Sodium Methoxide → HCID 68508583, compound

HRID 1714020Notes

Reaction equation

HRID 1714020 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]([CH2:29][C:30](OC)=[O:31])[C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:13]=2.C[O-].[Na+]>CO.CCOC(C)=O>[CH:19]1([C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:25]([O:27][CH3:28])=[O:26])=[CH:13][C:12]=3[N:11]3[CH2:29][C:30](=[O:31])[NH:1][CH2:2][C:3]4[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=4[C:10]=23)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 68506958HCID 68506958, compound

Product 1

HCID 68508583HCID 68508583, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-[2-(aminomethyl)-4-fluorophenyl]-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate (1 eq., from Step 3) in dry MeOH (0.05 M), 10% in weight of sodium methoxide was added and the mixture stirred at RT overnight. The volume of the solution was reduced in vacuo, before diluting with EtOAc. The organic phase was washed with HCl 1 N and brine, before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was used in the next step without further purification (83%); MS (ES+) m/z 421 (M+H)+.

Workup

  1. washThe organic phase was washed with HCl 1 N and brine
  2. dry with materialbefore being dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-5a8d81be00164fa69e70ceec6792be91
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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