Cesium carbonate → HCID 67211104, compound

HRID 2274085Notes

Reaction equation

HRID 2274085 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-21cf3a51db0c488bb3bdbcb899fb1fa6
Source dataset
uspto-grants-2015_09
Patent number
US09126932B2

Reaction notes

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