Trimethylsilyldiazomethane → methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylate

HRID 1444626Notes

Reaction equation

HRID 1444626 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[Br:8][C:9]1[N:10]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])[C:11]2[C:16]([C:17]=1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[CH:15][CH:14]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:12]=2>C1(C)C=CC=CC=1.CO>[Br:8][C:9]1[N:10]([CH2:28][CH2:29][C:30]([O:32][CH3:1])=[O:31])[C:11]2[C:16]([C:17]=1[CH:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)=[CH:15][CH:14]=[C:13]([C:24]([O:26][CH3:27])=[O:25])[CH:12]=2

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 685061433-[2-bromo-3-cyclohexyl-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid

Product 1

HCID 68501826methyl 2-bromo-3-cyclohexyl-1-(3-methoxy-3-oxopropyl)-1H-indole-6-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 21867641Toluene methanolSolvent

Procedure

1.6 eq of (Trimethylsilyl)diazomethane (2 M solution in hexanes) was added dropwise to a solution of 3-[2-bromo-3-cyclohexyl-6-(methoxycarbonyl)-1H-indol-1-yl]propanoic acid in a mixture toluene:MeOH (7:3; 0.2 M) and the solution allowed to stir at RT for 1 h. Excess (Trimethylsilyl)diazomethane was quenched with acetic acid and then the solution was concentrated in vacuo. The crude was purified by flash chromatography (Biotage cartridge Si4OS, 1:9 EtOAc/PE) to afford the title compound in 63% yield (over two steps). MS (ES+) m/z 422 (M+H)+, m/z 424 (M+H)+

Workup

  1. customExcess (Trimethylsilyl)diazomethane was quenched with acetic acid
  2. concentrationthe solution was concentrated in vacuo
  3. customThe crude was purified by flash chromatography (Biotage cartridge Si4OS, 1:9 EtOAc/PE)

Sources & evidence

ORD record
ord-29c79cf4539e4936ad9426ff4a374f1a
Source dataset
uspto-grants-2010_02
Patent number
US07662809B2

Reaction notes

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