Methylamine → 2-Methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic Acid Benzyl Ester

HRID 966530Notes

Reaction equation

HRID 966530 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][NH2:29]>C(O)C>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][NH:29][CH3:28])[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 233938525-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 99669522-Methyl-5-(2-methylamino-ethyl)-1H-indole-3-carboxylic Acid Benzyl EsterYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (500 mg, 1.29 mmol, Example 56, Step D) in 29% methylamine in ethanol solution (6 mL) was stirred at room temperature overnight and then partitioned between methylene chloride and water. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was triturated with diethyl ether to give 410 mg (99%) of the desired product as a white foam: mp 65-68° C.; MS(APCI+): m/z 323.1 (MH+); Anal. Calcd for C20H22N2O2.0.5H2O: C, 72.48; H, 7.00; N, 8.45. Found: C, 72.21; H, 6.85; N, 8.34.

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give a residue, which
  7. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-eb9a9715d109428887ee8e45d04c8a7c
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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