Cesium carbonate → HCID 67211104, compound

HRID 2040573Notes

Reaction equation

HRID 2040573 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=3[C:4]=2[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[N:35]=[N:36][S:37][CH:38]=2)=[CH:30][CH:29]=1>CC(N(C)C)=O>[S:37]1[CH:38]=[C:34]([C:31]2[CH:32]=[CH:33][C:28]([CH2:27][O:1][C:2]3[CH:10]=[CH:9][C:8]4[NH:7][C:6]5[CH:11]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:12][CH2:13][C:5]=5[C:4]=4[CH:3]=3)=[CH:29][CH:30]=2)[N:35]=[N:36]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27764544-(1,2,3-Thiadiazol-4-yl)benzyl bromideHCID 53345675Ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

Product 1

HCID 67211104HCID 67211104, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

In a 4 mL vial were placed ethyl 2-(7-hydroxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate (64.8 mg, 0.250 mmol), cesium carbonate (81 mg, 0.250 mmol), and 4-(4-(bromomethyl)phenyl)-1,2,3-thiadiazole (63.8 mg, 0.250 mmol). DMA (1 mL) was added and the reaction was stirred at room temperature overnight. The solid was removed by filtration and rinsed with EtOAc. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound (42.7 mg). LCMS m/z=434.2 [M+H]+.

Workup

  1. customThe solid was removed by filtration
  2. washrinsed with EtOAc
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-586040d60c684a4e8888a2cf872d6832
Source dataset
uspto-grants-2013_11
Patent number
US08580841B2

Reaction notes

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