Cesium carbonate → HCID 57859960, compound

HRID 1947121Notes

Reaction equation

HRID 1947121 reaction equation
[CH2:1]([C:3]1[N:8]([CH2:9][C:10](=[O:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7](=[O:18])[C:6]2[C:19]([O:28][CH2:29][C:30]([F:35])([F:34])[CH:31]([F:33])[F:32])=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]([CH3:22])[C:5]=2[CH:4]=1)[CH3:2].FC(F)(F)S(OCC(F)(F)C(F)F)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([C:3]1[N:8]([CH2:9][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:7](=[O:18])[C:6]2[C:19]([O:28][CH2:29][C:30]([F:34])([F:35])[CH:31]([F:32])[F:33])=[C:20]([C:23]([OH:25])=[O:24])[N:21]([CH3:22])[C:5]=2[CH:4]=1)[CH3:2].[CH2:1]([C:3]1[N:8]([CH2:9][C:10](=[O:17])[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:7](=[O:18])[C:6]2[C:19]([O:28][CH2:29][C:30]([F:34])([F:35])[CH:31]([F:33])[F:32])=[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]([CH3:22])[C:5]=2[CH:4]=1)[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 37924752,2,3,3-Tetrafluoropropyl trifluoromethanesulfonateHCID 86634217HCID 86634217, compound

Product 2

HCID 57859960HCID 57859960, compoundYield 95%HCID 86634217HCID 86634217, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In the same manner as in Reference Example 150, ethyl 6-ethyl-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-3-(2,2,3,3-tetrafluoropropoxy)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (460 mg, 93%) was obtained as a gray powder from the compound of Reference Example 40 (382 mg, 1.00 mmol), 2,2,3,3-tetrafluoropropyl trifluoromethanesulfonate (913 mg, 3.46 mmol), cesium carbonate (391 mg, 1.20 mmol) and DMF (10 mL). The title compound (310 mg, 95%) was obtained as a gray powder from the thus-obtained ethyl 6-ethyl-1-methyl-4-oxo-5-(2-oxo-2-phenylethyl)-3-(2,2,3,3-tetrafluoropropoxy)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (348 mg, 0.70 mmol) by a method similar to that in Reference Example 59.

Sources & evidence

ORD record
ord-1fee833a12394d87ac2f81812010dd57
Source dataset
uspto-grants-2013_03
Patent number
US08399449B2

Reaction notes

Loading…