Cesium carbonate → HCID 67343530, compound

HRID 1669414Notes

Reaction equation

HRID 1669414 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]([OH:26])=[CH:22][C:21]=2[O:27][CH2:28][O:29][CH3:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=1>CN(C=O)C.CCOC(C)=O>[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][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=3)=[CH:22][C:21]=2[O:27][CH2:28][O:29][CH3:30])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 5642092-(Bromomethyl)pyridineHCID 67343224HCID 67343224, compound

Product 1

HCID 67343530HCID 67343530, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-cyclohexyl-2-[4-hydroxy-2-(methoxymethoxy)phenyl]-1H-indole-6-carboxylate was dissolved in DMF (0.17 M) and Cs2CO3 (1.05 eq) was added. The mixture was stirred for 20 min, then 2-bromomethylpyridine (1.05 eq) was added and the suspension was stirred at RT. After 4 h Cs2CO3 (0.3 eq) was added and the mixture was stirred overnight. Since the reaction was incomplete the mixture was warmed for 30 min to 35° C. The mixture was diluted with EtOAc and extracted with 1N aqueous HCl, sat. aq. NaHCO3 and brine. After drying over Na2SO4 all volatiles were evaporated in vacuo. The product was obtained as a beige amorphous solid (89%). (ES+) m/z 501 (M+H)+.

Workup

  1. stirringthe suspension was stirred at RT
  2. stirringthe mixture was stirred overnight
  3. temperaturewas warmed for 30 min to 35° C
  4. extractionextracted with 1N aqueous HCl, sat. aq. NaHCO3 and brine
  5. dry with materialAfter drying over Na2SO4 all volatiles
  6. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-0ef0b914d42d4a56bce35e714a4dd09c
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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