Triethylamine → 1-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

HRID 1357261Notes

Reaction equation

HRID 1357261 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C:17](Cl)=[O:18])=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][NH:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[CH:29]=[C:28]([OH:33])[CH:27]=[CH:26]2.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[OH:33][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([CH2:22][N:21]([CH3:20])[C:17]([C:10]1[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:9]=1)=[O:18])[CH:32]=[CH:31]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 104922281-benzylindole-3-carbonyl ChlorideHCID 185052756-Methylaminomethyl-naphthalen-2-ol

Product 1

HCID 865873871-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amideYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-Benzyl-1H-indole-3-carbonyl chloride, prepared in the previous step, in 50 mL of anhydrous THF was added dropwise under nitrogen over 2 h to a mixture of 6-methylaminomethyl-naphthalen-2-ol (2.5 g, 13.37 mmol), prepared in step 1 of Example 32, and triethylamine (1.86 mL, 13.37 mmol) in 300 mL of anhydrous THF at room temperature. The reaction stirred for 17.5 h (overnight). A trace amount of solid was removed by filtration and the filtrate was concentrated under reduced pressure to give a brown oil. The oil was diluted with ethyl acetate, extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 1-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (5.83 g, 100%) as a brown foam, MS m/z: 421 [M+H]+.

Workup

  1. customA trace amount of solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto give a brown oil
  4. extractionextracted two times with 1N HCl
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-35c8ab755c9c41fa9269c6bed90162e5
Source dataset
uspto-grants-2003_07
Patent number
US06589970B2

Reaction notes

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