Potassium Carbonate → HCID 19603714, compound

HRID 1604672Notes

Reaction equation

HRID 1604672 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]Cl)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])=[N:22]1.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:21]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]([C:30]([O:32][CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[O:31])=[N:22]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[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:22]4[C:23]([C:30]([O:32][CH2:33][C:34]5[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=5)=[O:31])=[C:24]5[C:29]([CH:28]=[CH:27][CH:26]=[CH:25]5)=[N:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 7372664HCID 7372664, compoundHCID 19603727HCID 19603727, compound

Product 2

HCID 19603714HCID 19603714, compoundHCID 19603839HCID 19603839, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-tert-butyl-2-[5-(chloromethyl)benzofuran-2-yl]thiazole (0.36 g), benzyl indazole-3-carboxylate (0.30 g) and potassium carbonate (0.33 g) in methylethylketone (20 ml) was stirred under reflux for 7 hours. After being cooled to room temperature, the mixture was filtered and the filtrate was concentrated under reduced pressure. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of n-hexane and ethyl acetate. The fractions containing the objective compounds were combined and concentrated under reduced pressure to give benzyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-1H-indazole-3-carboxylate (0.40 g) and benzyl 2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-2H-indazole-3-carboxylate (0.12 g).

Workup

  1. temperatureunder reflux for 7 hours
  2. filtrationthe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washeluted with a mixture of n-hexane and ethyl acetate
  5. additionThe fractions containing the objective compounds
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eec12871a3b54210afa9d23cdaa9c4aa
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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