Potassium Carbonate → HCID 54489686, compound

HRID 1604663Notes

Reaction equation

HRID 1604663 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([OH:29])=[CH:26][CH:27]=5)[C:22]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(=O)([O-])[O-].[K+].[K+]>CC(CC)=O>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:36][CH2:37][CH2:38][CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:26][CH:27]=5)[C:22]([CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 17928195HCID 17928195, compound

Product 1

HCID 54489686HCID 54489686, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-hydroxyindole-3-acetate (0.35 g), ethyl 5-bromopentanoate (0.232 ml) and potassium carbonate (0.31 g) in methylethylketone (5 ml) was stirred at 80° C. for 18 hours. After an insoluble mass was filtered off, the filtrate was concentrated under reduced pressure. The resulting syrup was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and n-hexane. The fractions containing the objective compound were combined and concentrated under reduced pressure. The residue was crystallized with n-hexane and the crystals were collected by filtration and washed with n-hexane to give methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]-methyl}-5-(4-ethoxycarbonylbutoxy)indole-3-acetate (0.23 g).

Workup

  1. filtrationAfter an insoluble mass was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluted with a mixture of ethyl acetate and n-hexane
  4. additionThe fractions containing the objective compound
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized with n-hexane
  7. filtrationthe crystals were collected by filtration
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-0db37a540c004ce28cc198fc0184dcbb
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

Loading…