Cesium carbonate → HCID 19097506, compound

HRID 486091Notes

Reaction equation

HRID 486091 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:25])([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1.Cl[CH2:29][C:30]1[S:31][CH:32]=[C:33]([CH:35]([CH3:37])[CH3:36])[N:34]=1.C([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].[NH4+].[Cl-]>CN(C=O)C>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:29][C:30]4[S:31][CH:32]=[C:33]([CH:35]([CH3:37])[CH3:36])[N:34]=4)=[CH:13][CH:14]=3)[C:9]([CH3:17])=[C:8]2[CH2:18][C:19]([CH3:24])([CH3:25])[C:20]([O:22][CH3:23])=[O:21])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15229448HCID 15229448, compoundHCID 220637012-(Chloromethyl)-4-isopropylthiazole

Product 1

HCID 19097506HCID 19097506, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (Preparation 1) (50 mg), 2-chloromethyl-4-prop-2-ylthiazole (30 mg), K2CO3 (60 mg), and Cs2CO3 (10 mg) in 2 mL DMF was stirred at room temperature under nitrogen for 24 hours. The mixture was poured onto sat.'d NH4Cl solution, extracted 2× Et2O, washed 2× brine, dried (MgSO4), and evaporated. The residue was chromatographed on silica gel (hexane/EtOAc 4:1) to give the title compound.

Workup

  1. extractionextracted 2× Et2O
  2. washwashed 2× brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-5095f42e22ea4addbab24f4abcacba56
Source dataset
uspto-grants-1994_03
Patent number
US05290798

Reaction notes

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