Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | HCID 86627895 | HCID 86627895 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67343224 | HCID 67343224 | 49% |
Reaction Steps
Methyl 3-cyclohexyl-2-(2-(methoxymethoxy)-4-{[(4-methylphenyl)sulfonyl]oxy}-phenyl)-1H-indole-6-carboxylate was suspended in MeOH 0.18 M) and NaOMe (5 eq) was added. The mixture was warmed in a closed vessel to 80° C. After 4 h additional NaOMe (5 eq) was added. The mixture was warmed overnight. The mixture was cooled to RT and 1N aqueous HCl was added to the mixture. After dilution with H2O the mixture was extracted with EtOAc. The organic phase was separated and washed with sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The residual material was filtered with PE:EtOAc (8:2) through a pad of silica gel. The product was obtained as a yellowish amorphous solid (49%). (ES+) m/z 410 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07989438B2 |
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| Source dataset | uspto-grants-2011_08 |
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| ORD ID | ord-8b43a9f7d2d64634b101d98226fe029a |
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| Source note | uspto-grants-2011_08 |
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