
  2. waitAfter one week
  3. customchromatographed
  4. customobtained as a brown semisolid

Sources & evidence

ORD record
ord-602e2872a2d54c8fbd0070a82e5e086a
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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