Hydrochloric Acid → HCID 19776888, compound

HRID 1612897Notes

Reaction equation

HRID 1612897 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]C)=[O:21])=[CH:4][CH:3]=1.Br[CH2:29][C:30]1[CH:39]=[CH:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:31]=1.[C:40]([O-])([O-])=O.[K+].[K+].C([O-])([O-])=O.[Cs+].[Cs+].Cl>CN(C=O)C>[CH3:40][CH:18]([C:8]1[N:7]([CH2:6][C:5]2[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:15]2[C:10]([C:9]=1[CH3:17])=[CH:11][C:12]([O:16][CH2:29][C:30]1[CH:39]=[CH:38][C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=1)=[CH:13][CH:14]=2)[C:19]([CH3:25])([CH3:24])[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 15229448HCID 15229448, compound

Product 1

HCID 19776888HCID 19776888, 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) (200 mg), 2-bromomethynaphthalene (138 mg), K2CO3 (89 mg), and Cs2CO3 (34 mg) in 5 mL DMF was stirred at room temperature under nitrogen for 24 hours. The mixture was poured onto 1N HCl, extracted 2× EtOAc, washed 2× brine, dried (MgSO4), and evaporated. Purification of the residue by chromatography (silica gel; hexane/EtOAc 4:1) gave the title compound, used as such for the next step.

Workup

  1. extractionextracted 2× EtOAc
  2. washwashed 2× brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customPurification of the residue by chromatography (silica gel; hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-b5226992b05c4919915228a94653691c
Source dataset
uspto-grants-1993_03
Patent number
US05190968

Reaction notes

Loading…