Cesium carbonate → Methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-(benzothiazol-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 1032978Notes

Reaction equation

HRID 1032978 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.Br[CH2:29][C:30]1[S:31][C:32]2[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=2[N:34]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.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][C:32]5[CH:38]=[CH:37][CH:36]=[CH:35][C:33]=5[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

6

Reactant 3

HCID 10796Cesium carbonateHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 15229448HCID 15229448, compound

Product 1

HCID 19027121Methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-(benzothiazol-2-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 3-[1-(4-chlorobenzyl)-3-methyl-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (Preparation 1) (200 mg), 2-bromomethylbenzothiazole (147 mg), Cs2CO3 (263 mg) in 3 mL CH3CN and 3 mL DMF was stirred at 60° C. for 4 hours. The mixture was poured onto water, extracted with EtOAc, washed twice with brine, dried (MgSO4), and evaporated. Chromatography of the residue on silica gel eluting with hexane/EtOAc 4:1 provided the title compound as a solid.

Workup

  1. additionThe mixture was poured onto water
  2. extractionextracted with EtOAc
  3. washwashed twice with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-cb945578418c45a1aec550a7510a41c0
Source dataset
uspto-grants-1994_05
Patent number
US05308850

Reaction notes

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