Cesium carbonate → (S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

HRID 449838Notes

Reaction equation

HRID 449838 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][C@@H:13]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH2:14][C:6]=3[C:5]=2[CH:4]=1)#[N:2].[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH2:29]Cl)[C:24]=1[O:31][CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH:18]([O:17][C:16](=[O:21])[NH:15][C@@H:13]1[CH2:12][C:7]2[N:8]([CH2:29][C:25]3[C:24]([O:31][CH3:32])=[C:23]([Cl:22])[CH:28]=[CH:27][N:26]=3)[C:9]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[C:6]=2[CH2:14]1)([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 118163554-chloro-2-(chloromethyl)-3-methoxypyridineHCID 66933207(S)-(7-Cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamic Acid Isopropyl Ester

Product 1

HCID 66933264(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl esterYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-isopropyl 7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate (680 mg, 2.40 mmol) and 4-chloro-2-(chloromethyl)-3-methoxypyridine (553 mg, 2.88 mmol) in dimethylformamide (5 mL) is added cesium carbonate (1.17 g, 3.60 mmol) and the mixture stirred at room temperature overnight. The reaction mixture is diluted with water and the beige solid is filtered. It is rinsed with water and then dried in a vacuum oven at 50° C. for 48 h to obtain a gray solid (970 mg, 92%). LC-ES/MS m/z 439.0 [M+H]+.

Workup

  1. filtrationthe beige solid is filtered
  2. washIt is rinsed with water
  3. customdried in a vacuum oven at 50° C. for 48 h

Sources & evidence

ORD record
ord-b2b72a8912e445fea1fc50c7d716149b
Source dataset
uspto-grants-2013_07
Patent number
US08486943B2

Reaction notes

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