Cesium carbonate → HCID 67343119, compound

HRID 1669416Notes

Reaction equation

HRID 1669416 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)=[CH:22][C:21]=2[O:34][CH2:35][C@@H:36]2[CH2:38][O:37]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOCC>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[N:9]3[C:8]=2[C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)=[CH:22][C:21]=2[O:34][CH2:35][C@@H:36]([OH:37])[CH2:38]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86627896HCID 86627896, compound

Product 1

HCID 67343119HCID 67343119, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

Methyl 3-cyclohexyl-2-[2-[(2S)-oxiran-2-ylmethoxy]-4-(pyridin-2-ylmethoxy)phenyl]-1H-indole-6-carboxylate was dissolved in DMF (0.1 M) and the solution was added slowly to a suspension of Cs2CO3 (0.5 eq) in DMF at 65° C. After 1 h the mixture was diluted with Et2O. The solution was extracted with H2O, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo to leave an orange amorphous solid. The product was purified by FC (PE:EtOAc, 1:1+1% NEt3 to wash away remaining starting material, then EtOAc:MeOH, 9:1+1% NEt3). The product was obtained as a yellowish amorphous solid (62%). (ES+) m/z 513 (M+H)+.

Workup

  1. extractionThe solution was extracted with H2O, sat. aq. NaHCO3 and brine
  2. dry with materialAfter drying over Na2SO4 all volatiles
  3. customwere evaporated in vacuo
  4. customto leave an orange amorphous solid
  5. customThe product was purified by FC (PE
  6. washEtOAc, 1:1+1% NEt3 to wash away

Sources & evidence

ORD record
ord-0223d39a95b44d69a37999db16ca6d5d
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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